732:. The R/S convention assigns priorities to substituents on a chiral center based on their atomic number. The highest priority group is assigned to the atom with the highest atomic number, and the lowest priority group is assigned to the atom with the lowest atomic number. The molecule is then oriented so that the lowest priority group points away from the viewer, and the remaining three groups are arranged in order of decreasing priority around the chiral center. If this arrangement is clockwise, it is assigned an R configuration; if it is counterclockwise, it is assigned an S configuration. In contrast, steroid nomenclature uses α and β to denote stereochemistry at chiral centers. The α and β designations are based on the orientation of substituents relative to each other in a specific ring system. In general, α refers to a substituent that is oriented towards the plane of the ring system, while β refers to a substituent that is oriented away from the plane of the ring system. In steroids drawn from the standard perspective used in this paper, α-bonds are depicted on figures as dashed wedges and β-bonds as solid wedges.
11004:
280:
292:
621:
80:
470:
3807:
365:
542:
12237:
2009:
1899:
2111:
1568:
1281:
12267:
12255:
12347:
12331:
12315:
12303:
12291:
1607:
12279:
443:
410:(at C-17, as shown for cholesterol) are present, the steroid is said to have a cholestane framework. The two common 5α and 5β stereoisomeric forms of steroids exist because of differences in the side of the largely planar ring system where the hydrogen (H) atom at carbon-5 is attached, which results in a change in steroid A-ring conformation. Isomerisation at the C-21 side chain produces a parallel series of compounds, referred to as isosteroids.
1627:
512:
421:
646:
527:
489:
880:
942:
354:
4204:'tetrahydro'; or creation of double (or triple) bonds, as 'didehydro', etc. In names, they are placed immediately at the front of the name of the parent hydride and in front of any nondetachable prefixes. Indicated hydrogen atoms have priority over 'hydro' prefixes for low locants. If indicated hydrogen atoms are present in a name, the 'hydro' prefixes precede them.
865:
Even though "keto" is a standard prefix in organic chemistry, the 1989 recommendations of the Joint
Commission on Biochemical Nomenclature discourage the application of the prefix "keto" for steroid names, and favor the prefix "oxo" (e.g., 11-oxo steroids rather than 11-keto steroids), because "keto"
3986:
3S‐1.4. Orientation of projection formulae. When the rings of a steroid are denoted as projections onto the plane of the paper, the formula is normally to be oriented as in 2a. An atom or group attached to a ring depicted as in the orientation 2a is termed α (alpha) if it lies below the plane of the
4166:
3S‐2.5 Unsaturation. Unsaturation is indicated by changing -ane to -ene, -adiene, -yne etc., or -an- to -en-, -adien-, -yn- etc. Examples: Androst-5-ene, not 5-androstene; 5α-Cholest-6-ene; 5β-Cholesta-7,9(11)-diene; 5α-Cholest-6-en-3β-ol. Notes. 1) It is now recommended that the locant of a double
4086:
P‐13.8.1.1 The prefix 'de' (not 'des'), followed by the name of a group or atom (other than hydrogen), denotes removal (or loss) of that group and addition of the necessary hydrogen atoms, i.e., exchange of that group with hydrogen atoms. As an exception, 'deoxy', when applied to hydroxy compounds,
3893:
3S-4. FUNCTIONAL GROUPS. 3S-4.0. General. Nearly all biologically important steroids are derivatives of the parent hydrocarbons (cf. Table 1) carrying various functional groups. Suffixes are added to the name of the saturated or unsaturated parent system (see 33-2.5), the terminal e of -ane, -ene,
3851:
3S‐1.0. Definition of steroids and sterols. Steroids are compounds possessing the skeleton of cyclopentaphenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Methyl groups are normally present at C-10 and C-13. An alkyl side chain may also be
2889:
elucidation, derivitzation or degradation chemistry, biological testing, and other research needs (generally milligrams to grams, but often more or the isolation of "analytical quantities" of the substance of interest (where the focus is on identifying and quantifying the substance (for example, in
2755:
of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of interest. At steady state, the amount of hormone entering the blood from all sources will be equal to the rate at which it
756:
carbons (generally, ones that are part of a double bond) in the steroid nucleus are indicated by changing -ane to -ene. This change was traditionally done in the parent name, adding a prefix to denote the position, with or without Δ (Greek capital delta) which designates unsaturation, for example,
4023:
P‐91.2.1.1 Cahn-Ingold-Prelog (CIP) stereodescriptors. Some stereodescriptors described in the Cahn-Ingold-Prelog (CIP) priority system, called 'CIP stereodescriptors', are recommended to specify the configuration of organic compounds, as described and exemplified in this
Chapter and applied in
2756:
is being cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating pool of steroid, then the production rate will approximate the secretion rate."
861:
groups (R-O-R), therefore, using "oxy" within the name of a steroid class may be misleading. One can find clear examples of "oxygenated" to refer to a broad class of organic molecules containing a variety of oxygen containing functional groups in other domains of organic chemistry, and it is
848:
The term "11-oxygenated" refers to the presence of an oxygen atom as an oxo (=O) or hydroxy (-OH) substituent at carbon 11. "Oxygenated" is consistently used within the chemistry of the steroids since the 1950s. Some studies use the term "11-oxyandrogens" as an abbreviation for 11-oxygenated
4203:
P-31.2.2 General methodology. 'Hydro' and 'dehydro' prefixes are associated with hydrogenation and dehydrogenation, respectively, of a double bond; thus, multiplying prefixes of even values, as 'di', 'tetra', etc. are used to indicate the saturation of double bond(s), for example 'dihydro',
4040:
770:. The double bond is designated by the lower-numbered carbon atom, i.e. "Δ-" or "4-ene" means the double bond between positions 4 and 5. The saturation of carbons of a parent steroid can be done by adding "dihydro-" prefix, i.e., a saturation of carbons 4 and 5 of testosterone with two
4024:
Chapters P‐1 through P‐8, and in the nomenclature of natural products in
Chapter P-10. The following stereodescriptors are used as preferred stereodescriptors (see P‐92.1.2): (a) 'R' and 'S', to designate the absolute configuration of tetracoordinate (quadriligant) chirality centers;
2254:
4878:
Bode HB, Zeggel B, Silakowski B, Wenzel SC, Reichenbach H, Müller R (January 2003). "Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium
Stigmatella aurantiaca".
829:
has a hydrogen atom at the 5α position (hence the "5α-" prefix), two hydroxy groups (-OH) at the 3α and 17α positions (hence "3α,17α-diol" suffix) and an oxo group (=O) at the position 20 (hence the "20-one" suffix). However, erroneous use of suffixes can be found, e.g.,
825:, while the suffix -one denotes an oxo group. When two or three identical groups are attached to the base structure at different positions, the suffix is indicated as -diol or -triol for hydroxy, and -dione or -trione for oxo groups, respectively. For example,
2746:
of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates have been assessed by sampling the venous effluent from a gland over time and subtracting out the arterial and peripheral venous hormone concentration. The
2247:
837:(the presence or absence of a number does not affect such elision). This means, for instance, that if the suffix immediately appended to the parent structure name begins with a vowel, the trailing "e" is removed from that name. An example of such removal is "
4036:
774:
atoms is 4,5α-dihydrotestosterone or 4,5β-dihydrotestosterone. Generally, when there is no ambiguity, one number of a hydrogen position from a steroid with a saturated bond may be omitted, leaving only the position of the second hydrogen atom, e.g.,
2240:
4718:
1999:
and cyclization of squalene generate lanosterol, which is the starting point for additional modifications into other steroids (steroidogenesis). In other eukaryotes, the cyclization product of epoxidized squalene (oxidosqualene) is cycloartenol.
4167:
bond is always adjacent to the syllable designating the unsaturation. 3) The use of Δ (Greek capital delta) character is not recommended to designate unsaturation in individual names. It may be used, however, in generic terms, like 'Δ-steroids'
1756:
or conceptually, from scission (cleavage) of parent steroid rings (generally one of the four). Major secosteroid subclasses are defined by the steroid carbon atoms where this scission has taken place. For instance, the prototypical secosteroid
2741:
of a steroid in the circulation is determined by the rate at which it is secreted from glands, the rate of metabolism of precursor or prehormones into the steroid, and the rate at which it is extracted by tissues and metabolized. The
4669:
The prefix oxo- should also be used in connection with generic terms, e.g., 17-oxo steroids. The term '17-keto steroids', often used in the medical literature, is incorrect because C-17 is specified twice, as the term keto denotes
1091:
765:
of a double bond to be always adjacent to the syllable designating the unsaturation, therefore, having it as a suffix rather than a prefix, and without the use of the Δ character, i.e. pregn-4-ene-11β,17α-diol-3,20-dione or
830:"5α-pregnan-17α-diol-3,11,20-trione" — since it has just one hydroxy group (at 17α) rather than two, then the suffix should be -ol, rather than -diol, so that the correct name to be "5α-pregnan-17α-ol-3,11,20-trione".
4710:
1062:
found in the cellular membranes of plants. All mushrooms contain large quantities of ergosterol, in the range of tens to hundreds of milligrams per 100 grams of dry weight. Oxygen is necessary for the synthesis of
692:
called suffixes or prefixes after the respective numbers, indicating their position in the steroid nucleus. There are widely used trivial steroid names of natural origin with significant biologic activity, such as
705:. Some of these names are defined in The Nomenclature of Steroids. These trivial names can also be used as a base to derive new names, however, by adding prefixes only rather than suffixes, e.g., the steroid
6559:
Makin HL, Honor JW, Shackleton CH, Griffiths WJ (2010). "General methods for the extraction, purification, and measurement of steroids by chromatography and mass spectrometry". In Makin HL, Gower DB (eds.).
3700:
The steroid structural base is a steran nucleus, a polycyclic C17 steran skeleton consisting of three condensed cyclohexane rings in nonlinear or phenanthrene junction (A, B, and C), and a cyclopentane ring
19354:
3947:
3S‐4.9. Trivial names of important steroids
Examples of trivial names retained for important steroid derivatives, these being mostly natural compounds of significant biological activity, are given in Table
18903:
18730:
541:
488:
4087:
denotes the removal of an oxygen atom from an –OH group with the reconnection of the hydrogen atom. 'Deoxy' is extensively used as a subtractive prefix in carbohydrate nomenclature (see P‐102.5.3).
849:
androgens, to emphasize that they all have an oxygen atom attached to carbon at position 11. However, in chemical nomenclature, the prefix "oxy" is associated with ether functional groups, i.e., a
9315:
6208:
2837:. These reactions introduce oxygen into the steroid ring, allowing the cholesterol to be broken up by other enzymes into bile acids. These acids can then be eliminated by secretion from the
3507:"Recherches chimiques sur les corps gras, et particulièrement sur leurs combinaisons avec les alcalis. Sixième mémoire. Examen des graisses d'homme, de mouton, de boeuf, de jaguar et d'oie"
5028:
Bhetariya PJ, Sharma N, Singh P, Tripathi P, Upadhyay SK, Gautam P (21 March 2017). "Human Fungal
Pathogens and Drug Resistance Against Azole Drugs". In Arora C, Sajid A, Kalia V (eds.).
2913:, are chosen to be "orthogonal"—achieving their separations based on distinct modes of interaction between substance and isolating matrix—to detect a single species in the pure sample.
18689:
17869:
17852:
17095:
14751:
14746:
6416:
Zollner G, Marschall HU, Wagner M, Trauner M (2006). "Role of nuclear receptors in the adaptive response to bile acids and cholestasis: pathogenetic and therapeutic considerations".
17823:
9666:
9310:
893:
to examine this and the following section (and throughout), and to remove redundancies of listed content, and to ensure sourcing for the listed content that remains in any section.
19834:
18644:
9422:
8694:
2794:
845:" is dropped due to the vowel ("o") at the beginning of the suffix -ol. Some authors incorrectly use this rule, eliding the terminal "e" where it should be kept, or vice versa.
17141:
12456:
11359:
1768:(shown), is in the 9,10-secosteroid subclass and derives from the cleavage of carbon atoms C-9 and C-10 of the steroid B-ring; 5,6-secosteroids and 13,14-steroids are similar.
19829:
14169:
7019:
6534:
4359:
Bongiovanni AM, Clayton GW (March 1954). "Simplified method for estimation of 11-oxygenated neutral 17-ketosteroids in urine of individuals with adrenocortical hyperplasia".
4284:
3509:[Chemical research on fatty substances, and particularly on their combinations with alkalis. Sixth memoir. Examination of human, sheep, beef, jaguar and goose fats].
17989:
16632:
12710:
9671:
442:
17030:
511:
303:
5α-dihydroprogesterone (5α-DHP), a steroid. The shape of the four rings of most steroids is illustrated (carbon atoms in black, oxygens in red and hydrogens in grey). The
9295:
6714:
Fried J, Thoma RW, Gerke JR, Herz JE, Donin MN, Perlman D (1952). "Microbiological
Transformations of Steroids.1 I. Introduction of Oxygen at Carbon-11 of Progesterone".
750:
atoms in the steroid nucleus is set in a template found in the
Nomenclature of Steroids that is used regardless of whether an atom is present in the steroid in question.
14332:
1107:
18735:
2197:
Estradiol is converted from testosterone directly (in males), or via the primary pathway DHEA – androstenedione – estrone and secondarily via testosterone (in females).
19276:
12700:
18938:
18765:
17857:
17655:
17277:
17187:
10786:
9032:
8983:
13024:
4529:
Barnard L, du Toit T, Swart AC (April 2021). "Back where it belongs: 11β-hydroxyandrostenedione compels the re-assessment of C11-oxy androgens in steroidogenesis".
2919:
refers to the methods to determine the chemical structure of an isolated pure steroid, using an evolving array of chemical and physical methods which have included
18760:
17806:
17794:
17597:
17255:
17182:
16864:
16204:
9475:
7177:
1261:
and synthetic, which interact with androgen receptors to increase muscle and bone synthesis. In popular use, the term "steroids" often refers to anabolic steroids.
4310:
1078:. Provitamin D2 spontaneously forms vitamin D2. However, not all fungi utilize ergosterol in their cellular membranes; for example, the pathogenic fungal species
18161:
18011:
17886:
17481:
17349:
8978:
19679:
19233:
17818:
17777:
17250:
17238:
14683:
12398:
8908:
3518:
613:
has two methyl groups at C-4. Cholesterol which has a C-5 to C-6 double bond, differs from testosterone and progesterone which have a C-4 to C-5 double bond.
19539:
18718:
18043:
17694:
17609:
17337:
17124:
1883:, steroids are highly concentrated energy stores. However, they are not typically sources of energy; in mammals, they are normally metabolized and excreted.
5886:
Lees ND, Skaggs B, Kirsch DR, Bard M (March 1995). "Cloning of the late genes in the ergosterol biosynthetic pathway of
Saccharomyces cerevisiae—a review".
4688:
17898:
17170:
6501:
4813:
2970:
is key when producing the wide variety of medications available within this chemical classification. These modifications are performed using conventional
19509:
18637:
17994:
8687:
20647:
18528:
17672:
9192:
6204:
378:, also known as steran or cyclopentanoperhydrophenanthrene, the simplest steroid and the nucleus of all steroids and sterols, is composed of seventeen
16779:
14146:
9646:
2132:
of steroidogenesis differ among species. The major classes of steroid hormones, as noted above (with their prominent members and functions), are the
20140:
12830:
18601:
17023:
16545:
9122:
7331:
7215:
5229:
71:
14736:
2931:
overlap both of the above areas, emphasizing analytical methods to determining if a steroid is present in a mixture and determining its quantity.
19644:
16596:
16588:
8918:
19459:
19269:
18630:
18606:
18553:
18443:
18121:
16171:
13718:
13708:
8913:
8680:
7474:
7348:
4608:
Barrientos EJ, Lapuerta M, Boehman AL (August 2013). "Group additivity in soot formation for the example of C-5 oxygenated hydrocarbon fuels".
3441:
983:
cells, which include animals, plants, fungi, and protists, have complex cellular structures with a true nucleus and membrane-bound organelles.
783:. The Δ-steroids are those with a double bond between carbons 5 and 6 and the Δ steroids are those with a double bond between carbons 4 and 5.
6969:
6943:
6917:
6865:
6839:
6813:
1051:, inducing depletion of ergosterol, or mutations that decrease the ergosterol content) to develop resistance to drugs that target ergosterol.
19203:
18448:
18433:
16931:
16926:
16424:
16419:
16414:
16284:
14151:
8988:
7338:
6891:
5284:
18114:
2857:
when there is a high blood concentration of steroids. Steroid hormones, lacking the side chain of cholesterol and bile acids, are typically
2152:
Progestogens are the precursors of all other human steroids, and all human tissues which produce steroids must first convert cholesterol to
19063:
16890:
16810:
16607:
15909:
15693:
14192:
14187:
13972:
13748:
13738:
10502:
9005:
7273:
1847:, leading to coral mortality from black coral disease. Nakiterpiosin-type steroids are active against the signaling pathway involving the
526:
420:
15396:
3288:
20707:
20702:
20692:
20687:
20682:
20677:
20672:
20642:
20637:
20632:
20578:
20558:
20538:
20533:
20528:
20503:
20413:
20408:
20403:
20393:
19238:
19208:
18898:
18508:
18503:
18498:
17016:
16682:
16677:
16449:
16374:
14491:
14426:
14421:
14371:
14202:
14116:
13728:
2910:
5377:"IUPAC Recommendations: Skeletal Modification in Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999)"
1786:; "same", indicating carbon addition) are structural subclasses of steroids formed from biosynthetic steps. The former involves enzymic
20833:
20518:
20451:
19133:
19128:
19093:
19088:
19083:
19068:
18468:
18356:
18343:
18178:
17376:
16657:
16652:
16499:
16494:
14846:
14676:
14486:
14361:
14312:
14136:
14121:
14052:
13763:
13673:
12391:
9239:
3572:
20588:
19262:
19158:
18428:
18423:
16992:
16825:
16820:
16504:
16339:
16294:
15643:
14645:
13952:
13947:
13937:
13778:
13608:
3960:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-1.4".
1956:
pathway which produces steroids from simple precursors. A unique biosynthetic pathway is followed in animals (compared to many other
1949:. Lanosterol and cycloartenol are sometimes called protosterols because they serve as the starting compounds for all other steroids.
833:
According to the rule set in the
Nomenclature of Steroids, the terminal "e" in the parent structure name should be elided before the
729:
17325:
7015:
6526:
5380:
18792:
17214:
16662:
16570:
16565:
16555:
16469:
16394:
15406:
14481:
14302:
13653:
12251:
Single lines: pathways common to most lifeforms. Double lines: pathways not in humans (occurs in e.g. plants, fungi, prokaryotes).
9601:
7111:
Han TS, Walker BR, Arlt W, Ross RJ (February 2014). "Treatment and health outcomes in adults with congenital adrenal hyperplasia".
4280:
3907:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-4.9"
1988:
18701:
17728:
17631:
17539:
17527:
17107:
20498:
18865:
17585:
17425:
16509:
14650:
13130:
10974:
8903:
5980:
Roelofs AJ, Thompson K, Gordon S, Rogers MJ (October 2006). "Molecular mechanisms of action of bisphosphonates: current status".
5598:"Paracrine Sonic Hedgehog Signaling Contributes Significantly to Acquired Steroidogenesis in the Prostate Tumor Microenvironment"
2909:. In both cases, the isolated substance is purified to chemical homogeneity; combined separation and analytical methods, such as
568:(cleavage and reclosing to a larger or smaller rings)—all variations in the carbon-carbon bond framework—steroids can also vary:
469:
4791:
3343:
2128:
Steroidogenesis is the biological process by which steroids are generated from cholesterol and changed into other steroids. The
1987:(FPP), which further conjugates with each other to form the linear triterpenoid squalene. Squalene biosynthesis is catalyzed by
18877:
17437:
16185:
13643:
3222:
1084:
does not, which has important clinical implications (given the mechanism of action of many antifungal drugs). Using the fungus
9917:
3934:
1717:
In biology, it is common to name the above steroid classes by the number of carbon atoms present when referring to hormones: C
993:(the emergence of modern eukaryotic cells), steroids likely played a role in the acquisition of mitochondria via endocytosis.
826:
20880:
20843:
20838:
16987:
14669:
14640:
13592:
12384:
7166:
7052:
7005:
6758:
6698:
6569:
6251:
5577:
5544:
5478:
5260:
5168:
5143:
5075:
5037:
4589:
4196:
4079:
4016:
3726:
3693:
3657:
3379:
3114:
2890:
biological tissue or fluid). The amount isolated depends on the analytical method, but is generally less than one microgram.
12725:
62:
This article is about the family of polycyclic compounds. For the drugs, also used as performance-enhancing substances, see
19449:
16982:
15478:
14956:
14635:
12631:
10366:
8746:
7654:
7208:
5792:
16716:
12980:
8751:
6273:
5931:"Rosuvastatin, inflammation, C-reactive protein, JUPITER, and primary prevention of cardiovascular disease—a perspective"
5091:
Wink M (September 2003). "Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective".
753:
7185:
19925:
14941:
14936:
13387:
13382:
8633:
6130:"The glucocorticoid-activating enzyme 11β-hydroxysteroid dehydrogenase type 1 catalyzes the activation of testosterone"
5596:
Lubik AA, Nouri M, Truong S, Ghaffari M, Adomat HH, Corey E, Cox ME, Li N, Guns ES, Yenki P, Pham S, Buttyan R (2016).
4306:
1964:
and other anti-infection drugs. Steroid metabolism in humans is also the target of cholesterol-lowering drugs, such as
896:
87:, a prototypical steroid with 32 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with
12820:
5435:
2818:
2789:
During diseases pathways otherwise not significant in healthy humans can become utilized. For example, in one form of
19634:
18740:
18258:
14989:
13049:
12626:
9465:
4643:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
4140:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
4099:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
3867:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
3825:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
3308:"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989".
1992:
838:
19454:
18193:
13832:
3506:
3480:
20200:
19389:
15005:
14231:
13136:
13099:
12929:
12894:
9872:
9596:
8898:
4924:"Phylogenomics of sterol synthesis: insights into the origin, evolution, and diversity of a key eukaryotic feature"
3254:
20135:
19799:
18513:
17500:
15560:
15126:
12825:
9621:
2751:
of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The
1603:
performs this classification is available at the Knowledge MeSH catalog. Examples of this classification include:
986:
Steroids are integral to eukaryotic cellular membranes, where they help maintain membrane integrity and function.
16140:
13054:
11301:
10497:
7201:
6295:
Lichtenthaler HK (June 1999). "The 1-deoxy-d-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants".
4682:
3395:
Rhen T, Cidlowski JA (October 2005). "Antiinflammatory action of glucocorticoids--new mechanisms for old drugs".
2850:
19930:
19334:
15200:
15168:
9281:
9080:
6493:
3894:-yne, -adiene etc. being elided before a vowel (presence or absence of numerals has no effect on such elisions).
3552:, de χολη, bile, et στερεος, solide, la substance cristallisée des calculs biliares humains, ... " (I will name
1825:
migration of the original C-13 atom. Ingestion of these C-nor-D-homosteroids results in birth defects in lambs:
866:
includes the carbon that is part of the steroid nucleus and the same carbon atom should not be specified twice.
20848:
20721:
19674:
15391:
12584:
10223:
9857:
9571:
9232:
8893:
2790:
18908:
13822:
10574:
6101:
5647:"Methanocaldococcus jannaschii uses a modified mevalonate pathway for biosynthesis of isopentenyl diphosphate"
3852:
present at C-17. Sterols are steroids carrying a hydroxyl group at C-3 and most of the skeleton of cholestane.
20731:
10900:
10168:
3212:
3192:
1048:
12491:
12471:
9591:
9536:
579:
in the number of methyl groups attached to the ring (and, when present, on the prominent side chain at C17),
20828:
20155:
20037:
19804:
19704:
19669:
19228:
18993:
18596:
16977:
15291:
14630:
14600:
14165:
13459:
12847:
12007:
11003:
8844:
8110:
1470:
1412:
767:
19404:
16741:
14851:
14826:
13320:
12673:
12486:
11147:
11136:
10208:
10203:
9531:
6782:
Marker RE, Rohrmann E (1939). "Sterols. LXXXI. Conversion of Sarsasa-Pogenin to Pregnanedial—3(α),20(α)".
3164:— In part, for developing methods to determine the stereochemical course of cholesterol biosynthesis from
1821:, two of a sub-family of steroids where the C- and D-rings are contracted and expanded respectively via a
20263:
20205:
19699:
19664:
19544:
18278:
16997:
15239:
13537:
12899:
12501:
10967:
9686:
8928:
8823:
8795:
8660:
7632:
6645:
Hesselink PG, van Vliet S, de Vries H, Witholt B (1989). "Optimization of steroid side chain cleavage by
3093:
2027:
1973:
1907:
758:
20478:
20473:
17080:
13522:
13517:
13325:
10093:
9347:
6169:
Rossier MF (August 2006). "T channels and steroid biosynthesis: in search of a link with mitochondria".
5696:"Physiology and Pathophysiology of Steroid Biosynthesis, Transport and Metabolism in the Human Placenta"
5225:
1043:
fungi. Fungi can alter their ergosterol content (e.g. through loss of function mutations in the enzymes
19920:
18664:
18653:
17510:
15244:
13059:
12678:
12181:
12056:
11583:
10407:
10123:
10014:
9521:
3770:
3264:
2783:
746:(hence "deoxy") attached to position 11 (as a part of a hydroxy group). The numbering of positions of
256:. Steroids can also be more radically modified, such as by changes to the ring structure, for example,
42:
20772:
19469:
19364:
19359:
19349:
18928:
18923:
18725:
18198:
13827:
10328:
10323:
9999:
9994:
9989:
9984:
9460:
9397:
9392:
9300:
4402:
Slaunwhite Jr WR, Neely L, Sandberg AA (1964). "The metabolism of 11-Oxyandrogens in human subjects".
2798:
1968:. In humans and other animals the biosynthesis of steroids follows the mevalonate pathway, which uses
706:
20195:
19889:
19514:
16299:
16209:
15431:
12889:
12616:
12562:
12086:
11767:
11329:
11316:
11039:
10771:
10693:
10448:
9225:
9157:
9090:
8923:
8818:
8813:
8654:
6996:
Russel CA (2005). "Organic Chemistry: Natural products, Steroids". In Russell CA, Roberts GK (eds.).
5163:. Portland (Oregon USA) and Salusbury (London England): Timber press inc. pp. 324, 325 and 326.
5138:. Portland (Oregon USA) and Salusbury (London England): Timber press inc. pp. 252, 253 and 254.
3217:
3202:
2031:
1977:
1903:
1852:
1488:
38:
20757:
20752:
19474:
19409:
19324:
19319:
18403:
12668:
10103:
10098:
10088:
10083:
10004:
9631:
6066:"Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis"
5504:"Recent aspects of chemical ecology: Natural toxins, coral communities, and symbiotic relationships"
3502:
3449:
780:
776:
316:
20383:
20150:
20070:
20026:
18684:
17158:
17090:
17075:
16860:
16622:
16535:
16160:
15853:
15386:
15381:
15281:
13479:
13448:
13168:
13109:
12842:
12620:
12496:
12446:
11744:
11454:
11241:
10791:
10512:
10453:
10359:
10163:
10034:
9696:
9656:
9470:
9445:
9342:
8784:
7647:
7065:"A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids"
6231:
3082:
1600:
1086:
17:
19464:
19329:
18918:
13817:
13552:
13532:
10318:
9927:
9440:
8672:
6887:
5276:
4281:"Google Scholar search results for "5α-pregnan-17α-diol-3,11,20-trione" that is an incorrect name"
3682:"Anabolic Androgenic Steroids: Structure, Nomenclature, and Classification, Biological Properties"
20145:
19945:
19789:
19744:
19619:
19243:
18816:
18611:
18104:
17910:
17660:
17301:
17289:
17050:
17039:
16148:
16058:
15683:
15673:
15608:
15136:
14906:
14348:
13275:
12837:
12737:
12335:
12323:
12259:
11981:
11726:
10885:
10634:
10629:
10615:
10590:
9912:
9757:
8862:
3255:
Moss GP, the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature (1989).
1833:
and leg deformity from veratramine. A further C-nor-D-homosteroid (nakiterpiosin) is excreted by
1074:
content found in mushrooms; ergosterol is chemically converted into provitamin D2 by exposure to
108:
14946:
14921:
14861:
14856:
13019:
4233:"The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders"
4125:
3S-1.1. Numbering and ring letters. Steroids are numbered and rings are lettered as in formula 1
20762:
20165:
20066:
19739:
19534:
19494:
19344:
19339:
18696:
18134:
Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids):
18050:
18023:
17755:
17454:
17102:
16116:
15668:
15148:
15073:
15068:
15021:
14340:
13475:
13114:
12985:
12857:
12705:
12574:
12523:
12209:
11426:
11224:
10960:
10920:
10854:
10740:
10735:
10440:
10218:
10128:
10064:
10009:
9852:
9651:
9566:
9455:
9352:
9305:
9272:
9071:
8951:
8881:
8710:
8065:
6965:
6939:
6913:
6861:
6835:
6809:
3256:
3130:
3012:
2959:
2894:
2775:
2219:
1984:
1479:
1444:
1198:
1080:
18913:
14876:
13812:
9132:
3714:
3556:– from χολη (bile) and στερεος (solid) – the crystalized substance from human gallstones ... )
3541:
1890:, where steroid production inside and outside the tumour promotes cancer cell aggressiveness.
1736:
The gonane (steroid nucleus) is the parent 17-carbon tetracyclic hydrocarbon molecule with no
1580:
1428:, which contributes to the development and maintenance of female secondary sex characteristics
1293:
19970:
19774:
19659:
19529:
19296:
19285:
18208:
18203:
18092:
17979:
17922:
17847:
17740:
17643:
17561:
16389:
16214:
16152:
15678:
15222:
15185:
15173:
15041:
13872:
13360:
13210:
13104:
12769:
12451:
12307:
11837:
11611:
11473:
10925:
10890:
10846:
10610:
10469:
10118:
9907:
9827:
9259:
8839:
8808:
7912:
4307:"Google Scholar search results for "5α-pregnane-17α-ol-3,20-dione" that is an incorrect name"
3596:"Conformations of Steroid Hormones: Infrared and Vibrational Circular Dichroism Spectroscopy"
3136:
3118:
3086:
3026:
2955:
1911:
1292: with: A more detailed explanation of function would also be beneficial. You can help by
1044:
954:
586:
387:
17085:
14951:
14926:
14901:
14886:
14821:
14761:
14756:
9807:
9802:
9641:
9636:
9417:
5404:"Recent developments in the isolation and synthesis of D-homosteroids and related compounds"
3568:
20348:
20302:
20284:
20259:
20116:
20062:
20047:
20022:
19854:
19729:
19629:
19574:
19048:
19033:
19013:
18943:
18328:
17699:
17573:
17449:
17388:
15809:
15466:
15205:
15111:
15053:
14831:
14032:
13500:
13471:
13444:
13310:
13198:
13007:
12975:
12941:
12579:
12550:
12283:
11832:
11108:
11093:
10864:
10569:
10545:
10507:
10293:
10153:
9701:
9661:
9142:
9037:
9015:
7938:
6598:
5100:
4984:
4617:
3227:
2262:
Production rates, secretion rates, clearance rates, and blood levels of major sex hormones
2123:
2114:
Human steroidogenesis, with the major classes of steroid hormones, individual steroids and
2089:
1791:
1027:, which are involved in maintaining the integrity of the fungal cellular membrane. Various
14891:
14766:
14741:
12663:
10178:
9837:
9832:
9626:
9616:
7155:
Recent Progress in Hormone Research: Proceedings of the 1979 Laurentian Hormone Conference
6232:"The Hypothalamic–Pituitary–Ovarian Axis and Oral Contraceptives: Regulation and Function"
3811:
3806:
3681:
3157:— Development of the concept of conformation in chemistry, emphasizing the steroid nucleus
3107:— Isolation and structural studies of steroid sex hormones, and related studies on higher
2203:
have been shown to produce steroids in response to signaling produced by androgen-starved
2156:. This conversion is the rate-limiting step of steroid synthesis, which occurs inside the
1579: with: a more full discussion of this most prominent structural type. You can help by
279:
8:
20002:
19869:
19849:
19844:
19694:
19594:
19584:
19554:
19489:
18933:
18438:
18323:
18228:
18218:
17750:
17488:
17313:
16870:
16785:
15849:
15633:
15490:
15456:
15266:
14966:
14555:
14550:
14282:
14242:
14087:
14007:
13907:
13897:
13842:
13422:
12958:
12715:
12569:
12466:
12126:
11886:
11860:
11576:
10809:
10428:
10352:
10333:
10053:
9960:
9942:
9932:
9902:
9576:
9561:
9526:
9362:
7640:
5376:
2802:
1864:
1799:
1483:
1474:
761:(also Δ-androstene-3,11,17-trione). However, the Nomenclature of Steroids recommends the
123:
18622:
14881:
6602:
5864:
5756:
Kuzuyama T, Seto H (April 2003). "Diversity of the biosynthesis of the isoprene units".
5104:
4988:
4621:
3810: This article incorporates text from this source, which is available under the
2893:
The methods of isolation to achieve the two scales of product are distinct, but include
959:
Please expand the section to include this information. Further details may exist on the
520:, a steroid hormone involved in the female menstrual cycle, pregnancy, and embryogenesis
20548:
20488:
20468:
20318:
20298:
20215:
19809:
19754:
19719:
19609:
19564:
19504:
19288:
18828:
18745:
18656:
18548:
18418:
18390:
18253:
17835:
17371:
17042:
16952:
16736:
16617:
16199:
15813:
15473:
15131:
15048:
14993:
14836:
14796:
14786:
14726:
14695:
13392:
13255:
13215:
13193:
13126:
13029:
13002:
12970:
12803:
12693:
12545:
12410:
12339:
12249:. Click any text (name of pathway or metabolites) to link to the corresponding article.
11643:
11604:
11550:
11413:
10932:
10605:
10550:
10537:
9956:
9952:
9882:
9792:
9777:
9762:
9691:
8718:
7136:
7089:
7064:
6764:
6358:
6331:
6093:
6005:
5957:
5930:
5911:
5823:
5730:
5695:
5671:
5646:
5627:
5484:
5202:
5185:
5005:
4972:
4948:
4923:
4904:
4855:
4828:
4768:
4741:
4656:
4629:
4554:
4506:
4481:
4457:
4430:
4384:
4257:
4232:
4153:
4112:
3973:
3922:
3880:
3838:
3795:
3622:
3595:
3420:
3321:
3280:
3017:
2886:
2077:
2017:
1834:
668:
Almost all biologically relevant steroids can be presented as a derivative of a parent
67:
18398:
17136:
16540:
14816:
10198:
10193:
9867:
6619:
6586:
5319:
5112:
4345:
739:" is an example of a derived name that uses cortisol as a parent structure without an
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20210:
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18804:
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18283:
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5815:
5773:
5735:
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5676:
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5358:
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5256:
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5164:
5139:
5116:
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5010:
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4511:
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4429:
Taylor AE, Ware MA, Breslow E, Pyle L, Severn C, Nadeau KJ, et al. (July 2022).
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4192:
4157:
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1135:
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728:
of organic chemistry to denote absolute configuration of functional groups, known as
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142:
119:
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10344:
10246:
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10183:
9752:
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6308:
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5488:
4908:
3647:
3446:
Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology
3284:
1902:
Simplification of the end of the steroid synthesis pathway, where the intermediates
20777:
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20255:
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19254:
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5707:
5666:
5658:
5631:
5609:
5515:
5466:
5425:
5415:
5350:
5315:
5277:"C19-steroid hormone biosynthetic pathway – Ontology Browser – Rat Genome Database"
5197:
5108:
5000:
4992:
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4935:
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4763:
4753:
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4625:
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4411:
4388:
4368:
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4004:
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3834:
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3607:
3424:
3404:
3317:
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3197:
2967:
2118:
pathways. Changes in molecular structure from a precursor are highlighted in white.
1886:
Steroids play critical roles in a number of disorders, including malignancies like
1782:; "normal" in chemistry, indicating carbon removal) and homosteroids (homo-, Greek
1599:
Steroids can be classified based on their chemical composition. One example of how
1462:
1453:
1313:
1254:
1171:
1028:
736:
689:
677:
565:
554:, with a fully branched hydrocarbon side chain at C-17 and an hydroxyl group at C-3
434:
217:
100:
63:
14911:
13557:
9742:
6681:
Sandow J, Jürgen E, Haring M, Neef G, Prezewowsky K, Stache U (2000). "Hormones".
6610:
6128:
Oestlund I, Snoep J, Schiffer L, Wabitsch M, Arlt W, Storbeck KH (February 2024).
6097:
5993:
4574:
Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013
4181:
Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013
4064:
Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013
4001:
Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013
620:
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15966:
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14102:
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13295:
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12195:
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11013:
10781:
10663:
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10228:
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9681:
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8286:
8244:
7752:
7398:
7373:
7368:
7290:
7285:
7150:
5458:
5420:
5306:
Edgren RA, Stanczyk FZ (December 1999). "Nomenclature of the gonane progestins".
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3100:
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1939:
1887:
1758:
1610:
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1224:
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1143:
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about non-eukaryotic type sterol framework – see PMID 27446030, fig 4/5, group 1
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717:
547:
456:
369:
320:
241:
181:
79:
16070:
16066:
16044:
6243:
6146:
6129:
5793:"An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants"
2814:
2226:
required for the local synthesis of pregnenolone, progesterone, DHEA and DHEAS,
2065:. Lanosterol can then be converted into other steroids, such as cholesterol and
757:
4-pregnene-11β,17α-diol-3,20-dione (also Δ-pregnene-11β,17α-diol-3,20-dione) or
20368:
20328:
20274:
20240:
20220:
20175:
20101:
20096:
20057:
20052:
20017:
19734:
19424:
19103:
19053:
19028:
19018:
18973:
18963:
18948:
18860:
18787:
18776:
18755:
17650:
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17544:
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17198:
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16592:
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15893:
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15585:
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15321:
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15251:
15153:
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14871:
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14062:
13887:
13862:
13490:
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13439:
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13163:
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12776:
12719:
12658:
12653:
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12295:
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12063:
11993:
11657:
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11164:
11123:
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10776:
10766:
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10703:
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10251:
10113:
9817:
9546:
9485:
9377:
9334:
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7358:
6182:
5831:
4833:
Proceedings of the National Academy of Sciences of the United States of America
4746:
Proceedings of the National Academy of Sciences of the United States of America
3594:
Yang Y, Krin A, Cai X, Poopari MR, Zhang Y, Cheeseman JR, Xu Y (January 2023).
3165:
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815:
811:
725:
598:
561:
479:
460:
383:
104:
13402:
7494:
7489:
7016:"Russell Marker Creation of the Mexican Steroid Hormone Industry - Landmark -"
6750:
6267:
5470:
4675:
4542:
4497:
4372:
3612:
2876:
1802:
precursors with more (or fewer) ring atoms than the parent steroid framework.
20869:
20697:
20593:
20493:
20398:
20225:
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19935:
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19654:
19524:
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18855:
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17551:
17534:
17522:
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17505:
17415:
17410:
17344:
17262:
16444:
16279:
16254:
16034:
15952:
15785:
15763:
15618:
15495:
15227:
15078:
15036:
14471:
14416:
14391:
13967:
13365:
13265:
12476:
11853:
11799:
11776:
11735:
11627:
11618:
11499:
11254:
10730:
10417:
10039:
9541:
9137:
8766:
8582:
8548:
8543:
8494:
7724:
7484:
7479:
7469:
7326:
6690:
6381:
Pikuleva IA (December 2006). "Cytochrome P450s and cholesterol homeostasis".
6050:
5721:
5712:
5554:
5520:
5503:
5341:
Hanson JR (June 2010). "Steroids: partial synthesis in medicinal chemistry".
4447:
3187:
3182:
3042:
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2963:
2858:
2200:
2157:
1872:
1867:
molecules (the most notable examples are steroid hormones), and steroids and
1837:
1236:
1127:
1000:, biosynthetic pathways exist for the tetracyclic steroid framework (e.g. in
822:
710:
475:
395:
257:
249:
199:
150:
115:
114:
Steroids have two principal biological functions: as important components of
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7098:
6478:
6453:"The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism"
6437:
6402:
6367:
6316:
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6155:
6089:
6001:
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3448:. International Union Of Biochemistry And Molecular Biology. Archived from
3416:
3150:
3126:
2779:
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2022:
The mevalonate pathway (also called HMG-CoA reductase pathway) begins with
1935:
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177:
173:
138:
18697:
11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
17103:
11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
7662:
7044:
6348:
5907:
5872:
5463:
Total synthesis of natural products: at the frontiers of organic chemistry
4664:
4581:
4188:
4161:
4120:
4071:
4008:
3981:
3930:
3888:
3846:
3329:
2801:(17-OHP) – this pathological excess of 17-OHP in turn may be converted to
2148:. Human steroidogenesis of these classes occurs in a number of locations:
1805:
Combinations of these ring alterations are known in nature. For instance,
1729:-steroids for the pregnanes (mostly corticosteroids). The classification "
364:
224:(cyclopentanoperhydrophenanthrene). It is typically composed of seventeen
20627:
20373:
20343:
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20032:
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6745:. Prague: Academia Publishing House of Czechoslovak Academy of Sciences.
6628:
6469:
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4996:
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4248:
3472:
3408:
3089:— Constitution of bile acids and sterols and their connection to vitamins
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2885:, depending on context, is the isolation of chemical matter required for
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130:
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6498:
WHO Collaborating Centre in Education and Research in Human Reproduction
5947:
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15755:
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15603:
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14197:
14092:
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13618:
13577:
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13285:
13235:
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12759:
12611:
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12014:
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10561:
10493:
10436:
10379:
10375:
10303:
9747:
9248:
9197:
9177:
9147:
9109:
9027:
9000:
8993:
8973:
8966:
8854:
8736:
8553:
8471:
8397:
8356:
8344:
8339:
8225:
8215:
8009:
8004:
7957:
7621:
7600:
7556:
7321:
7314:
7104:
5899:
5811:
3154:
3144:
3050:
2947:
2940:
2898:
2073:
2066:
2062:
2050:
2023:
1969:
1961:
1943:
1931:
1919:
1848:
1771:
1762:
1690:
1651:
1546:
1502:
1232:
1170:(controlling molting in some species). Vertebrate examples include the
1155:
1123:
1099:
1095:
1064:
1040:
1024:
1009:
858:
713:(-OH) at position 17 of the steroid nucleus comparing to progesterone.
685:
650:
610:
573:
501:
precursor to animal steroids. The number of carbons (30) indicates its
494:
407:
315:
groups at opposing ends (red) are common features of natural steroids.
265:
253:
232:
rings (rings A, B and C in the first illustration) and one five-member
185:
169:
15401:
14896:
9217:
7080:
6429:
5614:
5597:
1058:
found in the cellular membranes of animals (including humans), or the
609:
have a carbonyl (oxo substituent) at C-3. Among these compounds, only
20433:
20423:
20353:
20333:
20308:
20275:
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
20185:
20160:
20007:
19997:
19965:
19950:
19904:
19859:
19814:
19759:
19709:
19484:
19434:
19374:
19058:
19023:
18983:
18953:
18799:
18268:
18173:
18151:
18099:
17944:
17466:
17366:
17267:
17233:
17221:
17148:
16895:
16875:
16815:
16795:
16637:
16474:
16349:
16344:
16329:
16314:
16274:
16156:
16124:
16082:
16030:
16026:
16022:
16012:
15992:
15976:
15925:
15901:
15897:
15885:
15877:
15873:
15833:
15821:
15805:
15791:
15781:
15777:
15733:
15593:
15567:
15555:
15530:
15520:
15505:
15485:
15436:
15336:
15331:
15306:
15296:
15261:
15121:
15096:
15058:
15016:
14586:
14560:
14540:
14536:
14524:
14401:
14366:
14307:
14267:
14262:
14161:
14141:
14077:
14042:
14017:
14012:
13997:
13917:
13867:
13788:
13723:
13668:
13658:
13648:
13582:
13429:
13417:
13173:
13064:
12992:
12953:
12879:
12852:
12781:
12535:
12518:
12119:
12104:
12095:
11973:
11963:
11951:
11938:
11924:
11913:
11909:
11878:
11873:
11866:
11825:
11387:
10832:
10639:
10383:
10288:
10236:
9727:
9387:
9182:
8180:
8089:
8042:
7973:
7813:
7668:
7537:
5769:
5535:
Silverthorn DU, Johnson BR, Ober WC, Ober CE, Silverthorn AC (2016).
5354:
5186:"Steroids: pharmacology, complications, and practice delivery issues"
3207:
3140:
3022:
3004:
2573:
2397:
2046:
2008:
1953:
1534:
1458:
1425:
1419:
1402:
1395:
1071:
1005:
980:
925:
628:
452:
394:
rings (A, B, and C in the first illustration) form the skeleton of a
360:, the simplest steroid, consisting only of the common steroid nucleus
134:
84:
14841:
12363:
1938:(in other eukaryotes). Both lanosterol and cycloartenol derive from
20568:
20523:
20126:
20121:
19879:
19519:
19419:
19414:
19113:
18772:
18713:
18538:
18338:
18238:
18183:
17984:
17667:
17194:
17119:
16766:
16756:
16459:
16319:
16239:
16234:
16167:
15984:
15921:
15917:
15881:
15869:
15841:
15837:
15825:
15817:
15747:
15535:
15525:
15371:
15356:
15341:
15276:
15271:
15116:
15026:
14572:
14451:
14446:
14441:
14436:
14431:
14237:
13992:
13927:
13743:
13698:
13693:
13688:
13683:
13678:
13633:
13572:
13567:
13507:
12688:
12530:
12142:
11946:
11820:
11813:
11590:
9722:
9711:
9513:
9490:
9382:
8956:
8867:
8702:
8524:
8509:
8481:
8410:
8376:
8175:
8047:
7948:
7922:
7907:
7858:
7848:
7808:
7733:
7672:
7447:
7440:
6065:
5694:
Chatuphonprasert W, Jarukamjorn K, Ellinger I (12 September 2018).
5693:
5379:. International Union of Pure and Applied Chemistry (IUPAC). 1999.
3169:
2183:
2145:
2141:
2100:), which are used to treat a number of bone-degenerative diseases.
2058:
2038:
1957:
1946:
1915:
1898:
1826:
1810:
1677:
1332:
1210:
1206:
1183:
1131:
1119:
928:. In eukaryotes, steroids are found in fungi, plants, and animals.
917:
842:
771:
702:
681:
304:
188:
20452:
18685:
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
18357:
17091:
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
9446:
11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
3543:
Annales de chimie et de physique (Annals of Chemistry and Physics)
3511:
Annales de Chimie et de Physique (Annals of Chemistry and Physics)
2110:
1606:
582:
in the functional groups attached to the rings and side chain, and
20388:
20363:
20358:
20279:
19955:
19078:
19073:
18313:
18223:
16921:
16667:
16479:
16379:
16369:
16364:
16144:
16078:
15970:
15845:
15653:
15648:
15550:
15515:
15446:
15346:
15195:
15163:
15101:
14528:
14317:
14257:
14057:
13942:
13783:
13758:
13613:
13355:
13305:
13245:
12906:
12319:
12030:
11988:
11959:
11806:
11760:
10952:
10895:
9737:
9732:
8774:
8756:
8728:
8402:
8392:
8134:
8129:
8057:
8052:
7994:
7989:
7943:
7917:
7853:
7792:
7787:
7704:
7664:
7532:
7268:
7261:
6644:
6527:"Russell Marker Creation of the Mexican Steroid Hormone Industry"
5539:(Seventh ed.). : Sinauer Associates; W.H. Freeman & Co.
3108:
3054:
2846:
2806:
2508:
2370:
2223:
2211:
2175:
2042:
1996:
1855:
proteins, a pathway which is hyperactive in a number of cancers.
1842:
1703:
1664:
1512:
1316:, with prominent members and examples of related functions, are:
921:
348:
166:
17824:
Meprednisone hydrogen succinate (methylprednisone hemisuccinate)
12236:
4361:
Proceedings of the Society for Experimental Biology and Medicine
3473:"sterol | Etymology, origin and meaning of sterol by etymonline"
3342:. London, GBR: Queen Mary University of London. p. 3S-1.4.
941:
19379:
16840:
16835:
16692:
15956:
15944:
15759:
15728:
15723:
15718:
15451:
15106:
14579:
14520:
14505:
14411:
11792:
11753:
11534:
8563:
8105:
7963:
7897:
7863:
7834:
7747:
7242:
4431:"11-Oxyandrogens in Adolescents With Polycystic Ovary Syndrome"
4332:
Makin HL, Trafford DJ (1972). "The chemistry of the steroids".
3062:
3008:
2834:
2194:(some testosterone may also be produced in the adrenal cortex).
2191:
2115:
2081:
1965:
1411:, which contributes to the development and maintenance of male
1391:
1244:
1159:
1012:
762:
747:
740:
594:
379:
375:
357:
344:
312:
245:
225:
221:
162:
154:
19675:
Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
16186:
3862:
3860:
1626:
59:
Polycyclic organic compound having sterane as a core structure
18056:
Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)
16916:
16790:
16672:
16642:
15861:
15743:
15572:
14111:
13793:
13703:
13634:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
13593:
12477:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
6558:
6415:
6297:
Annual Review of Plant Physiology and Plant Molecular Biology
6127:
3046:
2838:
2179:
1927:
1880:
1806:
1752:, "to cut") are a subclass of steroidal compounds resulting,
1737:
834:
645:
632:
158:
127:
88:
19670:
Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
5027:
3436:
3434:
18061:
Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
16936:
16717:
16627:
15996:
15751:
14544:
13857:
11902:
5979:
5567:
4135:
4133:
3857:
2877:
Isolation, structure determination, and methods of analysis
2842:
2215:
1775:
743:
206:
180:(plants). Lanosterol and cycloartenol are derived from the
6958:
6932:
6906:
6854:
6828:
6802:
6587:"Microbial conversion of tall oil sterols to C19 steroids"
5534:
4877:
4401:
3987:
paper or β (beta) if it lies above the plane of the paper.
3561:
3096:— Constitution of sterols and their connection to vitamins
3037:
Some steroidal hormones are economically obtained only by
1743:
18652:
16771:
14227:
12174:
7103:
A review of the history of steroid synthesis, especially
6880:
6070:
The Journal of Steroid Biochemistry and Molecular Biology
5501:
4607:
3431:
2920:
2854:
1174:
and cholesterol; the latter is a structural component of
353:
107:
rings (designated A, B, C, and D) arranged in a specific
18122:
Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)
13318:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
6585:
Conner AH, Nagaoka M, Rowe JW, Perlman D (August 1976).
6584:
6500:. Geneva Foundation for Medical Education and Research.
5595:
5572:(9 ed.). San Francisco: Freeman. pp. 105–114.
4130:
3721:. Springer Science & Business Media. pp. 624–.
12821:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
5030:
Drug Resistance in Bacteria, Fungi, Malaria, and Cancer
1725:-steroids for the androstanes (mostly androgens), and C
680:. These parent structures have specific names, such as
535:, a synthetic drug with effects similar to progesterone
406:
structure. When the two methyl groups and eight carbon
20722:
19680:
Hydroxyprogesterone heptanoate benzilic acid hydrazone
18851:
Prednicarbate (prednisolone ethylcarbonate propionate)
18191:
Non-corticosteroids with some glucocorticoid activity:
17411:
Prednicarbate (prednisolone ethylcarbonate propionate)
17038:
15087:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
13515:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
10577:(amino acid→pyruvate, acetyl CoA, or TCA intermediate)
6680:
6016:
1926:
The hundreds of steroids found in animals, fungi, and
20732:
10374:
6450:
5568:
Sadava D, Hillis DM, Heller HC, Berenbaum MR (2011).
4479:
4428:
4092:
19284:
17278:
Etiprednol dicloacetate (etiprednol dichloroacetate)
14601:
10994:
8632:
Terpene synthase enzymes (many), having in common a
5885:
4970:
4273:
3818:
1983:
In subsequent steps DMAPP and IPP conjugate to form
916:
Steroids are found in all domains of life including
228:
atoms, bonded in four fused rings: three six-member
18788:
Hydrocortamate (hydrocortisone diethylaminoacetate)
17955:
Amcinonide (triamcinolone acetate cyclopentanonide)
17778:
Icometasone enbutate (icometasone butyrate acetate)
17455:
Pregnenolone succinate (pregnenolone hemisuccinate)
17210:
Hydrocortamate (hydrocortisone diethylaminoacetate)
12949:
Normethandrone (methylestrenolone, normethisterone)
6713:
6564:. Dordrecht; New York: Springer. pp. 163–282.
6554:
6552:
5183:
4528:
4480:Turcu AF, Rege J, Auchus RJ, Rainey WE (May 2020).
4299:
3899:
3652:. London, GBR: Chapman and Hall. pp. xxx–lix.
3645:
3077:have been awarded for steroid research, including:
20457:Tooltip Selective progesterone receptor modulators
18665:
18362:Tooltip Selective glucocorticoid receptor agonists
18029:Fludroxycortide (flurandrenolone, flurandrenolide)
6998:Chemical History: Reviews of the Recent Literature
6451:Kliewer SA, Goodwin B, Willson TM (October 2002).
6025:"Diagram of the pathways of human steroidogenesis"
6022:
4358:
3593:
2795:deficiency in the 21-hydroxylase enzymatic pathway
165:. All steroids are manufactured in cells from the
18861:Prednisolamate (prednisolone diethylaminoacetate)
18110:Flupamesone (triamcinolone acetonide metembonate)
17421:Prednisolamate (prednisolone diethylaminoacetate)
13161:17α-Alkylated 5α-dihydrotestosterone derivatives:
7110:
6740:
5790:
5644:
5561:
5255:. Westport, CT: Greenwood Press. pp. 10–12.
5061:
5059:
5057:
5055:
5053:
5051:
5049:
3735:
2995:of steroids often begins from precursors such as
1863:Steroids and their metabolites often function as
1008:is conjectured – and the more-common pentacyclic
20867:
14691:
12406:
9461:11β-Hydroxyprogesterone (21-deoxycorticosterone)
6888:"The Nobel Prize in Physiology or Medicine 1950"
6775:
6640:
6638:
6549:
6336:International Journal of Pediatric Endocrinology
6197:
5528:
5502:Uemura E, Kita M, Arimoto H, Kitamura M (2009).
4812:: CS1 maint: bot: original URL status unknown (
4636:
4037:"3.5: Naming chiral centers- the R and S system"
3257:"Nomenclature of steroids, recommendations 1989"
3250:
3248:
3246:
3244:
2041:units, which are assembled and modified to form
1721:-steroids for the estranes (mostly estrogens), C
72:Steroids (Crouching Tiger Hidden Gabber Megamix)
20768:11-Deoxycortisol (17α,21-dihydroxyprogesterone)
18066:Procinonide (fluocinolone acetonide propionate)
17051:
13380:5α-Dihydro-17α-ethynyltestosterone derivatives:
6521:
6519:
6123:
6121:
6119:
5791:Dubey VS, Bhalla R, Luthra R (September 2003).
5751:
5749:
5591:
5589:
5269:
5161:Mind-altering and poisonous plants of the world
5136:Mind-altering and poisonous plants of the world
4921:
4794:. Archived from the original on 18 January 2017
4601:
4482:"11-Oxygenated androgens in health and disease"
4226:
4224:
4222:
4220:
4218:
4216:
4214:
4212:
3539:
3365:
3363:
3361:
2057:). Here, the isoprene units are joined to make
1223:, including most synthetic steroid drugs, with
560:In addition to the ring scissions (cleavages),
20141:11β-Methyl-19-nortestosterone dodecylcarbonate
17552:Ciclometasone (ciclomethasone, cyclomethasone)
16191:Tooltip Selective estrogen receptor modulators
15546:Furostilbestrol (diethylstilbestrol difuroate)
14907:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
12831:11β-Methyl-19-nortestosterone dodecylcarbonate
9758:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
7710:Iridoid glycosides (iridoids bound to a sugar)
6781:
6683:Ullmann's Encyclopedia of Industrial Chemistry
6676:
6674:
6672:
5846:
5844:
5537:Human physiology : an integrated approach
5305:
5046:
5021:
4826:
4739:
3953:
3646:Hill RA, Makin HL, Kirk DN, Murphy GM (1991).
2805:(DHT, a potent androgen) through among others
1934:(in animals and fungi; see examples above) or
1893:
1445:
1243:(which help maintain blood volume and control
889:needs attention from an expert in pharmacology
338:
252:at position three and a skeleton derived from
198:which was first described in gall stones from
19470:17α-Hydroxyprogesterone (hydroxyprogesterone)
19297:
19270:
19234:Mineralocorticoids and antimineralocorticoids
18929:17α-Hydroxyprogesterone (hydroxyprogesterone)
18638:
17795:Locicortolone dicibate (locicortone dicibate)
17073:Cortisol-like and related (16-unsubstituted):
17024:
14737:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
14677:
13598:Tooltip Selective androgen receptor modulator
13243:17α-Alkylated 19-nortestosterone derivatives:
12392:
10968:
10360:
9233:
8688:
7648:
7209:
7062:
6635:
6294:
5851:Schroepfer GJ (1981). "Sterol biosynthesis".
5226:"International Journal of Molecular Sciences"
4331:
3768:
3394:
3241:
3139:— In part, for the synthesis of cholesterol,
2305:
2298:
2248:
1633:, an example of a complex C-nor-D-homosteroid
1110:in place of ergosterol in its cell membrane.
931:
19460:16-Methylene-17α-hydroxyprogesterone acetate
14847:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
13649:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
6516:
6444:
6409:
6374:
6329:
6323:
6288:
6229:
6162:
6116:
6057:
5973:
5922:
5784:
5755:
5746:
5687:
5638:
5586:
5334:
5299:
5177:
5084:
4964:
4915:
4871:
4522:
4473:
4422:
4352:
4230:
4209:
3673:
3495:
3464:
3358:
2049:(a large class of lipids, which include the
1090:as an example, other major steroids include
91:-approved ring lettering and atom numbering.
18944:Canrenoate potassium (potassium canrenoate)
18783:Benzodrocortisone (hydrocortisone benzoate)
18709:11-Deoxycortisol (cortodoxone, cortexolone)
17338:Halopredone acetate (halopredone diacetate)
17205:Benzodrocortisone (hydrocortisone benzoate)
17115:11-Deoxycortisol (cortodoxone, cortexolone)
16722:Tooltip G protein-coupled estrogen receptor
15541:Fosfestrol (diethylstilbestrol diphosphate)
13400:17α-Ethynyl-19-nortestosterone derivatives:
7184:. Colorado State University. Archived from
7059:A concise history of the study of steroids.
6669:
6485:
6332:"Nonclassic congenital adrenal hyperplasia"
5879:
5841:
5495:
5450:
5158:
5133:
4571:
4178:
4061:
3998:
3587:
3388:
3049:steroids). For example, the pharmaceutical
3025:in the early days of the synthetic steroid
2824:
2178:and progesterone are made primarily in the
1790:reactions, and the latter is accomplished (
724:—a specific nomenclature distinct from the
240:attached to this four-ring core and by the
23:
20763:11-Deoxycortisone (21-hydroxyprogesterone)
19855:Gestonorone caproate (gestronol hexanoate)
19277:
19263:
18645:
18631:
17031:
17017:
15684:Triphenylmethylethylene (triphenylpropene)
15008:, many others; via estrogenic metabolites)
14932:17α-Epiestriol (16α-hydroxy-17α-estradiol)
14684:
14670:
13122:Methylclostebol (chloromethyltestosterone)
13017:5α-Dihydro-19-nortestosterone derivatives:
12399:
12385:
10975:
10961:
10367:
10353:
9753:17α-Epiestriol (16α-hydroxy-17α-estradiol)
9240:
9226:
8695:
8681:
7655:
7641:
7223:
7216:
7202:
6734:
6707:
6578:
5850:
5645:Grochowski LL, Xu H, White RH (May 2006).
5253:Steroids (Health and Medical Issues Today)
5244:
4062:Favre HA, Powell WH (2014). "P-13.8.1.1".
4055:
3686:Metabolism of Anabolic-Androgenic Steroids
2255:
2241:
1960:), making the pathway a common target for
1858:
1386:, which regulates cyclical changes in the
597:such as cholesterol and lanosterol have a
589:of groups attached to the rings and chain.
382:atoms in carbon-carbon bonds forming four
260:one of the rings. Cutting Ring B produces
24:
19447:17α-Substituted progesterone derivatives:
19355:17α-Methyl-11-deoxycorticosterone acetate
18254:Flugestone acetate (flurogestone acetate)
17545:Cortobenzolone (betamethasone salicylate)
14704:
13343:17α-Vinyl-19-nortestosterone derivatives:
12959:Oxabolone cipionate (oxabolone cypionate)
12575:DHEA (androstenolone, prasterone; 5-DHEA)
12419:
7088:
6618:
6468:
6357:
6347:
6145:
6063:
6040:
5956:
5946:
5729:
5711:
5670:
5613:
5519:
5429:
5419:
5395:
5369:
5201:
5152:
5127:
5004:
4947:
4854:
4844:
4767:
4757:
4505:
4456:
4446:
4256:
3789:
3706:
3638:
3621:
3611:
3546:(in French). Chez Crochard. p. 346.
3533:
3529:– via Deutsche Digitale Bibliothek.
2950:yields C-19 steroids, C-22 steroids, and
17985:Desonide (hydroxyprednisolone acetonide)
17940:Acrocinonide (triamcinolone acroleinide)
17498:Methasones and related (16-substituted):
13050:Chlorodehydromethylandrostenediol (CDMA)
7034:
6784:Journal of the American Chemical Society
6716:Journal of the American Chemical Society
6685:. Wiley-VCH Verlag GmbH & Co. KGaA.
6531:International Historic Chemical Landmark
6380:
5065:
4971:Siedenburg G, Jendrossek D (June 2011).
4572:Favre H, Powell W (2014). "Appendix 2".
4565:
4325:
3679:
3501:
3369:
2786:as substrates to produce IPP and DMAPP.
2109:
2007:
1897:
1875:. Steroids such as cholesterol decrease
1625:
1605:
1436:Additional classes of steroids include:
1146:(which include several plant hormones).
644:
619:
363:
352:
236:ring (the D ring). Steroids vary by the
78:
32:This is an accepted version of this page
19890:Oxogestone phenpropionate (xinogestone)
19850:Gestonorone acetate (gestronol acetate)
18731:16α,18-Dihydroxy-11-deoxycorticosterone
18602:Glucocorticoids and antiglucocorticoids
17950:Amcinafide (triamcinolone acetophenide)
14651:List of androgens and anabolic steroids
13037:17α-Alkylated testosterone derivatives:
9247:
7182:Pathophysiology of the Endocrine System
7063:Yoder RA, Johnston JN (December 2005).
6168:
5456:
5401:
4395:
4334:Clinics in Endocrinology and Metabolism
3992:
3305:Also available with the same authors at
2769:
2061:and folded into a set of rings to make
1744:Cleaved, contracted, and expanded rings
869:
14:
20868:
20727:Tooltip Membrane progesterone receptor
19480:Acetomepregenol (mepregenol diacetate)
18909:7α-Thiomethylspironolactone (SC-26519)
18899:6β-Hydroxy-7α-thiomethylspironolactone
17717:Fluocortin butyl (fluocortin butylate)
13055:Chlorodehydromethyltestosterone (CDMT)
12811:Testifenon (testiphenon, testiphenone)
12216:
12207:
12200:
12179:
12172:
12165:
12156:
12147:
12140:
12133:
12124:
12117:
12110:
12093:
12084:
12077:
12068:
12061:
12054:
12047:
12019:
12012:
12005:
11998:
11986:
11979:
11957:
11944:
11931:
11907:
11900:
11891:
11884:
11858:
11851:
11830:
11811:
11797:
11783:
11774:
11765:
11758:
11751:
11733:
11724:
11715:
11708:
11699:
11692:
11683:
11676:
11669:
11648:
11641:
11632:
11625:
11616:
11609:
11602:
11595:
11588:
11581:
11574:
11567:
11450:
11435:
11422:
11409:
11396:
11383:
11370:
11355:
11325:
11312:
11297:
11280:
11265:
11250:
11237:
11220:
11205:
11190:
11144:
11133:
11120:
11105:
11090:
11077:
11064:
11051:
11036:
11023:
11010:
9542:Adrenosterone (11-ketoandrostenedione)
6995:
6591:Applied and Environmental Microbiology
5340:
4977:Applied and Environmental Microbiology
4231:Miller WL, Auchus RJ (February 2011).
3769:Masiutin MM, Yadav MK (3 April 2023).
3346:from the original on 10 September 2017
3223:Steroidogenic acute regulatory protein
3129:— Structure and biological effects of
899:may be able to help recruit an expert.
20737:Tooltip Progestin and adipoQ receptor
19258:
18904:7α-Acetylthio-17α-hydroxyprogesterone
18626:
18607:Mineralocorticoid receptor modulators
18024:Fluclorolone acetonide (flucloronide)
17945:Amcinafal (triamcinolone pentanonide)
17345:Isoflupredone (9α-fluoroprednisolone)
17012:
14665:
13336:Norvinisterone (vinylnortestosterone)
12870:Bolmantalate (nandrolone adamantoate)
12865:Bolandione (19-nor-4-androstenedione)
12580:DHEA enanthate (prasterone enanthate)
12380:
12368:
12367:
12188:
12035:
12028:
11922:
11871:
11844:
11818:
11742:
11662:
11655:
11555:
11548:
11539:
11522:
11513:
11495:
11482:
11469:
11340:
11175:
11160:
10956:
10348:
9748:16β-Epiestriol (16β-hydroxyestradiol)
9221:
8676:
7636:
7197:
7175:
7148:
7022:from the original on 12 February 2020
6743:Microbial Transformations of Steroids
6537:from the original on 12 February 2020
6504:from the original on 17 February 2015
6211:from the original on 10 February 2024
5928:
5250:
5232:from the original on 12 February 2024
4721:from the original on 12 February 2024
4703:
4691:from the original on 12 February 2024
4596:oxy* –O– P-15.3.1.2.1.1; P-63.2.2.1.1
3937:from the original on 19 February 2024
3764:
3762:
3760:
3758:
3756:
3754:
3752:
3750:
3741:
3712:
3575:from the original on 22 November 2023
3294:from the original on 30 November 2012
2966:). The addition and modification of
2934:
2003:
1557:
1364:through water and electrolyte balance
1178:that helps determine the fluidity of
1154:Animal steroids include compounds of
853:with an oxygen atom connected to two
688:, etc. The derivatives carry various
194:Steroids are named after the steroid
14606:Tooltip Sex hormone-binding globulin
13353:17α-Ethynyltestosterone derivatives:
12632:Polytestosterone phloretin phosphate
11400:
10477:Electron acceptors other than oxygen
6972:from the original on 20 October 2012
6946:from the original on 22 October 2012
6920:from the original on 6 November 2012
6894:from the original on 19 October 2012
6868:from the original on 20 October 2012
6842:from the original on 17 October 2012
6816:from the original on 20 October 2012
6741:Capek M, Oldrich H, Alois C (1966).
6276:from the original on 29 January 2024
5935:Drug Design, Development and Therapy
5438:from the original on 1 February 2013
5090:
5066:Kavanagh K, ed. (8 September 2017).
4531:Molecular and Cellular Endocrinology
4172:
4043:from the original on 1 November 2023
3999:Favre HA, Powell WH (2014). "P-91".
2053:and form the largest class of plant
1561:
1274:
935:
873:
862:appropriate to use this convention.
716:The letters α and β denote absolute
663:
413:Examples of steroid structures are:
311:in the middle (grey, black) and the
153:. Hundreds of steroids are found in
13276:Methylhydroxynandrolone (MOHN, MHN)
12981:Trenbolone hexahydrobenzylcarbonate
12641:5α-Dihydrotestosterone derivatives:
12509:Androstenedione (4-androstenedione)
9918:Estradiol 3-glucuronide 17β-sulfate
7018:. American Chemical Society. 1999.
6966:"The Nobel Prize in Chemistry 1975"
6940:"The Nobel Prize in Chemistry 1969"
6914:"The Nobel Prize in Chemistry 1965"
6862:"The Nobel Prize in Chemistry 1939"
6836:"The Nobel Prize in Chemistry 1928"
6810:"The Nobel Prize in Chemistry 1927"
6649:in the presence of cyclodextrins".
6491:
6223:
5865:10.1146/annurev.bi.50.070181.003101
5184:Ericson-Neilsen W, Kaye AD (2014).
4684:Biological significance of steroids
4313:from the original on 7 October 2023
4287:from the original on 6 October 2023
4179:Favre HA, Powell WH (2014). "P-3".
3521:from the original on 4 October 2023
3397:The New England Journal of Medicine
2829:Steroids are primarily oxidized by
1092:ergosta‐5,7,22,24(28)‐tetraen‐3β‐ol
1039:, utilize this information to kill
56:
19926:6,6-Difluoronorethisterone acetate
19239:Glucocorticoid receptor modulators
18670:Tooltip Mineralocorticoid receptor
13333:17α-Vinyltestosterone derivatives:
13095:Methandriol (methylandrostenediol)
10982:
8634:terpene synthase N terminal domain
6104:from the original on 26 April 2021
4657:10.1111/j.1432-1033.1989.tb15228.x
4630:10.1016/j.combustflame.2013.02.024
4576:. The Royal Society of Chemistry.
4183:. The Royal Society of Chemistry.
4154:10.1111/j.1432-1033.1989.tb15228.x
4113:10.1111/j.1432-1033.1989.tb15228.x
4066:. The Royal Society of Chemistry.
4003:. The Royal Society of Chemistry.
3974:10.1111/j.1432-1033.1989.tb15228.x
3923:10.1111/j.1432-1033.1989.tb15228.x
3881:10.1111/j.1432-1033.1989.tb15228.x
3839:10.1111/j.1432-1033.1989.tb15228.x
3747:
3483:from the original on 19 March 2023
3470:
3322:10.1111/j.1432-1033.1989.tb15228.x
3068:
3032:
2167:, aldosterone are produced in the
2103:
1922:(the first steroid in the pathway)
1526:As well as the following class of
1182:and is a principal constituent of
1070:Ergosterol is responsible for the
66:. For the scientific journal, see
57:
20892:
20834:Progestogens and antiprogestogens
20241:Methoxydienone (methoxygonadiene)
19635:Fluoromedroxyprogesterone acetate
18741:18-Hydroxy-11-deoxycorticosterone
18259:Fluoromedroxyprogesterone acetate
16083:taleranol (teranol, β-zearalanol)
14998:metandienone (methandrostenolone)
13373:Ethisterone (ethynyltestosterone)
13090:Metandienone (methandrostenolone)
12920:Methoxydienone (methoxygonadiene)
12531:Boldione (1,4-androstadienedione)
12482:Androstenediol (5-androstenediol)
12447:4-Dehydroepiandrosterone (4-DHEA)
9466:18-Hydroxy-11-deoxycorticosterone
9316:11β,17α,21-Trihydroxypregnenolone
7149:Greep RO, ed. (22 October 2013).
6023:Häggström M, Richfield D (2014).
5383:from the original on 4 March 2016
1993:squalene/phytoene synthase family
1733:" is also important in medicine.
1118:Plant steroids include steroidal
730:Cahn–Ingold–Prelog priority rules
20201:Dimethandrolone dodecylcarbonate
20134:; Anabolic–androgenic steroids:
19390:Progesterone 3-acetyl enol ether
18954:Canrenone (canrenoate y-lactone)
18919:7α-Thiospironolactone (SC-24813)
18690:11-Dehydrocorticosterone acetate
17870:Prednylidene diethylaminoacetate
17853:Paramethasone disodium phosphate
17622:Desoximetasone (desoxymethasone)
17477:Butixocort (tixocortol butyrate)
17096:11-Dehydrocorticosterone acetate
16993:Progesterone receptor modulators
16747:Afimoxifene (4-hydroxytamoxifen)
15629:Prinaberel (ERB-041, WAY-202041)
14646:Progesterone receptor modulators
13137:Methyltestosterone 3-hexyl ether
13100:Methandriol bisenanthoyl acetate
13060:Chloromethylandrostenediol (CMA)
12895:Dimethandrolone dodecylcarbonate
12654:1-Androsterone (1-andro, 1-DHEA)
12345:
12329:
12313:
12301:
12289:
12277:
12265:
12253:
12235:
11002:
7145:Adrenal steroidogenesis pathway.
6395:10.1016/j.pharmthera.2006.05.014
6236:Sex Hormones, Exercise and Women
5287:from the original on 12 May 2023
4893:10.1046/j.1365-2958.2003.03309.x
4435:Journal of the Endocrine Society
3962:European Journal of Biochemistry
3911:European Journal of Biochemistry
3805:
3310:European Journal of Biochemistry
2986:
1566:
1279:
1231:(which regulate many aspects of
940:
878:
802:for refer to Δ-steroids, while "
601:attached at position C-3, while
540:
525:
510:
487:
468:
441:
419:
290:
278:
19905:Segesterone acetate (nestorone)
19797:19-Norprogesterone derivatives:
19450:6α-Methyl-17α-bromoprogesterone
19034:Oxprenoate potassium (RU-28318)
18812:Fludrocortisone (fludrocortone)
18324:Segesterone acetate (nestorone)
17937:Cyclic ketals (16,17-cyclized):
17814:Meprednisone (methylprednisone)
17736:Fluprednidene (fluprednylidene)
17285:Fludrocortisone (fludrocortone)
17086:9α-Fluorocortisone (alfluorone)
17056:Tooltip Glucocorticoid receptor
16690:Coregulator-binding modulators:
14957:17β-Methyl-17α-dihydroequilenin
12818:19-Nortestosterone derivatives:
10498:Substrate-level phosphorylation
9667:Dihydrotestosterone glucuronide
6988:
6651:Enzyme and Microbial Technology
6383:Pharmacology & Therapeutics
6309:10.1146/annurev.arplant.50.1.47
6260:
5663:10.1128/JB.188.9.3192-3198.2006
5218:
5068:Fungi: Biology and Applications
4820:
4784:
4733:
4029:
3771:"Alternative androgen pathways"
3719:Comparative Animal Biochemistry
3540:Arago F, Gay-Lussac JL (1816).
3061:, a petrochemical derived from
2819:3α-Hydroxysteroid dehydrogenase
2293:Reference range (serum levels)
2104:
1794:) or (more frequently) through
1552:
1054:Ergosterol is analogous to the
631:animal sterol. This structural
333:
20058:Norethisterone (norethindrone)
19835:Fluoro furanyl norprogesterone
19455:15β-Hydroxycyproterone acetate
19402:Retroprogesterone derivatives:
18714:Cortifen (cortiphen, kortifen)
18194:15β-Hydroxycyproterone acetate
18115:Triamcinolone acetonide esters
17523:Beclometasone (beclomethasone)
17120:Cortifen (cortiphen, kortifen)
17076:3α,5α-Tetrahydrocorticosterone
15521:Erteberel (SERBA-1, LY-500307)
13833:15β-Hydroxycyproterone acetate
13724:OPK-88004 (LY-2452473, TT-701)
9343:3α,5α-Tetrahydrocorticosterone
5070:. John Wiley & Sons, Inc.
4922:Desmond E, Gribaldo S (2009).
4827:Hoshino Y, Gaucher EA (2021).
4740:Hoshino Y, Gaucher EA (2021).
3340:"The Nomenclature of Steroids"
2791:congenital adrenal hyperplasia
1450:Tooltip dehydroepiandrosterone
1270:
827:5α-pregnane-3α,17α-diol-20-one
70:. For the Death Grips EP, see
13:
1:
20829:Receptor/signaling modulators
20136:11β-Methyl-19-nortestosterone
19800:17α-Methyl-19-norprogesterone
19302:Tooltip Progesterone receptor
19229:Receptor/signaling modulators
18914:7α-Thioprogesterone (SC-8365)
18597:Receptor/signaling modulators
18514:Pregnenolone 16α-carbonitrile
18336:Nonsteroidal glucocorticoids:
17501:16α-Methyl-11-oxoprednisolone
16978:Receptor/signaling modulators
14942:17α-Ethynyl-3β-androstanediol
14937:17α-Ethynyl-3α-androstanediol
14631:Receptor/signaling modulators
13388:17α-Ethynyl-3β-androstanediol
13383:17α-Ethynyl-3α-androstanediol
12826:11β-Methyl-19-nortestosterone
10901:Reverse cholesterol transport
9622:3α-Androstanediol glucuronide
7113:Nature Reviews. Endocrinology
7037:Steroid Chemistry at a Glance
6611:10.1128/AEM.32.2.310-311.1976
6533:. American Chemical Society.
6230:Davis HC, Hackney AC (2017).
6064:Hanukoglu I (December 1992).
5994:10.1158/1078-0432.CCR-06-0843
5853:Annual Review of Biochemistry
5461:. In Corey EJ, Li JJ (eds.).
5320:10.1016/S0010-7824(99)00101-8
5113:10.1016/S0031-9422(03)00300-5
4486:Nature Reviews. Endocrinology
4346:10.1016/S0300-595X(72)80024-0
3968:(3): 429–458. December 1989.
3917:(3): 429–458. December 1989.
3713:Urich K (16 September 1994).
3569:"R-2.4.1 Fusion nomenclature"
3372:Steroid Chemistry at a Glance
3316:(3): 429–458. December 1989.
3234:
3213:Reverse cholesterol transport
3193:List of steroid abbreviations
2981:
2861:at various ring positions or
1471:neuromuscular blocking agents
1413:secondary sex characteristics
1190:). Steroid hormones include:
1162:origin, the latter including
297:Ball-and-stick representation
248:are forms of steroids with a
20881:Polycyclic organic compounds
20844:Estrogen receptor modulators
20839:Androgen receptor modulators
20226:Ethylestrenol (ethylnandrol)
20156:19-Nordehydroepiandrosterone
20038:Lynestrenol phenylpropionate
19931:17α-Allyl-19-nortestosterone
19830:Fluoro ethyl norprogesterone
19805:18-Methylsegesterone acetate
19705:Medroxyprogesterone caproate
19335:9α-Bromo-11-ketoprogesterone
18994:Hydroxyprogesterone caproate
17627:Dexamethasone (dexametasone)
17535:Betamethasone (betametasone)
16988:Androgen receptor modulators
15292:Lynestrenol phenylpropionate
14641:Estrogen receptor modulators
14088:Trimethyltrienolone (R-2956)
13460:Lynestrenol phenylpropionate
12848:19-Nordehydroepiandrosterone
10553:(protein→peptide→amino acid)
9311:17α,21-Dihydroxypregnenolone
8845:Geranylgeranyl pyrophosphate
8111:Geranylgeranyl pyrophosphate
7176:Bowen RA (20 October 2001).
6663:10.1016/0141-0229(89)90133-6
6494:"Steroid Hormone Metabolism"
6330:Witchel SF, Azziz R (2010).
6082:10.1016/0960-0760(92)90307-5
5570:Life: The Science of Biology
5421:10.3998/ark.5550190.0008.517
4928:Genome Biology and Evolution
4416:10.1016/0039-128X(64)90003-0
3680:Rogozkin VA (14 June 1991).
3011:, a company involved in the
2774:In plants and bacteria, the
2088:), which are used to reduce
1710:
1707:
1702:
1697:
1694:
1689:
1684:
1681:
1676:
1671:
1668:
1663:
1658:
1655:
1650:
1645:
1642:
1639:
1023:Fungal steroids include the
839:5α-pregnan-17α-ol-3,20-dione
768:androst-4-ene-3,11,17-trione
285:Space-filling representation
7:
20264:nandrolone phenylpropionate
20206:Dimethandrolone undecanoate
19700:Medroxyprogesterone acetate
19665:Hydroxyprogesterone acetate
19545:Chlormethenmadinone acetate
19054:Prorenoic acid (prorenoate)
19029:Oxprenoic acid (oxprenoate)
19019:Mexrenoic acid (mexrenoate)
18949:Canrenoic acid (canrenoate)
18570:Antisense oligonucleotides:
18279:Medroxyprogesterone acetate
17990:Desonide disodium phosphate
17790:Locicortolone (locicortone)
16983:Estrogens and antiestrogens
16633:Oxabicycloheptene sulfonate
16320:Etacstil (GW-5638, DPC-974)
15496:Doisynoestrol (fenocycline)
15240:Ethinylestradiol 3-benzoate
14752:3β,5α-Dihydrolevonorgestrel
14747:3α,5α-Dihydrolevonorgestrel
14636:Androgens and antiandrogens
14407:Ralaniten acetate (EPI-506)
13823:7α-Thiomethylspironolactone
13538:Medroxyprogesterone acetate
12900:Dimethandrolone undecanoate
12711:Dihydromethylandrostenediol
12502:Androstenediol dipropionate
9687:Etiocholanolone glucuronide
9672:Dihydrotestosterone sulfate
8824:Dimethylallyl pyrophosphate
8661:Dimethylallyl pyrophosphate
6244:10.1007/978-3-319-44558-8_1
6147:10.1016/j.jsbmb.2023.106436
5159:Wink M, van Wyk BE (2008).
5134:Wink M, Van Wyk BE (2008).
3644:Also available in print at
3477:Online Etymology Dictionary
3175:
3094:Adolf Otto Reinhold Windaus
2873:and excreted in the urine.
2863:oxidized at the 17 position
2232:or from peripheral sources.
2090:elevated cholesterol levels
1952:Steroid biosynthesis is an
1908:dimethylallyl pyrophosphate
1894:Biosynthesis and metabolism
1491:(mainly exogenous) such as
1482:(mainly synthetic) such as
1473:(mainly synthetic) such as
891:. The specific problem is:
759:4-androstene-3,11,17-trione
676:structure that serves as a
339:Rings and functional groups
10:
20897:
19921:6,6-Difluoronorethisterone
19179:Miricorilant (CORT-118335)
18654:Mineralocorticoid receptor
18519:Relacorilant (CORT-125134)
18489:Miricorilant (CORT-118335)
17690:Flumetasone (flumethasone)
17605:Cormetasone (cormethasone)
17511:Alclometasone dipropionate
16700:Noncompetitive inhibitors:
16325:Ethamoxytriphetol (MER-25)
15486:Dimestrol (dianisylhexene)
15245:Ethinylestradiol sulfonate
12726:Dihydrotestosterone esters
12679:11-Ketodihydrotestosterone
12492:Androstenediol 17β-acetate
12472:11β-Hydroxyandrostenedione
12457:4,17α-Dimethyltestosterone
10938:Phospagen system (ATP-PCr)
10408:Primary nutritional groups
9592:16α-Hydroxyandrostenedione
9537:11β-Hydroxyandrostenedione
9522:11-Ketodihydrotestosterone
6183:10.1016/j.ceca.2006.04.020
6134:J Steroid Biochem Mol Biol
4973:"Squalene-hopene cyclases"
3688:. CRC Press. pp. 1–.
2784:glyceraldehyde 3-phosphate
2450:
2121:
2015:
1788:ring expansion-contraction
1489:Steroidogenesis inhibitors
1004:) – where its origin from
932:Eukaryotic and Prokaryotic
841:", where the last "e" of "
617:
342:
61:
20821:
20801:
20745:
20720:
20602:
20447:
20326:Spirolactone derivatives:
20196:Dimethandrolone buciclate
19917:Testosterone derivatives:
19685:Mecigestone (pentarane B)
19515:Bromethenmadinone acetate
19405:20α-Dihydrodydrogesterone
19317:Progesterone derivatives:
19309:
19295:
19221:
18888:
18677:
18663:
18589:
18562:
18449:Exicorilant (CORT-125281)
18389:
18352:
17680:Doxibetasol (doxybetasol)
17377:Methylprednisolone esters
17362:Mazipredone (depersolone)
17142:Δ-Prednisolone 21-acetate
17063:
17049:
16970:
16945:
16909:
16742:7β-Hydroxyepiandrosterone
16729:
16715:
16528:
16300:Desmethylchlorotrianisene
16181:
15479:Diethylstilbestrol esters
15432:Bisdehydrodoisynolic acid
14852:11β-Chloromethylestradiol
14827:7β-Hydroxyepiandrosterone
14716:
14709:Tooltip Estrogen receptor
14702:
14623:
14513:
14504:
13802:
13591:
13530:Progesterone derivatives:
13321:5α-Dihydronorethandrolone
12890:Dimethandrolone buciclate
12720:androstanolone, stanolone
12716:Dihydrotestosterone (DHT)
12674:7β-Hydroxyepiandrosterone
12563:Cloxotestosterone acetate
12487:Androstenediol 3β-acetate
12439:Testosterone derivatives:
12431:
12424:Tooltip Androgen receptor
12417:
12374:
10991:
10913:
10873:
10845:
10826:
10800:
10772:Anoxygenic photosynthesis
10762:
10755:
10726:
10694:Pentose phosphate pathway
10689:
10672:
10655:
10648:
10628:
10589:
10560:
10536:
10527:
10484:
10468:
10449:Oxidative phosphorylation
10427:
10416:
10390:
10280:
10209:7β-Hydroxyepiandrosterone
10204:7α-Hydroxyepiandrosterone
10052:
9970:
9710:
9532:7β-Hydroxyepiandrosterone
9512:
9503:
9431:
9333:
9324:
9258:
9167:
9107:
9100:
9056:
8941:
8889:
8880:
8853:
8832:
8819:Isopentenyl pyrophosphate
8814:5-Diphosphomevalonic acid
8793:
8765:
8726:
8717:
8655:Isopentenyl pyrophosphate
8647:
8625:
8609:Norisoprenoids (modified)
8608:
8581:
8533:
8480:
8465:
8448:
8385:
8312:
8302:
8285:
8224:
8198:
8168:
8143:
8122:
8098:
8088:
8027:
7982:
7931:
7885:
7876:
7827:
7801:
7780:
7761:
7723:
7680:
7614:
7593:
7565:
7546:
7522:
7503:
7430:
7411:
7304:
7251:
7232:
6751:10.1007/978-94-011-7603-3
5929:Kones R (December 2010).
5700:Frontiers in Pharmacology
5471:10.1007/978-3-642-34065-9
5431:2027/spo.5550190.0008.517
4543:10.1016/j.mce.2021.111189
4498:10.1038/s41574-020-0336-x
4373:10.3181/00379727-85-20905
3613:10.3390/molecules28020771
3442:"Lanosterol biosynthesis"
3218:Steroidogenesis inhibitor
3203:Membrane steroid receptor
3021:to produce the sapogenin
2727:
2682:
2637:
2572:
2507:
2312:
2292:
2287:
2282:
2277:
2272:
2269:
2266:
2160:of the respective tissue.
2028:dimethylallyl diphosphate
1974:dimethylallyl diphosphate
1904:isopentenyl pyrophosphate
1511:Toxins such as steroidal
1497:Membrane sterols such as
1149:
1018:
821:The suffix -ol denotes a
20479:5α-Dihydronorethisterone
20474:5α-Dihydrolevonorgestrel
20384:3,8-Dihydrodiligustilide
20151:19-Nor-5-androstenedione
20071:norethisterone enanthate
20027:levonorgestrel butanoate
17918:Ulobetasol (halobetasol)
17159:Chloroprednisone acetate
17081:5α-Dihydrocorticosterone
16806:Fulvestrant (ICI-182780)
16623:Methylpiperidinopyrazole
16576:Fulvestrant (ICI-182780)
16059:Resorcylic acid lactones
15282:Hydroxyestrone diacetate
15218:Etamestrol (eptamestrol)
14336:-Butylbenzenesulfonamide
13523:5α-Dihydronorethisterone
13518:5α-Dihydrolevonorgestrel
13480:norethisterone enanthate
13449:levonorgestrel butanoate
13326:5α-Dihydronormethandrone
13179:Mebolazine (dimethazine)
13169:Desoxymethyltestosterone
13110:Methandriol dipropionate
12907:LS-1727 (nandrolone 17β-
12843:19-Nor-5-androstenedione
12701:Dihydroethyltestosterone
12497:Androstenediol diacetate
10792:Entner-Doudoroff pathway
10454:electron transport chain
10441:Pyruvate decarboxylation
10094:5α-Dihydrocorticosterone
10035:Pregnanediol glucuronide
9697:Testosterone glucuronide
9657:Androsterone glucuronide
9602:16α-Hydroxy-DHEA sulfate
9471:18-Hydroxycorticosterone
9423:3α,5α-Tetrahydrocortisol
9348:5α-Dihydrocorticosterone
8648:Activated isoprene forms
8449:Sesquarterpenes/oids (7)
7698:Monocyclic (single ring)
6968:. The Nobel Foundation.
6942:. The Nobel Foundation.
6916:. The Nobel Foundation.
6890:. The Nobel Foundation.
6864:. The Nobel Foundation.
6838:. The Nobel Foundation.
6812:. The Nobel Foundation.
6691:10.1002/14356007.a13_089
5988:(20 Pt 2): 6222s–6230s.
5982:Clinical Cancer Research
5713:10.3389/fphar.2018.01027
5521:10.1351/PAC-CON-08-08-12
3336:Also available online at
2845:. The expression of the
2825:Catabolism and excretion
2749:metabolic clearance rate
1619:), an example of a 9,10-
1339:whose functions include
1265:
1113:
1087:Saccharomyces cerevisiae
897:WikiProject Pharmacology
786:The abbreviations like "
39:latest accepted revision
20773:17α-Hydroxyprogesterone
20509:Metapristone (RU-42633)
20290:Trenbolone (trienolone)
20146:19-Nor-5-androstenediol
19946:Chloroethynylnorgestrel
19860:Gestronol (gestonorone)
19790:Triamcinolone acetonide
19745:Methenmadinone caproate
19620:Fluorometholone acetate
19365:20β-Dihydroprogesterone
19360:20α-Dihydroprogesterone
19350:16α-Hydroxyprogesterone
19244:List of corticosteroids
18939:18,19-Dinorprogesterone
18924:16α-Hydroxyprogesterone
18817:Fludrocortisone acetate
18766:Corticosterone benzoate
18726:11β-Hydroxyprogesterone
18612:List of corticosteroids
18474:Metapristone (RU-42633)
18199:17α-Hydroxyprogesterone
18105:Triamcinolone acetonide
17911:Triamcinolone diacetate
17858:Paramethasone phosphate
17661:Diflucortolone valerate
17656:Diflucortolone pivalate
17302:Fluorometholone acetate
17290:Fludrocortisone acetate
17188:Corticosterone benzoate
17040:Glucocorticoid receptor
16117:Synthetic xenoestrogens
15674:Triphenylchloroethylene
15609:Methestrol dipropionate
15137:Polyestradiol phosphate
14467:Topilutamide (fluridil)
13828:11α-Hydroxyprogesterone
12838:19-Nor-5-androstenediol
12738:Drostanolone propionate
12260:carbohydrate metabolism
10886:Sphingolipid metabolism
10787:DeLey-Doudoroff pathway
10635:carbohydrate catabolism
10630:Carbohydrate metabolism
10616:Purine nucleotide cycle
10329:11β-Hydroxyprogesterone
10324:11α-Hydroxyprogesterone
10000:20β-Dihydroprogesterone
9995:20α-Dihydroprogesterone
9990:17α-Hydroxyprogesterone
9985:16α-Hydroxyprogesterone
9913:Estradiol 3-glucuronide
9398:17α-Hydroxyprogesterone
9393:17α-Hydroxypregnenolone
9301:17α-Hydroxypregnenolone
9296:11β-Hydroxypregnenolone
9033:Cholesta-7,24-dien-3-ol
8984:4alpha-Methylzymosterol
8863:Prephytoene diphosphate
8711:metabolic intermediates
8271:Secodehydroabietic acid
7125:10.1038/nrendo.2013.239
7000:. Cambridge: RSC Publ.
6418:Molecular Pharmaceutics
6205:"Reproductive Hormones"
6029:WikiJournal of Medicine
5758:Natural Product Reports
5651:Journal of Bacteriology
5343:Natural Product Reports
4846:10.1073/pnas.2101276118
4792:"Steroids distribution"
4759:10.1073/pnas.2101276118
4742:"Steroids distribution"
3778:WikiJournal of Medicine
3277:10.1351/pac198961101783
3027:pharmaceutical industry
2960:adrenocortical hormones
2917:Structure determination
2831:cytochrome P450 oxidase
2799:17α-Hydroxyprogesterone
2032:isopentenyl diphosphate
1991:, which belongs to the
1978:isopentenyl diphosphate
1972:as building blocks for
1859:Biological significance
1646:Number of carbon atoms
1480:Steroidal antiandrogens
707:17α-hydroxyprogesterone
653:, a common steroid core
388:three-dimensional shape
126:. Examples include the
109:molecular configuration
20758:5β-Dihydroprogesterone
20753:5α-Dihydroprogesterone
20359:SC-5233 (spirolactone)
20166:Bolandiol dipropionate
20067:norethisterone acetate
19740:Methenmadinone acetate
19535:Chlormadinone caproate
19495:Algestone acetophenide
19475:17α-Methylprogesterone
19410:20α-Dihydrotrengestone
19345:11-Deoxycorticosterone
19340:11-Dehydroprogesterone
19325:5α-Dihydroprogesterone
19320:3β-Dihydroprogesterone
19074:SC-5233 (spirolactone)
18761:Corticosterone acetate
18736:17α-Hydroxyaldosterone
18504:ORG-34517 (SCH-900636)
18404:17α-Methylprogesterone
18051:Fluocinolone acetonide
17807:Meclorisone dibutyrate
17756:Fluticasone propionate
17598:Cloticasone propionate
17326:Fluprednisolone esters
17256:Dichlorisone diacetate
17183:Corticosterone acetate
16210:4'-Hydroxynorendoxifen
16205:2-Phenylbenzothiophene
16079:zeranol (α-zearalanol)
15782:phlorizin (phloridzin)
15669:Triphenylbromoethylene
15568:ICI-85966 (Stilbostat)
15149:Estramustine phosphate
15022:Bolandiol dipropionate
14352:-Desmethylenzalutamide
14058:SC-5233 (spirolactone)
13476:norethisterone acetate
13115:Methandriol propionate
12986:Trenbolone undecanoate
12858:Bolandiol dipropionate
12706:Dihydrofluoxymesterone
12669:5α-Androst-2-en-17-one
12524:Boldenone undecylenate
10855:Fatty acid degradation
10575:Amino acid degradation
10129:11-Deoxycorticosterone
10104:5β-Dihydroprogesterone
10099:5α-Dihydroprogesterone
10089:3β-Dihydroprogesterone
10084:3α-Dihydroprogesterone
10010:11-Deoxycorticosterone
10005:5α-Dihydroprogesterone
9652:Androstenediol sulfate
9632:5β-Dihydrotestosterone
9476:18-Hydroxyprogesterone
9456:11-Deoxycorticosterone
9353:11-Deoxycorticosterone
9306:21-Hydroxypregnenolone
8952:Farnesyl pyrophosphate
8882:Non-mevalonate pathway
8066:Farnesyl pyrophosphate
5800:Journal of Biosciences
5457:Gao G, Chen C (2012).
4881:Molecular Microbiology
4829:"Species distribution"
4448:10.1210/jendso/bvac037
3715:"Sterols and Steroids"
3649:Dictionary of Steroids
3115:Physiology or Medicine
3013:Mexican barbasco trade
2853:by the steroid sensor
2797:leads to an excess of
2776:non-mevalonate pathway
2220:central nervous system
2186:during pregnancy, and
2119:
2013:
1923:
1634:
1623:
1530:(open-ring steroids):
1081:Pneumocystis jirovecii
951:is missing information
781:5β-dihydrotestosterone
777:5α-dihydrotestosterone
654:
640:
372:
361:
92:
83:Structure of 24-ethyl-
20514:Mifepristone (RU-486)
20063:Norethisterone esters
20023:Levonorgestrel esters
19971:Ethinylandrostenediol
19775:Pentagestrone acetate
19660:Hydromadinone acetate
19530:Chlormadinone acetate
19465:17α-Bromoprogesterone
19330:6α-Methylprogesterone
19286:Progesterone receptor
18793:Hydrocortisone esters
18484:Mifepristone (RU-486)
18209:Chlormadinone acetate
18204:Bromoketoprogesterone
18162:Nicocortonide acetate
18093:Rofleponide palmitate
18012:Drocinonide phosphate
17980:Descinolone acetonide
17975:Deflazacort (azacort)
17923:Ulobetasol propionate
17887:Ticabesone propionate
17848:Paramethasone acetate
17741:Fluprednidene acetate
17644:Diflorasone diacetate
17562:Clobetasol propionate
17482:Butixocort propionate
17350:Isoflupredone acetate
17268:Endrisone (endrysone)
17215:Hydrocortisone esters
16390:Miproxifene phosphate
16215:27-Hydroxycholesterol
15679:Triphenyliodoethylene
15223:Ethinylandrostenediol
15186:Estrogenic substances
15174:Polyestriol phosphate
15042:Cloxestradiol acetate
14344:-Desmethylapalutamide
13873:Chlormadinone acetate
13818:7α-Thiospironolactone
13689:LGD-2941 (LGD-122941)
13679:LG121071 (LGD-121071)
13553:3-Keto-5α-abiraterone
13533:6α-Methylprogesterone
13472:Norethisterone esters
13445:Levonorgestrel esters
13361:Ethinylandrostenediol
13211:Methyl-1-testosterone
13131:+esterified estrogens
13105:Methandriol diacetate
12770:Mesterolone cipionate
12452:4-Hydroxytestosterone
12308:amino acid metabolism
10891:Eicosanoid metabolism
10847:Fatty acid metabolism
10611:Pyrimidine metabolism
10470:Anaerobic respiration
10319:7α-Hydroxycholesterol
10299:Calcidiol/Calcifediol
9928:Estradiol 17β-sulfate
9908:Estradiol glucuronide
9828:27-Hydroxycholesterol
9441:5α-Dihydroaldosterone
9286:-Dihydroxycholesterol
9085:-Dihydroxycholesterol
8979:14-demethyllanosterol
8840:Geranyl pyrophosphate
8809:Phosphomevalonic acid
8785:β-Hydroxybutyric acid
8268:Sandaracopimaric acid
7913:Geranyl pyrophosphate
7045:10.1002/9780470973639
6042:10.15347/wjm/2014.005
4582:10.1039/9781849733069
4189:10.1039/9781849733069
4072:10.1039/9781849733069
4009:10.1039/9781849733069
3791:10.15347/WJM/2023.003
3137:Robert Burns Woodward
3119:Edward Calvin Kendall
3087:Heinrich Otto Wieland
2113:
2037:DMAPP and IPP donate
2011:
1912:geranyl pyrophosphate
1901:
1629:
1609:
1312:The major classes of
1130:(specially the genus
1108:5,6‐dihydroergosterol
955:oxidosqualene cyclase
818:refer to Δ-steroids.
648:
623:
429:, the principal male
367:
356:
216:The steroid nucleus (
82:
20849:List of progestogens
20349:Potassium canrenoate
20303:trenbolone enanthate
20285:Tetrahydrogestrinone
20260:nandrolone decanoate
20236:Metribolone (R-1881)
20117:Quingestanol acetate
20048:Metynodiol diacetate
19730:Melengestrol acetate
19630:Flumedroxone acetate
19575:Clomegestone acetate
19049:Prorenoate potassium
19014:Mexrenoate potassium
18702:Desoxycortone esters
18329:Tetrahydrogestrinone
18169:Nivacortol (nivazol)
17819:Meprednisone acetate
17729:Fluocortolone esters
17700:Flumetasone pivalate
17632:Dexamethasone esters
17574:Clobetasone butyrate
17540:Betamethasone esters
17528:Beclometasone esters
17450:Pregnenolone acetate
17389:Prebediolone acetate
17251:Dichlorisone acetate
17239:Deprodone propionate
17108:Desoxycortone esters
15704:WAY-204688 (SIM-688)
15516:ERB-196 (WAY-202196)
15467:Dienestrol diacetate
15206:Estrone methyl ether
15112:Esterified estrogens
15054:Conjugated estrogens
14947:17β-Dihydroequilenin
14922:17α-Dihydroequilenin
14862:15α-Hydroxyestradiol
14857:11β-Methoxyestradiol
14832:8,9-Dehydroestradiol
14033:Potassium canrenoate
13501:Quingestanol acetate
13311:Tetrahydrogestrinone
13199:Metenolone enanthate
13025:5α-Dihydrotrestolone
13020:5α-Dihydronandrolone
13008:Trestolone enanthate
12976:Trenbolone enanthate
12942:Norclostebol acetate
12551:Clostebol propionate
12284:cellular respiration
10865:Fatty acid synthesis
10570:Amino acid synthesis
10294:7-Dehydrocholesterol
10154:Pregnenolone sulfate
9702:Testosterone sulfate
9662:Androsterone sulfate
9143:24-Methylenelophenol
9038:7-Dehydrodesmosterol
9016:7-Dehydrocholesterol
8458:Tetraprenylcurcumene
7939:Grapefruit mercaptan
7188:on 28 February 2009.
7161:. pp. 345–391.
6470:10.1210/er.2001-0038
5465:. Berlin: Springer.
4997:10.1128/AEM.00300-11
4610:Combustion and Flame
4249:10.1210/er.2010-0013
4148:(3): 436–437. 1989.
3875:(3): 429–458. 1989.
3409:10.1056/NEJMra050541
3228:Steroidogenic enzyme
2813:family of enzymes),
2770:Alternative pathways
2124:Steroidogenic enzyme
1985:farnesyl diphosphate
1838:cyanobacteriosponges
1748:Secosteroids (Latin
1360:that helps regulate
870:Species distribution
149:corticosteroid drug
20003:Etynodiol diacetate
19870:Nomegestrol acetate
19845:Gestadienol acetate
19695:Medroxyprogesterone
19595:Delmadinone acetate
19585:Cyproterone acetate
19555:Cismadinone acetate
19540:Chlormethenmadinone
19490:Algestone acetonide
18934:18-Deoxyaldosterone
18866:Prednisolone esters
18719:Cortodoxone acetate
18439:Cyproterone acetate
18229:Delmadinone acetate
18219:Cyproterone acetate
18044:Flunisolide acetate
17751:Fluticasone furoate
17695:Flumetasone acetate
17610:Cormetasone acetate
17586:Clocortolone esters
17489:Tixocortol pivalate
17426:Prednisolone esters
17314:Fluperolone acetate
17125:Cortodoxone acetate
16871:Propylpyrazoletriol
16786:Diarylpropionitrile
15634:Propylpyrazoletriol
15491:Dimethylstilbestrol
15457:Diarylpropionitrile
15267:Etynodiol diacetate
14967:Abiraterone acetate
14877:16α-Fluoroestradiol
14556:Dihydrotestosterone
14551:Dehydroandrosterone
14402:Ralaniten (EPI-002)
14283:Inocoterone acetate
14008:Nomegestrol acetate
13908:Delmadinone acetate
13898:Cyproterone acetate
13843:Abiraterone acetate
13813:7α-Thioprogesterone
13423:Etynodiol diacetate
12627:Testosterone esters
12570:Dehydroandrosterone
12467:11-Ketotestosterone
11456:Transcription &
10429:Aerobic respiration
10334:Cholesterol sulfate
10069:-Hydroxycholesterol
9961:estradiol palmitate
9943:Estriol glucuronide
9933:Estrone glucuronide
9903:Estradiol disulfate
9577:Dihydrotestosterone
9562:Dehydroandrosterone
9527:11-Ketotestosterone
9363:11-Ketoprogesterone
9277:-Hydroxycholesterol
9133:4α-methylfecosterol
9076:-Hydroxycholesterol
8241:Dehydroabietic acid
7707:(cyclopentane ring)
7585:Halogenated steroid
7035:Lednicer D (2011).
6796:10.1021/ja01267a513
6728:10.1021/ja01143a033
6603:1976ApEnM..32..310C
6349:10.1155/2010/625105
6272:. 19 January 2024.
6207:. 24 January 2022.
5948:10.2147/DDDT.S10812
5105:2003PChem..64....3W
4989:2011ApEnM..77.3905S
4651:(3): 429–58. 1989.
4622:2013CoFl..160.1484B
4164:. p. 436-437:
3370:Lednicer D (2011).
2929:Methods of analysis
2923:and small-molecule
2803:dihydrotestosterone
2778:(MEP pathway) uses
2263:
1484:cyproterone acetate
1475:pancuronium bromide
402:. The D ring has a
124:signaling molecules
29:Page version status
20549:Ulipristal acetate
20489:Asoprisnil ecamate
20469:Dihydroethisterone
20319:Trestolone acetate
20299:trenbolone acetate
20216:Dimethyltrienolone
19810:19-Norprogesterone
19755:Mometasone furoate
19720:Megestrol caproate
19610:Flugestone acetate
19565:Clogestone acetate
19520:Butagest (buterol)
19505:Anagestone acetate
18829:Mometasone furoate
18746:19-Norprogesterone
18549:Ulipristal acetate
18419:Asoprisnil ecamate
17899:Timobesone acetate
17836:Mometasone furoate
17372:Methylprednisolone
17171:Cloprednol acetate
16953:Diethylstilbestrol
16737:2-Methoxyestradiol
16668:TAS-108 (SR-16234)
16618:Methylepitiostanol
16556:EM-800 (SCH-57050)
16480:TAS-108 (SR-16234)
16200:2-Phenylbenzofuran
15814:8-prenylnaringenin
15474:Diethylstilbestrol
15132:Lipoidal estradiol
15107:ERA-63 (ORG-37663)
15049:Conjugated estriol
14994:methyltestosterone
14952:17β-Dihydroequilin
14927:17α-Dihydroequilin
14902:16β-Hydroxyestrone
14887:16α-Hydroxyestrone
14837:8,9-Dehydroestrone
14822:7α-Methylestradiol
14797:4-Methoxyestradiol
14787:4-Hydroxyestradiol
14762:3β-Hydroxytibolone
14757:3α-Hydroxytibolone
14727:2-Hydroxyestradiol
13393:Dihydroethisterone
13256:Dimethyltrienolone
13216:Methylepitiostanol
13194:Metenolone acetate
13127:Methyltestosterone
13030:19-Norandrosterone
13003:Trestolone acetate
12971:Trenbolone acetate
12915:-nitrosocarbamate)
12804:Stenbolone acetate
12694:Bolazine capronate
12546:Clostebol caproate
12243:metabolic pathways
10933:Ethanol metabolism
10881:Steroid metabolism
10606:Nucleotide salvage
10538:Protein metabolism
9957:estradiol stearate
9953:Lipoidal estradiol
9883:2-Methoxyestradiol
9808:16β-Hydroxyestrone
9803:16α-Hydroxyestrone
9793:4-Methoxyestradiol
9778:4-Hydroxyestradiol
9763:2-Hydroxyestradiol
9692:Epietiocholanolone
9642:3β-Etiocholanediol
9637:3α-Etiocholanediol
9433:Mineralocorticoids
9418:5α-Dihydrocortisol
8719:Mevalonate pathway
7701:Bicyclic (2 rings)
7039:. Hoboken: Wiley.
5900:10.1007/BF02537824
5812:10.1007/BF02703339
5402:Wolfing J (2007).
4940:10.1093/gbe/evp036
4715:Biology Libretexts
4039:. 11 August 2018.
3374:. Hoboken: Wiley.
3018:Dioscorea mexicana
2935:Chemical synthesis
2887:chemical structure
2630:<37–140 pmol/L
2590:<37–360 pmol/L
2416:<37–210 pmol/L
2236:
2222:(CNS) express the
2120:
2078:mevalonate pathway
2018:Mevalonate pathway
2014:
2012:Mevalonate pathway
2004:Mevalonate pathway
1924:
1871:are components of
1635:
1624:
1558:Intact ring system
1521:cardiac glycosides
1348:Mineralocorticoids
1241:mineralocorticoids
1197:, which influence
1136:cardiac glycosides
655:
641:
373:
368:Steroid 5α and 5β
362:
93:
68:Steroids (journal)
35:
20863:
20862:
20857:
20856:
20817:
20816:
20716:
20715:
20295:Trenbolone esters
20256:Nandrolone esters
20211:Dimethyldienolone
19820:Amadinone acetate
19765:Osaterone acetate
19715:Megestrol acetate
19510:Bromethenmadinone
19430:Retroprogesterone
19252:
19251:
19217:
19216:
18878:Prednisone esters
18805:Cortisone acetate
18620:
18619:
18585:
18584:
18299:Osaterone acetate
18284:Megestrol acetate
17995:Desonide pivalate
17438:Prednisone esters
17227:Cortisone acetate
17006:
17005:
16998:List of estrogens
16966:
16965:
16711:
16710:
16551:Cytestrol acetate
15774:isoliquiritigenin
15716:Unknown/unsorted:
15402:β-LGND2 (GTx-878)
14982:Anabolic steroids
14892:16α-Iodoestradiol
14782:4-Fluoroestradiol
14777:4-Androstenedione
14767:3β-Androstanediol
14742:3α-Androstanediol
14693:Estrogen receptor
14659:
14658:
14619:
14618:
14589:
14582:
14575:
14568:
14500:
14499:
14023:Osaterone acetate
13983:Megestrol acetate
13848:Allyltestosterone
13624:Acetothiolutamide
13543:Megestrol acetate
13346:Vinyltestosterone
13251:Dimethyldienolone
13070:Ethyltestosterone
12998:Trestolone (MENT)
12930:Nandrolone esters
12911:-(2-chloroethyl)-
12787:Nisterime acetate
12664:3α-Androstanediol
12649:1-Androstenedione
12558:Cloxotestosterone
12541:Clostebol acetate
12462:5-Androstenedione
12408:Androgen receptor
12369:Steroid signaling
12361:
12360:
12231:
12230:
12191:Neurotransmitters
11570:Nucleotide sugars
11303:Direct / C4 / CAM
10950:
10949:
10946:
10945:
10909:
10908:
10822:
10821:
10818:
10817:
10805:Xylose metabolism
10751:
10750:
10624:
10623:
10601:Purine metabolism
10546:Protein synthesis
10523:
10522:
10445:Citric acid cycle
10403:Metabolic network
10398:Metabolic pathway
10342:
10341:
10179:3α-Androstanediol
10048:
10047:
9923:Estradiol sulfate
9843:4-Androstenedione
9838:3β-Androstanediol
9833:3α-Androstanediol
9627:3β-Androstanediol
9617:3α-Androstanediol
9499:
9498:
9373:21-Deoxycortisone
9215:
9214:
9211:
9210:
8962:2,3-Oxidosqualene
8937:
8936:
8876:
8875:
8670:
8669:
8618:7,8-dihydroionone
8577:
8576:
8444:
8443:
8281:
8280:
8249:Lambertianic acid
8023:
8022:
7872:
7871:
7687:Acyclic (linear,
7630:
7629:
7615:Elements replaced
7178:"Steroidogenesis"
7168:978-1-4832-1956-1
7081:10.1021/cr040623l
7054:978-0-470-66085-0
7007:978-0-85404-464-1
6790:(12): 3592–3593.
6760:978-94-011-7605-7
6722:(23): 5933–5936.
6700:978-3-527-30673-2
6647:Mycobacterium sp.
6571:978-1-4020-9774-4
6457:Endocrine Reviews
6430:10.1021/mp060010s
6253:978-3-319-44557-1
6238:. pp. 1–17.
5837:on 15 April 2007.
5615:10.1002/ijc.30450
5579:978-1-4292-4646-0
5546:978-0-321-98122-6
5480:978-3-642-34064-2
5262:978-1-4408-0299-7
5170:978-0-88192-952-2
5145:978-0-88192-952-2
5077:978-1-119-37431-2
5039:978-3-319-48683-3
4711:"17.2C: Steroids"
4591:978-0-85404-182-4
4198:978-0-85404-182-4
4081:978-0-85404-182-4
4018:978-0-85404-182-4
3728:978-3-540-57420-0
3695:978-0-8493-6415-0
3659:978-0-412-27060-4
3403:(16): 1711–1723.
3381:978-0-470-66084-3
3271:(10): 1783–1822.
3160:1975 (Chemistry)
3149:1969 (Chemistry)
3135:1965 (Chemistry)
3123:Tadeus Reichstein
3099:1939 (Chemistry)
3092:1928 (Chemistry)
3007:. The efforts of
2976:biotransformation
2972:organic synthesis
2968:functional groups
2897:, precipitation,
2833:enzymes, such as
2809:(a member of the
2767:
2766:
2730:Notes and sources
2688:Follicular phase
2675:1100–7300 pmol/L
2643:Follicular phase
2578:Follicular phase
2513:Follicular phase
2190:primarily in the
1989:squalene synthase
1877:membrane fluidity
1715:
1714:
1617:
1597:
1596:
1358:mineralocorticoid
1341:immunosuppression
1310:
1309:
1255:Anabolic steroids
1076:ultraviolet light
1037:azole antifungals
978:
977:
914:
913:
690:functional groups
664:Naming convention
661:
660:
576:within the rings,
319:is an endogenous
238:functional groups
147:anti-inflammatory
143:anabolic steroids
120:membrane fluidity
47:19 September 2024
26:
16:(Redirected from
20888:
20778:Allopregnanolone
20743:
20742:
20738:
20734:
20728:
20724:
20458:
20454:
19650:Haloprogesterone
19307:
19306:
19303:
19299:
19279:
19272:
19265:
19256:
19255:
18675:
18674:
18671:
18667:
18647:
18640:
18633:
18624:
18623:
18363:
18359:
17673:Dimesone acetate
17154:Chloroprednisone
17132:21-Deoxycortisol
17061:
17060:
17057:
17053:
17033:
17026:
17019:
17010:
17009:
16865:2,2',5'-PCB-4-OH
16801:Ethinylestradiol
16727:
16726:
16723:
16719:
16460:Rimostil (P-081)
16270:Chlorotrianisene
16192:
16188:
15967:Metalloestrogens
15746:-related (e.g.,
15561:Hexestrol esters
15235:Ethinylestradiol
15127:Estradiol esters
14882:16α-Hydroxy-DHEA
14867:16-Ketoestradiol
14807:5-Androstenediol
14802:4-Methoxyestrone
14792:4-Hydroxyestrone
14772:4-Androstenediol
14732:2-Hydroxyestrone
14714:
14713:
14710:
14706:
14686:
14679:
14672:
14663:
14662:
14607:
14603:
14587:
14580:
14573:
14566:
14511:
14510:
14293:Ketodarolutamide
14273:Hydroxyflutamide
14230:(via metabolite
13599:
13595:
13550:Others/unsorted:
13221:Methylstenbolone
13085:Hydroxystenozole
12644:1-Androstenediol
12442:4-Androstenediol
12429:
12428:
12425:
12421:
12401:
12394:
12387:
12378:
12377:
12365:
12364:
12355:
12352:lipid metabolism
12349:
12348:
12343:
12333:
12332:
12327:
12317:
12316:
12311:
12305:
12304:
12299:
12293:
12292:
12287:
12281:
12280:
12275:
12269:
12268:
12263:
12257:
12256:
12239:
12238:
12221:
12214:
12205:
12198:
12196:thyroid hormones
12186:
12177:
12170:
12163:
12154:
12145:
12138:
12131:
12122:
12115:
12108:
12091:
12082:
12075:
12066:
12059:
12052:
12045:
12033:
12026:
12017:
12010:
12003:
11996:
11984:
11977:
11955:
11942:
11929:
11920:
11905:
11898:
11889:
11882:
11869:
11856:
11849:
11842:
11828:
11816:
11809:
11795:
11781:
11772:
11763:
11756:
11749:
11740:
11731:
11722:
11713:
11706:
11697:
11690:
11681:
11674:
11667:
11660:
11653:
11646:
11639:
11630:
11623:
11614:
11607:
11600:
11593:
11586:
11579:
11572:
11565:
11553:
11546:
11537:
11520:
11508:
11504:
11493:
11489:
11480:
11476:
11467:
11463:
11457:
11448:
11444:
11433:
11429:
11420:
11416:
11407:
11403:
11394:
11390:
11381:
11377:
11368:
11364:
11353:
11349:
11338:
11334:
11323:
11319:
11310:
11306:
11295:
11291:
11278:
11274:
11263:
11259:
11248:
11244:
11235:
11231:
11218:
11214:
11203:
11199:
11188:
11184:
11173:
11169:
11155:
11152:
11142:
11139:
11131:
11128:
11118:
11115:
11103:
11100:
11088:
11085:
11075:
11072:
11062:
11059:
11049:
11046:
11034:
11031:
11021:
11018:
11006:
10995:
10977:
10970:
10963:
10954:
10953:
10921:Metal metabolism
10843:
10842:
10828:Lipid metabolism
10760:
10759:
10653:
10652:
10646:
10645:
10558:
10557:
10534:
10533:
10460:
10425:
10424:
10369:
10362:
10355:
10346:
10345:
10109:Allopregnanolone
10025:Allopregnanediol
9898:4-Methoxyestriol
9893:2-Methoxyestriol
9888:2-Methoxyestrone
9873:16α-Hydroxy-DHEA
9848:5-Androstenediol
9813:16-Ketoestradiol
9798:4-Methoxyestrone
9788:4-Hydroxyestrone
9783:4-Hydroxyestriol
9773:2-Hydroxyestrone
9768:2-Hydroxyestriol
9677:Etiocholanedione
9647:Androstanetriols
9597:16α-Hydroxy-DHEA
9510:
9509:
9451:11-Deoxycortisol
9368:21-Deoxycortisol
9358:11-Deoxycortisol
9331:
9330:
9242:
9235:
9228:
9219:
9218:
9193:Ergostatetraenol
9105:
9104:
9064:Steroid hormones
8887:
8886:
8780:Acetoacetic acid
8724:
8723:
8697:
8690:
8683:
8674:
8673:
8478:
8477:
8310:
8309:
8287:Sesterterpenoids
8253:Levopimaric acid
8115:Geranyl-linalool
8096:
8095:
8029:Sesquiterpenoids
7969:Perillyl alcohol
7883:
7882:
7778:
7777:
7657:
7650:
7643:
7634:
7633:
7594:Elements removed
7567:Functional group
7379:Androstenetrione
7296:Estratrienetriol
7218:
7211:
7204:
7195:
7194:
7189:
7172:
7159:Elsevier Science
7144:
7102:
7092:
7069:Chemical Reviews
7058:
7031:
7029:
7027:
7011:
6982:
6981:
6979:
6977:
6962:
6956:
6955:
6953:
6951:
6936:
6930:
6929:
6927:
6925:
6910:
6904:
6903:
6901:
6899:
6884:
6878:
6877:
6875:
6873:
6858:
6852:
6851:
6849:
6847:
6832:
6826:
6825:
6823:
6821:
6806:
6800:
6799:
6779:
6773:
6772:
6738:
6732:
6731:
6711:
6705:
6704:
6678:
6667:
6666:
6642:
6633:
6632:
6622:
6582:
6576:
6575:
6562:Steroid analysis
6556:
6547:
6546:
6544:
6542:
6523:
6514:
6513:
6511:
6509:
6489:
6483:
6482:
6472:
6448:
6442:
6441:
6413:
6407:
6406:
6378:
6372:
6371:
6361:
6351:
6327:
6321:
6320:
6292:
6286:
6285:
6283:
6281:
6264:
6258:
6257:
6227:
6221:
6220:
6218:
6216:
6201:
6195:
6194:
6166:
6160:
6159:
6149:
6125:
6114:
6113:
6111:
6109:
6061:
6055:
6054:
6044:
6020:
6014:
6013:
5977:
5971:
5970:
5960:
5950:
5926:
5920:
5919:
5883:
5877:
5876:
5848:
5839:
5838:
5836:
5830:. Archived from
5797:
5788:
5782:
5781:
5770:10.1039/b109860h
5753:
5744:
5743:
5733:
5715:
5691:
5685:
5684:
5674:
5642:
5636:
5635:
5617:
5593:
5584:
5583:
5565:
5559:
5558:
5532:
5526:
5525:
5523:
5514:(6): 1093–1111.
5499:
5493:
5492:
5454:
5448:
5447:
5445:
5443:
5433:
5423:
5399:
5393:
5392:
5390:
5388:
5373:
5367:
5366:
5355:10.1039/c001262a
5338:
5332:
5331:
5303:
5297:
5296:
5294:
5292:
5273:
5267:
5266:
5251:Zorea A (2014).
5248:
5242:
5241:
5239:
5237:
5222:
5216:
5215:
5205:
5181:
5175:
5174:
5156:
5150:
5149:
5131:
5125:
5124:
5088:
5082:
5081:
5063:
5044:
5043:
5025:
5019:
5018:
5008:
4968:
4962:
4961:
4951:
4919:
4913:
4912:
4875:
4869:
4868:
4858:
4848:
4824:
4818:
4817:
4811:
4803:
4801:
4799:
4788:
4782:
4781:
4771:
4761:
4737:
4731:
4730:
4728:
4726:
4707:
4701:
4700:
4698:
4696:
4679:
4673:
4672:
4640:
4634:
4633:
4616:(8): 1484–1498.
4605:
4599:
4598:
4594:. p. 1112:
4569:
4563:
4562:
4526:
4520:
4519:
4509:
4477:
4471:
4470:
4460:
4450:
4426:
4420:
4419:
4399:
4393:
4392:
4356:
4350:
4349:
4329:
4323:
4322:
4320:
4318:
4303:
4297:
4296:
4294:
4292:
4277:
4271:
4270:
4260:
4228:
4207:
4206:
4176:
4170:
4169:
4137:
4128:
4127:
4107:(3): 430. 1989.
4096:
4090:
4089:
4059:
4053:
4052:
4050:
4048:
4033:
4027:
4026:
3996:
3990:
3989:
3957:
3951:
3950:
3944:
3942:
3903:
3897:
3896:
3864:
3855:
3854:
3833:(3): 430. 1989.
3822:
3816:
3809:
3803:
3793:
3775:
3766:
3745:
3739:
3733:
3732:
3710:
3704:
3703:
3677:
3671:
3670:
3668:
3666:
3642:
3636:
3635:
3625:
3615:
3591:
3585:
3584:
3582:
3580:
3565:
3559:
3558:
3537:
3531:
3530:
3528:
3526:
3499:
3493:
3492:
3490:
3488:
3468:
3462:
3461:
3459:
3457:
3438:
3429:
3428:
3392:
3386:
3385:
3367:
3356:
3355:
3353:
3351:
3333:
3303:
3301:
3299:
3293:
3265:Pure Appl. Chem.
3261:
3252:
3198:List of steroids
3131:adrenal hormones
2869:with sulfate or
2761:
2655:700–3600 pmol/L
2610:699–1250 pmol/L
2473:3.1–12.2 nmol/L
2443:600–2500 pmol/L
2362:6.9–34.7 nmol/L
2307:
2300:
2280:production rate
2264:
2257:
2250:
2243:
2235:
2106:
2055:natural products
1906:(PP or IPP) and
1754:biosynthetically
1637:
1636:
1615:
1592:
1589:
1570:
1562:
1463:taurocholic acid
1454:allopregnanolone
1451:
1447:
1394:and maintains a
1314:steroid hormones
1305:
1302:
1283:
1275:
1205:. These include
1172:steroid hormones
1144:brassinosteroids
1029:antifungal drugs
973:
970:
964:
944:
936:
909:
906:
900:
882:
881:
874:
737:11-deoxycortisol
635:and key steroid
616:
615:
544:
529:
514:
491:
472:
445:
435:anabolic steroid
423:
294:
282:
264:one of which is
101:organic compound
64:Anabolic steroid
21:
20896:
20895:
20891:
20890:
20889:
20887:
20886:
20885:
20866:
20865:
20864:
20859:
20858:
20853:
20813:
20797:
20736:
20729:
20726:
20712:
20598:
20456:
20449:
20443:
20270:Norethandrolone
20231:Methyldienolone
20191:Dimethandrolone
19615:Fluorometholone
19301:
19291:
19283:
19253:
19248:
19213:
19084:SC-11927 (CS-1)
18884:
18669:
18659:
18651:
18621:
18616:
18581:
18576:
18558:
18399:7α-Hydroxy-DHEA
18385:
18361:
18354:
18348:
18264:Fluoxymesterone
17321:Fluprednisolone
17297:Fluorometholone
17055:
17045:
17037:
17007:
17002:
16962:
16941:
16905:
16721:
16707:
16541:7β-Hydroxy-DHEA
16524:
16360:Levormeloxifene
16190:
16183:
16177:
16093:deoxymiroestrol
15961:-hinokiresinol)
15599:Methallenestril
15501:Doisynolic acid
15302:Methylestradiol
14817:7α-Hydroxy-DHEA
14708:
14698:
14690:
14660:
14655:
14615:
14605:
14496:
14218:Cyanonilutamide
14147:Bavdegalutamide
13958:Epitestosterone
13798:
13629:Acetoxolutamide
13597:
13587:
13296:Norethandrolone
13271:Methyldienolone
13075:Fluoxymesterone
12885:Dimethandrolone
12745:Epiandrosterone
12423:
12413:
12405:
12370:
12362:
12357:
12356:
12346:
12344:
12330:
12328:
12314:
12312:
12302:
12300:
12290:
12288:
12278:
12276:
12266:
12264:
12254:
12252:
12250:
12247:metro-style map
12240:
12232:
12227:
12226:
12225:
12224:
12223:
12222:
12217:
12215:
12211:
12208:
12206:
12201:
12199:
12193:
12189:
12187:
12183:
12182:Polyunsaturated
12180:
12178:
12173:
12171:
12166:
12164:
12160:
12157:
12155:
12151:
12148:
12146:
12141:
12139:
12134:
12132:
12128:
12125:
12123:
12118:
12116:
12111:
12109:
12098:
12094:
12092:
12088:
12085:
12083:
12078:
12076:
12072:
12069:
12067:
12062:
12060:
12055:
12053:
12048:
12046:
12040:
12036:
12034:
12029:
12027:
12023:
12020:
12018:
12013:
12011:
12006:
12004:
11999:
11997:
11991:
11987:
11985:
11980:
11978:
11967:
11958:
11956:
11949:
11945:
11943:
11936:
11932:
11930:
11926:
11923:
11921:
11917:
11908:
11906:
11901:
11899:
11895:
11892:
11890:
11885:
11883:
11876:
11872:
11870:
11862:
11859:
11857:
11852:
11850:
11845:
11843:
11839:
11836:
11831:
11829:
11823:
11819:
11817:
11812:
11810:
11804:
11801:
11798:
11796:
11790:
11787:
11784:
11782:
11778:
11775:
11773:
11769:
11766:
11764:
11759:
11757:
11752:
11750:
11746:
11743:
11741:
11737:
11734:
11732:
11728:
11725:
11723:
11719:
11716:
11714:
11709:
11707:
11703:
11700:
11698:
11693:
11691:
11687:
11684:
11682:
11677:
11675:
11670:
11668:
11663:
11661:
11656:
11654:
11649:
11647:
11642:
11640:
11636:
11633:
11631:
11626:
11624:
11620:
11617:
11615:
11610:
11608:
11603:
11601:
11596:
11594:
11589:
11587:
11582:
11580:
11575:
11573:
11568:
11566:
11560:
11556:
11554:
11549:
11547:
11543:
11540:
11538:
11530:
11523:
11521:
11517:
11514:
11511:
11509:
11502:
11500:
11496:
11494:
11487:
11483:
11481:
11474:
11470:
11468:
11461:
11459:
11455:
11451:
11449:
11442:
11440:
11436:
11434:
11427:
11423:
11421:
11414:
11410:
11408:
11402:Steroidogenesis
11401:
11397:
11395:
11388:
11384:
11382:
11375:
11371:
11369:
11362:
11360:
11356:
11354:
11347:
11345:
11341:
11339:
11333:phosphorylation
11332:
11330:
11326:
11324:
11317:
11313:
11311:
11304:
11302:
11298:
11296:
11289:
11287:
11285:
11281:
11279:
11272:
11270:
11266:
11264:
11257:
11255:
11251:
11249:
11242:
11238:
11236:
11229:
11227:
11225:
11221:
11219:
11212:
11210:
11206:
11204:
11197:
11195:
11191:
11189:
11182:
11180:
11176:
11174:
11167:
11165:
11161:
11158:
11156:
11150:
11148:
11145:
11143:
11137:
11134:
11132:
11126:
11124:
11121:
11119:
11113:
11111:
11109:
11106:
11104:
11098:
11096:
11094:
11091:
11089:
11083:
11081:
11078:
11076:
11070:
11068:
11065:
11063:
11057:
11055:
11052:
11050:
11044:
11042:
11040:
11037:
11035:
11029:
11027:
11024:
11022:
11016:
11014:
11011:
11007:
10987:
10981:
10951:
10942:
10926:Iron metabolism
10905:
10869:
10830:
10814:
10796:
10782:Carbon fixation
10747:
10722:
10685:
10668:
10664:Gluconeogenesis
10637:
10632:
10620:
10592:
10585:
10556:
10529:
10519:
10480:
10464:
10452:
10419:
10412:
10386:
10373:
10343:
10338:
10309:Cholecalciferol
10276:
10257:Androstadienone
10229:Etiocholanolone
10199:7β-Hydroxy-DHEA
10194:7α-Hydroxy-DHEA
10139:Isopregnanolone
10134:Epipregnanolone
10044:
9966:
9948:Estriol sulfate
9938:Estrone sulfate
9868:7α-Hydroxy-DHEA
9706:
9682:Etiocholanolone
9587:Epitestosterone
9582:Epiandrosterone
9552:Androstenedione
9495:
9427:
9335:Glucocorticoids
9326:Corticosteroids
9320:
9254:
9246:
9216:
9207:
9163:
9096:
9061:
9052:
8933:
8872:
8849:
8828:
8789:
8761:
8742:Acetoacetyl-CoA
8713:
8701:
8671:
8666:
8643:
8621:
8604:
8573:
8529:
8469:
8467:Tetraterpenoids
8461:
8440:
8381:
8372:Cholecalciferol
8298:
8295:Geranylfarnesol
8277:
8260:Neoabietic acid
8245:Isopimaric acid
8220:
8194:
8164:
8139:
8118:
8084:
8019:
7978:
7927:
7878:
7877:Monoterpenoids
7868:
7823:
7797:
7773:
7769:
7765:
7757:
7753:Isovaleric acid
7743:
7739:
7719:
7676:
7661:
7631:
7626:
7610:
7589:
7561:
7550:
7542:
7526:
7518:
7507:
7499:
7445:Dehydrogenated:
7434:
7426:
7415:
7407:
7399:Androstadienone
7374:Androstenedione
7369:Androstanedione
7319:Dehydrogenated:
7308:
7300:
7291:Estratrienediol
7286:Estratrienolone
7266:Dehydrogenated:
7255:
7247:
7236:
7228:
7222:
7192:
7169:
7151:"Cortoic acids"
7075:(12): 4730–56.
7055:
7025:
7023:
7014:
7008:
6991:
6986:
6985:
6975:
6973:
6964:
6963:
6959:
6949:
6947:
6938:
6937:
6933:
6923:
6921:
6912:
6911:
6907:
6897:
6895:
6886:
6885:
6881:
6871:
6869:
6860:
6859:
6855:
6845:
6843:
6834:
6833:
6829:
6819:
6817:
6808:
6807:
6803:
6780:
6776:
6761:
6739:
6735:
6712:
6708:
6701:
6679:
6670:
6643:
6636:
6583:
6579:
6572:
6557:
6550:
6540:
6538:
6525:
6524:
6517:
6507:
6505:
6490:
6486:
6449:
6445:
6414:
6410:
6379:
6375:
6328:
6324:
6293:
6289:
6279:
6277:
6266:
6265:
6261:
6254:
6228:
6224:
6214:
6212:
6203:
6202:
6198:
6167:
6163:
6126:
6117:
6107:
6105:
6062:
6058:
6021:
6017:
5978:
5974:
5927:
5923:
5884:
5880:
5849:
5842:
5834:
5795:
5789:
5785:
5754:
5747:
5692:
5688:
5643:
5639:
5594:
5587:
5580:
5566:
5562:
5547:
5533:
5529:
5508:Pure Appl. Chem
5500:
5496:
5481:
5459:"Nakiterpiosin"
5455:
5451:
5441:
5439:
5400:
5396:
5386:
5384:
5375:
5374:
5370:
5339:
5335:
5304:
5300:
5290:
5288:
5275:
5274:
5270:
5263:
5249:
5245:
5235:
5233:
5224:
5223:
5219:
5182:
5178:
5171:
5157:
5153:
5146:
5132:
5128:
5089:
5085:
5078:
5064:
5047:
5040:
5026:
5022:
4983:(12): 3905–15.
4969:
4965:
4920:
4916:
4876:
4872:
4825:
4821:
4805:
4804:
4797:
4795:
4790:
4789:
4785:
4738:
4734:
4724:
4722:
4717:. 3 July 2018.
4709:
4708:
4704:
4694:
4692:
4681:
4680:
4676:
4667:. p. 430:
4642:
4641:
4637:
4606:
4602:
4592:
4570:
4566:
4527:
4523:
4478:
4474:
4427:
4423:
4400:
4396:
4357:
4353:
4330:
4326:
4316:
4314:
4305:
4304:
4300:
4290:
4288:
4279:
4278:
4274:
4229:
4210:
4199:
4177:
4173:
4139:
4138:
4131:
4123:. p. 430:
4098:
4097:
4093:
4082:
4060:
4056:
4046:
4044:
4035:
4034:
4030:
4021:. p. 868:
4019:
3997:
3993:
3984:. p. 431:
3959:
3958:
3954:
3940:
3938:
3905:
3904:
3900:
3891:. p. 441:
3866:
3865:
3858:
3849:. p. 430:
3824:
3823:
3819:
3773:
3767:
3748:
3740:
3736:
3729:
3711:
3707:
3696:
3678:
3674:
3664:
3662:
3660:
3643:
3639:
3592:
3588:
3578:
3576:
3567:
3566:
3562:
3538:
3534:
3524:
3522:
3500:
3496:
3486:
3484:
3469:
3465:
3455:
3453:
3452:on 8 March 2011
3440:
3439:
3432:
3393:
3389:
3382:
3368:
3359:
3349:
3347:
3338:
3307:
3297:
3295:
3291:
3259:
3253:
3242:
3237:
3232:
3178:
3162:Vladimir Prelog
3105:Leopold Ružička
3101:Adolf Butenandt
3071:
3069:Research awards
3039:total synthesis
3035:
3033:Total synthesis
2989:
2984:
2952:17-ketosteroids
2937:
2925:crystallography
2907:crystallization
2879:
2871:glucuronic acid
2827:
2811:cytochrome P450
2772:
2763:
2762:
2753:production rate
2733:
2731:
2678:400–2600 pg/mL
2658:250–1300 pg/mL
2639:Estrone sulfate
2545:310–660 pmol/L
2525:110–400 pmol/L
2500:0.7–2.8 nmol/L
2488:
2461:
2455:Androstenedione
2431:
2425:Estrone sulfate
2404:
2377:
2365:200–1000 ng/dL
2350:
2335:2.8–7.3 nmol/L
2323:
2317:Androstenedione
2290:clearance rate
2289:
2285:secretion rate
2284:
2279:
2274:
2261:
2205:prostate cancer
2138:corticosteroids
2126:
2108:
2105:Steroidogenesis
2094:bisphosphonates
2072:Two classes of
2020:
2006:
1896:
1888:prostate cancer
1861:
1766:
1759:cholecalciferol
1746:
1728:
1724:
1720:
1618:
1611:Cholecalciferol
1593:
1587:
1584:
1577:needs expansion
1571:
1560:
1555:
1543:cholecalciferol
1449:
1327:Glucocorticoids
1321:Corticosteroids
1306:
1300:
1297:
1290:needs expansion
1284:
1273:
1268:
1237:immune function
1229:glucocorticoids
1225:natural product
1221:Corticosteroids
1199:sex differences
1188:atherosclerosis
1186:(implicated in
1152:
1116:
1021:
974:
968:
965:
958:
945:
934:
910:
904:
901:
895:
883:
879:
872:
800:androstenedione
718:stereochemistry
666:
558:
555:
545:
536:
530:
521:
515:
506:
505:classification.
492:
483:
473:
464:
461:hydroxyl groups
459:and additional
457:carboxylic acid
446:
437:
424:
351:
341:
336:
331:
330:
329:
328:
321:steroid hormone
300:
299:
298:
295:
287:
286:
283:
269:
242:oxidation state
133:, sex hormones
75:
60:
55:
54:
53:
52:
51:
50:
34:
22:
15:
12:
11:
5:
20894:
20884:
20883:
20878:
20861:
20860:
20855:
20854:
20852:
20851:
20846:
20841:
20836:
20831:
20826:
20822:
20819:
20818:
20815:
20814:
20812:
20811:
20805:
20803:
20799:
20798:
20796:
20795:
20790:
20785:
20780:
20775:
20770:
20765:
20760:
20755:
20749:
20747:
20740:
20718:
20717:
20714:
20713:
20711:
20710:
20705:
20700:
20695:
20690:
20685:
20680:
20675:
20670:
20661:
20660:
20655:
20650:
20645:
20640:
20635:
20630:
20625:
20620:
20615:
20606:
20604:
20600:
20599:
20597:
20596:
20591:
20586:
20581:
20576:
20571:
20562:
20561:
20556:
20551:
20546:
20541:
20536:
20531:
20526:
20521:
20516:
20511:
20506:
20501:
20496:
20491:
20486:
20481:
20476:
20471:
20462:
20460:
20445:
20444:
20442:
20441:
20436:
20427:
20426:
20421:
20416:
20411:
20406:
20401:
20396:
20391:
20386:
20377:
20376:
20371:
20369:Spironolactone
20366:
20361:
20356:
20351:
20346:
20341:
20336:
20331:
20329:Canrenoic acid
20322:
20321:
20316:
20311:
20306:
20292:
20287:
20282:
20277:
20272:
20267:
20253:
20248:
20243:
20238:
20233:
20228:
20223:
20221:Ethyldienolone
20218:
20213:
20208:
20203:
20198:
20193:
20188:
20183:
20178:
20176:Dimethisterone
20173:
20168:
20163:
20158:
20153:
20148:
20143:
20138:
20129:
20124:
20119:
20114:
20109:
20104:
20102:Norvinisterone
20099:
20097:Norgestrienone
20094:
20089:
20084:
20079:
20074:
20060:
20055:
20053:Norelgestromin
20050:
20045:
20040:
20035:
20030:
20020:
20018:Levonorgestrel
20015:
20010:
20005:
20000:
19995:
19990:
19985:
19980:
19979:
19978:
19968:
19963:
19958:
19953:
19948:
19943:
19938:
19933:
19928:
19923:
19913:
19912:
19907:
19902:
19897:
19892:
19887:
19882:
19877:
19872:
19867:
19862:
19857:
19852:
19847:
19842:
19837:
19832:
19827:
19822:
19817:
19812:
19807:
19802:
19793:
19792:
19787:
19782:
19777:
19772:
19767:
19762:
19757:
19752:
19747:
19742:
19737:
19735:Methenmadinone
19732:
19727:
19722:
19717:
19712:
19707:
19702:
19697:
19692:
19687:
19682:
19677:
19672:
19667:
19662:
19657:
19652:
19647:
19642:
19637:
19632:
19627:
19622:
19617:
19612:
19607:
19602:
19597:
19592:
19587:
19582:
19577:
19572:
19567:
19562:
19557:
19552:
19547:
19542:
19537:
19532:
19527:
19522:
19517:
19512:
19507:
19502:
19497:
19492:
19487:
19482:
19477:
19472:
19467:
19462:
19457:
19452:
19443:
19442:
19437:
19432:
19427:
19425:Dydrogesterone
19422:
19417:
19412:
19407:
19398:
19397:
19392:
19387:
19382:
19377:
19372:
19367:
19362:
19357:
19352:
19347:
19342:
19337:
19332:
19327:
19322:
19313:
19311:
19304:
19293:
19292:
19282:
19281:
19274:
19267:
19259:
19250:
19249:
19247:
19246:
19241:
19236:
19231:
19226:
19222:
19219:
19218:
19215:
19214:
19212:
19211:
19206:
19201:
19196:
19191:
19186:
19181:
19176:
19171:
19166:
19161:
19156:
19151:
19146:
19137:
19136:
19131:
19126:
19121:
19116:
19111:
19106:
19104:Spironolactone
19101:
19096:
19091:
19086:
19081:
19076:
19071:
19066:
19061:
19056:
19051:
19046:
19041:
19036:
19031:
19026:
19021:
19016:
19011:
19006:
19001:
18996:
18991:
18986:
18981:
18976:
18974:Dydrogesterone
18971:
18966:
18964:Dimethisterone
18961:
18956:
18951:
18946:
18941:
18936:
18931:
18926:
18921:
18916:
18911:
18906:
18901:
18892:
18890:
18886:
18885:
18883:
18882:
18881:
18880:
18870:
18869:
18868:
18863:
18858:
18853:
18848:
18843:
18833:
18832:
18831:
18821:
18820:
18819:
18809:
18808:
18807:
18797:
18796:
18795:
18790:
18785:
18777:hydrocortisone
18770:
18769:
18768:
18763:
18756:Corticosterone
18753:
18748:
18743:
18738:
18733:
18728:
18723:
18722:
18721:
18716:
18706:
18705:
18704:
18694:
18693:
18692:
18681:
18679:
18672:
18661:
18660:
18650:
18649:
18642:
18635:
18627:
18618:
18617:
18615:
18614:
18609:
18604:
18599:
18594:
18590:
18587:
18586:
18583:
18582:
18580:
18579:
18574:
18566:
18564:
18560:
18559:
18557:
18556:
18551:
18546:
18541:
18536:
18531:
18526:
18521:
18516:
18511:
18506:
18501:
18496:
18491:
18486:
18481:
18476:
18471:
18466:
18461:
18456:
18451:
18446:
18441:
18436:
18431:
18426:
18421:
18416:
18411:
18406:
18401:
18395:
18393:
18387:
18386:
18384:
18383:
18378:
18373:
18367:
18365:
18350:
18349:
18347:
18346:
18341:
18332:
18331:
18326:
18321:
18316:
18311:
18306:
18301:
18296:
18291:
18286:
18281:
18276:
18271:
18266:
18261:
18256:
18251:
18246:
18241:
18236:
18231:
18226:
18221:
18216:
18211:
18206:
18201:
18196:
18187:
18186:
18181:
18176:
18171:
18166:
18165:
18164:
18154:
18149:
18144:
18139:
18130:
18129:
18124:
18119:
18118:
18117:
18112:
18102:
18097:
18096:
18095:
18085:
18080:
18075:
18070:
18069:
18068:
18063:
18058:
18048:
18047:
18046:
18036:
18031:
18026:
18021:
18016:
18015:
18014:
18004:
17999:
17998:
17997:
17992:
17982:
17977:
17972:
17967:
17962:
17957:
17952:
17947:
17942:
17933:
17932:
17927:
17926:
17925:
17915:
17914:
17913:
17903:
17902:
17901:
17891:
17890:
17889:
17879:
17874:
17873:
17872:
17862:
17861:
17860:
17855:
17850:
17840:
17839:
17838:
17828:
17827:
17826:
17821:
17811:
17810:
17809:
17799:
17798:
17797:
17787:
17782:
17781:
17780:
17770:
17765:
17760:
17759:
17758:
17753:
17745:
17744:
17743:
17733:
17732:
17731:
17721:
17720:
17719:
17709:
17704:
17703:
17702:
17697:
17687:
17682:
17677:
17676:
17675:
17665:
17664:
17663:
17658:
17651:Diflucortolone
17648:
17647:
17646:
17636:
17635:
17634:
17624:
17619:
17614:
17613:
17612:
17602:
17601:
17600:
17590:
17589:
17588:
17578:
17577:
17576:
17566:
17565:
17564:
17554:
17549:
17548:
17547:
17542:
17532:
17531:
17530:
17520:
17515:
17514:
17513:
17503:
17494:
17493:
17492:
17491:
17486:
17485:
17484:
17469:
17464:
17459:
17458:
17457:
17452:
17442:
17441:
17440:
17430:
17429:
17428:
17423:
17418:
17413:
17408:
17403:
17393:
17392:
17391:
17381:
17380:
17379:
17369:
17364:
17359:
17354:
17353:
17352:
17342:
17341:
17340:
17330:
17329:
17328:
17318:
17317:
17316:
17306:
17305:
17304:
17294:
17293:
17292:
17282:
17281:
17280:
17270:
17265:
17260:
17259:
17258:
17253:
17243:
17242:
17241:
17231:
17230:
17229:
17219:
17218:
17217:
17212:
17207:
17199:hydrocortisone
17192:
17191:
17190:
17185:
17178:Corticosterone
17175:
17174:
17173:
17163:
17162:
17161:
17151:
17146:
17145:
17144:
17137:Δ-Prednisolone
17134:
17129:
17128:
17127:
17122:
17112:
17111:
17110:
17100:
17099:
17098:
17088:
17083:
17078:
17069:
17067:
17058:
17047:
17046:
17036:
17035:
17028:
17021:
17013:
17004:
17003:
17001:
17000:
16995:
16990:
16985:
16980:
16975:
16971:
16968:
16967:
16964:
16963:
16961:
16960:
16955:
16949:
16947:
16943:
16942:
16940:
16939:
16934:
16929:
16924:
16919:
16913:
16911:
16907:
16906:
16904:
16903:
16898:
16893:
16888:
16883:
16878:
16873:
16868:
16858:
16853:
16848:
16843:
16838:
16833:
16831:Hydroxytyrosol
16828:
16823:
16818:
16813:
16808:
16803:
16798:
16793:
16788:
16783:
16769:
16764:
16759:
16754:
16749:
16744:
16739:
16733:
16731:
16724:
16713:
16712:
16709:
16708:
16706:
16705:
16696:
16695:
16686:
16685:
16680:
16675:
16670:
16665:
16660:
16655:
16650:
16645:
16640:
16635:
16630:
16625:
16620:
16615:
16610:
16605:
16600:
16578:
16573:
16568:
16563:
16558:
16553:
16548:
16546:Chloroindazole
16543:
16538:
16532:
16530:
16526:
16525:
16523:
16522:
16517:
16512:
16507:
16502:
16497:
16492:
16487:
16482:
16477:
16472:
16467:
16465:Spironolactone
16462:
16457:
16452:
16447:
16442:
16437:
16432:
16427:
16422:
16417:
16412:
16407:
16402:
16397:
16392:
16387:
16382:
16377:
16372:
16367:
16362:
16357:
16352:
16347:
16342:
16337:
16332:
16327:
16322:
16317:
16312:
16307:
16302:
16297:
16292:
16287:
16282:
16277:
16272:
16267:
16262:
16257:
16252:
16247:
16242:
16237:
16232:
16227:
16222:
16217:
16212:
16207:
16202:
16196:
16194:
16179:
16178:
16176:
16175:
16166:Others (e.g.,
16164:
16114:
16100:
16086:
16056:
16038:
16016:
15974:
15964:
15942:
15937:
15894:liquiritigenin
15803:
15789:
15767:
15741:Xenoestrogens:
15737:
15736:
15731:
15726:
15721:
15712:
15711:
15706:
15701:
15696:
15691:
15686:
15681:
15676:
15671:
15666:
15661:
15656:
15651:
15646:
15641:
15636:
15631:
15626:
15621:
15616:
15614:Paroxypropione
15611:
15606:
15601:
15596:
15591:
15583:
15575:
15570:
15565:
15564:
15563:
15553:
15548:
15543:
15538:
15533:
15528:
15526:Estrobin (DBE)
15523:
15518:
15513:
15508:
15503:
15498:
15493:
15488:
15483:
15482:
15481:
15471:
15470:
15469:
15459:
15454:
15449:
15444:
15439:
15434:
15429:
15424:
15419:
15417:Allenolic acid
15414:
15409:
15404:
15399:
15394:
15389:
15384:
15375:
15374:
15369:
15364:
15359:
15354:
15349:
15344:
15339:
15334:
15329:
15324:
15322:Norethisterone
15319:
15314:
15312:Mytatrienediol
15309:
15304:
15299:
15294:
15289:
15284:
15279:
15274:
15269:
15264:
15259:
15257:Ethylestradiol
15254:
15252:Ethinylestriol
15249:
15248:
15247:
15242:
15232:
15231:
15230:
15220:
15215:
15214:
15213:
15208:
15203:
15201:Estrone esters
15193:
15188:
15183:
15178:
15177:
15176:
15171:
15169:Estriol esters
15161:
15156:
15154:Estrapronicate
15151:
15146:
15141:
15140:
15139:
15134:
15129:
15119:
15114:
15109:
15104:
15099:
15094:
15089:
15084:
15076:
15071:
15066:
15061:
15056:
15051:
15046:
15045:
15044:
15034:
15029:
15024:
15019:
15014:
15009:
14979:
14974:
14972:Alestramustine
14969:
14964:
14959:
14954:
14949:
14944:
14939:
14934:
14929:
14924:
14919:
14909:
14904:
14899:
14894:
14889:
14884:
14879:
14874:
14872:16-Ketoestrone
14869:
14864:
14859:
14854:
14849:
14844:
14839:
14834:
14829:
14824:
14819:
14814:
14809:
14804:
14799:
14794:
14789:
14784:
14779:
14774:
14769:
14764:
14759:
14754:
14749:
14744:
14739:
14734:
14729:
14720:
14718:
14711:
14700:
14699:
14689:
14688:
14681:
14674:
14666:
14657:
14656:
14654:
14653:
14648:
14643:
14638:
14633:
14628:
14624:
14621:
14620:
14617:
14616:
14614:
14613:
14608:
14598:
14593:
14569:-α-Amino acids
14563:
14558:
14553:
14548:
14517:
14515:
14508:
14502:
14501:
14498:
14497:
14495:
14494:
14489:
14484:
14479:
14474:
14469:
14464:
14459:
14454:
14449:
14444:
14439:
14434:
14429:
14424:
14419:
14414:
14409:
14404:
14399:
14394:
14389:
14384:
14379:
14374:
14369:
14364:
14359:
14354:
14346:
14338:
14330:
14325:
14320:
14315:
14310:
14305:
14300:
14295:
14290:
14285:
14280:
14275:
14270:
14265:
14260:
14255:
14250:
14245:
14240:
14235:
14225:
14220:
14215:
14210:
14205:
14200:
14195:
14190:
14185:
14159:
14154:
14149:
14144:
14139:
14134:
14129:
14124:
14119:
14114:
14109:
14096:
14095:
14090:
14085:
14080:
14075:
14070:
14065:
14063:Spironolactone
14060:
14055:
14050:
14045:
14040:
14035:
14030:
14025:
14020:
14015:
14010:
14005:
14000:
13995:
13990:
13985:
13980:
13975:
13970:
13965:
13960:
13955:
13950:
13945:
13940:
13935:
13930:
13925:
13920:
13915:
13910:
13905:
13900:
13895:
13890:
13888:Cyproheptadine
13885:
13880:
13875:
13870:
13865:
13863:Canrenoic acid
13860:
13855:
13850:
13845:
13840:
13835:
13830:
13825:
13820:
13815:
13806:
13804:
13800:
13799:
13797:
13796:
13791:
13786:
13781:
13772:
13771:
13766:
13761:
13756:
13751:
13746:
13741:
13736:
13731:
13726:
13721:
13716:
13711:
13706:
13701:
13696:
13691:
13686:
13681:
13676:
13671:
13666:
13661:
13656:
13651:
13646:
13641:
13636:
13631:
13626:
13621:
13616:
13611:
13602:
13600:
13589:
13588:
13586:
13585:
13580:
13575:
13570:
13565:
13560:
13555:
13546:
13545:
13540:
13535:
13526:
13525:
13520:
13511:
13510:
13505:
13504:
13503:
13493:
13491:Norgestrienone
13488:
13483:
13469:
13467:Norethisterone
13464:
13463:
13462:
13452:
13442:
13440:Levonorgestrel
13437:
13432:
13427:
13426:
13425:
13415:
13410:
13405:
13396:
13395:
13390:
13385:
13376:
13375:
13370:
13369:
13368:
13358:
13349:
13348:
13339:
13338:
13329:
13328:
13323:
13314:
13313:
13308:
13303:
13298:
13293:
13288:
13283:
13278:
13273:
13268:
13263:
13261:Ethyldienolone
13258:
13253:
13248:
13239:
13238:
13233:
13228:
13223:
13218:
13213:
13208:
13203:
13202:
13201:
13196:
13186:
13181:
13176:
13171:
13166:
13164:Androisoxazole
13157:
13156:
13151:
13146:
13141:
13140:
13139:
13124:
13119:
13118:
13117:
13112:
13107:
13102:
13092:
13087:
13082:
13077:
13072:
13067:
13062:
13057:
13052:
13047:
13042:
13033:
13032:
13027:
13022:
13013:
13012:
13011:
13010:
13005:
12995:
12990:
12989:
12988:
12983:
12978:
12973:
12963:
12962:
12961:
12951:
12946:
12945:
12944:
12934:
12933:
12932:
12922:
12917:
12904:
12903:
12902:
12897:
12892:
12882:
12877:
12872:
12867:
12862:
12861:
12860:
12850:
12845:
12840:
12835:
12834:
12833:
12823:
12814:
12813:
12808:
12807:
12806:
12796:
12791:
12790:
12789:
12779:
12777:Methyldiazinol
12774:
12773:
12772:
12762:
12757:
12752:
12747:
12742:
12741:
12740:
12730:
12729:
12728:
12713:
12708:
12703:
12698:
12697:
12696:
12686:
12681:
12676:
12671:
12666:
12661:
12659:1-Testosterone
12656:
12651:
12646:
12637:
12636:
12635:
12634:
12629:
12614:
12609:
12604:
12599:
12594:
12589:
12588:
12587:
12582:
12572:
12567:
12566:
12565:
12555:
12554:
12553:
12548:
12543:
12533:
12528:
12527:
12526:
12516:
12511:
12506:
12505:
12504:
12499:
12494:
12489:
12479:
12474:
12469:
12464:
12459:
12454:
12449:
12444:
12435:
12433:
12426:
12415:
12414:
12404:
12403:
12396:
12389:
12381:
12375:
12372:
12371:
12359:
12358:
12296:cell signaling
12272:photosynthesis
12270:Violet nodes:
12258:Orange nodes:
12234:
12233:
12229:
12228:
11915:
11861:Aromatic amino
11768:Branched-chain
11318:Light reaction
11009:
11008:
11001:
11000:
10999:
10998:
10993:
10992:
10989:
10988:
10980:
10979:
10972:
10965:
10957:
10948:
10947:
10944:
10943:
10941:
10940:
10935:
10930:
10929:
10928:
10917:
10915:
10911:
10910:
10907:
10906:
10904:
10903:
10898:
10893:
10888:
10883:
10877:
10875:
10871:
10870:
10868:
10867:
10862:
10859:Beta oxidation
10851:
10849:
10840:
10824:
10823:
10820:
10819:
10816:
10815:
10813:
10812:
10807:
10801:
10798:
10797:
10795:
10794:
10789:
10784:
10779:
10777:Chemosynthesis
10774:
10769:
10767:Photosynthesis
10763:
10757:
10753:
10752:
10749:
10748:
10746:
10745:
10744:
10743:
10738:
10727:
10724:
10723:
10721:
10720:
10719:
10718:
10716:Leloir pathway
10708:
10707:
10706:
10704:Polyol pathway
10696:
10690:
10687:
10686:
10684:
10683:
10677:Glycogenolysis
10673:
10670:
10669:
10667:
10666:
10656:
10650:
10643:
10626:
10625:
10622:
10621:
10619:
10618:
10613:
10608:
10603:
10597:
10595:
10587:
10586:
10584:
10583:
10578:
10572:
10566:
10564:
10555:
10554:
10548:
10542:
10540:
10531:
10525:
10524:
10521:
10520:
10518:
10517:
10516:
10515:
10510:
10505:
10490:
10488:
10482:
10481:
10479:
10478:
10474:
10472:
10466:
10465:
10463:
10462:
10433:
10431:
10422:
10414:
10413:
10411:
10410:
10405:
10400:
10394:
10392:
10388:
10387:
10372:
10371:
10364:
10357:
10349:
10340:
10339:
10337:
10336:
10331:
10326:
10321:
10312:
10311:
10306:
10301:
10296:
10284:
10282:
10278:
10277:
10275:
10274:
10272:Estratetraenol
10269:
10264:
10259:
10254:
10252:Androstadienol
10249:
10247:3β-Androstenol
10244:
10242:3α-Androstenol
10232:
10231:
10226:
10221:
10216:
10211:
10206:
10201:
10196:
10191:
10186:
10184:3α-Androstenol
10181:
10172:
10171:
10166:
10161:
10156:
10151:
10146:
10141:
10136:
10131:
10126:
10121:
10116:
10114:Corticosterone
10111:
10106:
10101:
10096:
10091:
10086:
10077:
10076:
10071:
10058:
10056:
10050:
10049:
10046:
10045:
10043:
10042:
10037:
10032:
10027:
10018:
10017:
10012:
10007:
10002:
9997:
9992:
9987:
9982:
9976:
9974:
9968:
9967:
9965:
9964:
9950:
9945:
9940:
9935:
9930:
9925:
9920:
9915:
9910:
9905:
9900:
9895:
9890:
9885:
9876:
9875:
9870:
9865:
9860:
9855:
9850:
9845:
9840:
9835:
9830:
9821:
9820:
9818:16-Ketoestrone
9815:
9810:
9805:
9800:
9795:
9790:
9785:
9780:
9775:
9770:
9765:
9760:
9755:
9750:
9745:
9740:
9735:
9730:
9725:
9716:
9714:
9708:
9707:
9705:
9704:
9699:
9694:
9689:
9684:
9679:
9674:
9669:
9664:
9659:
9654:
9649:
9644:
9639:
9634:
9629:
9624:
9619:
9610:
9609:
9604:
9599:
9594:
9589:
9584:
9579:
9574:
9569:
9564:
9559:
9554:
9549:
9547:Androstenediol
9544:
9539:
9534:
9529:
9524:
9518:
9516:
9507:
9501:
9500:
9497:
9496:
9494:
9493:
9488:
9486:Corticosterone
9483:
9478:
9473:
9468:
9463:
9458:
9453:
9448:
9443:
9437:
9435:
9429:
9428:
9426:
9425:
9420:
9411:
9410:
9405:
9400:
9395:
9390:
9385:
9380:
9378:Corticosterone
9375:
9370:
9365:
9360:
9355:
9350:
9345:
9339:
9337:
9328:
9322:
9321:
9319:
9318:
9313:
9308:
9303:
9298:
9293:
9288:
9279:
9270:
9264:
9262:
9256:
9255:
9245:
9244:
9237:
9230:
9222:
9213:
9212:
9209:
9208:
9206:
9205:
9203:Ergocalciferol
9200:
9195:
9190:
9188:Ergostatrienol
9185:
9180:
9174:
9172:
9170:Ergocalciferol
9165:
9164:
9162:
9161:
9150:
9145:
9140:
9135:
9130:
9125:
9123:Cycloeucalenol
9120:
9114:
9112:
9102:
9098:
9097:
9095:
9094:
9087:
9078:
9068:
9066:
9054:
9053:
9051:
9050:
9045:
9040:
9035:
9030:
9024:
9023:
9018:
9013:
9008:
9003:
8997:
8996:
8991:
8986:
8981:
8976:
8970:
8969:
8964:
8959:
8954:
8948:
8946:
8939:
8938:
8935:
8934:
8932:
8931:
8926:
8921:
8916:
8911:
8906:
8901:
8896:
8890:
8884:
8878:
8877:
8874:
8873:
8871:
8870:
8865:
8859:
8857:
8851:
8850:
8848:
8847:
8842:
8836:
8834:
8830:
8829:
8827:
8826:
8821:
8816:
8811:
8806:
8804:Mevalonic acid
8800:
8798:
8791:
8790:
8788:
8787:
8782:
8777:
8771:
8769:
8763:
8762:
8760:
8759:
8754:
8749:
8744:
8739:
8733:
8731:
8721:
8715:
8714:
8700:
8699:
8692:
8685:
8677:
8668:
8667:
8665:
8664:
8658:
8651:
8649:
8645:
8644:
8642:
8641:
8638:protein domain
8629:
8627:
8623:
8622:
8620:
8619:
8616:
8612:
8610:
8606:
8605:
8603:
8602:
8599:
8594:
8592:Natural rubber
8588:
8586:
8583:Polyterpenoids
8579:
8578:
8575:
8574:
8572:
8571:
8566:
8561:
8556:
8551:
8546:
8540:
8538:
8531:
8530:
8528:
8527:
8522:
8517:
8512:
8507:
8505:Delta-Carotene
8502:
8500:Gamma-Carotene
8497:
8492:
8490:Alpha-Carotene
8486:
8484:
8475:
8463:
8462:
8460:
8459:
8456:
8452:
8450:
8446:
8445:
8442:
8441:
8439:
8438:
8437:
8436:
8431:
8429:Betulinic acid
8426:
8421:
8419:Oleanolic acid
8413:
8408:
8405:
8400:
8395:
8389:
8387:
8383:
8382:
8380:
8379:
8374:
8369:
8364:
8359:
8354:
8353:
8352:
8347:
8342:
8337:
8332:
8331:Citrostadienol
8329:
8318:
8316:
8307:
8300:
8299:
8297:
8296:
8292:
8290:
8283:
8282:
8279:
8278:
8276:
8275:
8274:Palustric acid
8272:
8269:
8266:
8261:
8258:
8255:
8250:
8247:
8242:
8239:
8236:
8230:
8228:
8222:
8221:
8219:
8218:
8213:
8208:
8202:
8200:
8196:
8195:
8193:
8192:
8189:
8186:
8183:
8178:
8172:
8170:
8166:
8165:
8163:
8162:
8157:
8154:
8147:
8145:
8141:
8140:
8138:
8137:
8132:
8126:
8124:
8120:
8119:
8117:
8116:
8113:
8108:
8102:
8100:
8093:
8086:
8085:
8083:
8082:
8079:
8076:
8071:
8068:
8063:
8060:
8055:
8050:
8045:
8040:
8034:
8032:
8025:
8024:
8021:
8020:
8018:
8017:
8012:
8007:
8002:
8000:Bornyl acetate
7997:
7992:
7986:
7984:
7980:
7979:
7977:
7976:
7971:
7966:
7961:
7951:
7946:
7941:
7935:
7933:
7929:
7928:
7926:
7925:
7920:
7915:
7910:
7905:
7900:
7895:
7889:
7887:
7880:
7874:
7873:
7870:
7869:
7867:
7866:
7861:
7856:
7851:
7846:
7831:
7829:
7825:
7824:
7822:
7821:
7816:
7811:
7805:
7803:
7799:
7798:
7796:
7795:
7790:
7784:
7782:
7775:
7771:
7767:
7759:
7758:
7756:
7755:
7750:
7745:
7741:
7737:
7730:
7728:
7725:Hemiterpenoids
7721:
7720:
7718:
7717:
7711:
7708:
7702:
7699:
7696:
7684:
7682:
7678:
7677:
7660:
7659:
7652:
7645:
7637:
7628:
7627:
7625:
7624:
7618:
7616:
7612:
7611:
7609:
7608:
7603:
7597:
7595:
7591:
7590:
7588:
7587:
7582:
7580:Hydroxysteroid
7577:
7575:17-Ketosteroid
7571:
7569:
7563:
7562:
7560:
7559:
7553:
7551:
7548:
7544:
7543:
7541:
7540:
7535:
7529:
7527:
7524:
7520:
7519:
7517:
7516:
7510:
7508:
7505:
7501:
7500:
7498:
7497:
7492:
7487:
7482:
7477:
7472:
7467:
7455:
7450:
7437:
7435:
7432:
7428:
7427:
7425:
7424:
7422:19-Norpregnane
7418:
7416:
7413:
7409:
7408:
7406:
7405:
7396:
7394:Androstadienol
7391:
7389:Androstenolone
7386:
7384:Androstanolone
7381:
7376:
7371:
7366:
7364:Androstenediol
7361:
7359:Androstanediol
7356:
7351:
7346:
7341:
7332:Androstatriene
7329:
7324:
7311:
7309:
7306:
7302:
7301:
7299:
7298:
7293:
7288:
7276:
7271:
7258:
7256:
7253:
7249:
7248:
7246:
7245:
7239:
7237:
7234:
7230:
7229:
7227:classification
7221:
7220:
7213:
7206:
7198:
7191:
7190:
7173:
7167:
7146:
7108:
7060:
7053:
7032:
7012:
7006:
6992:
6990:
6987:
6984:
6983:
6957:
6931:
6905:
6879:
6853:
6827:
6801:
6774:
6759:
6733:
6706:
6699:
6668:
6657:(7): 398–404.
6634:
6577:
6570:
6548:
6515:
6484:
6463:(5): 687–702.
6443:
6408:
6373:
6322:
6287:
6259:
6252:
6222:
6196:
6161:
6115:
6076:(8): 779–804.
6056:
6015:
5972:
5921:
5878:
5840:
5783:
5745:
5686:
5637:
5608:(2): 358–369.
5602:Int. J. Cancer
5585:
5578:
5560:
5545:
5527:
5494:
5479:
5449:
5414:(5): 210–230.
5394:
5368:
5333:
5298:
5268:
5261:
5243:
5217:
5176:
5169:
5151:
5144:
5126:
5093:Phytochemistry
5083:
5076:
5045:
5038:
5020:
4963:
4914:
4870:
4819:
4783:
4732:
4702:
4674:
4635:
4600:
4590:
4564:
4521:
4492:(5): 284–296.
4472:
4441:(7): bvac037.
4421:
4410:(4): 391–416.
4394:
4367:(3): 428–429.
4351:
4340:(2): 333–360.
4324:
4298:
4272:
4208:
4197:
4171:
4129:
4091:
4084:. p. 66:
4080:
4054:
4028:
4017:
3991:
3952:
3898:
3856:
3817:
3746:
3734:
3727:
3705:
3694:
3672:
3658:
3637:
3586:
3560:
3532:
3505:(8 May 1815).
3494:
3463:
3430:
3387:
3380:
3357:
3239:
3238:
3236:
3233:
3231:
3230:
3225:
3220:
3215:
3210:
3205:
3200:
3195:
3190:
3185:
3179:
3177:
3174:
3173:
3172:
3166:mevalonic acid
3158:
3147:
3133:
3111:
3097:
3090:
3070:
3067:
3043:petrochemicals
3034:
3031:
2988:
2985:
2983:
2980:
2964:contraceptives
2936:
2933:
2903:chromatography
2878:
2875:
2826:
2823:
2771:
2768:
2765:
2764:
2744:secretion rate
2732:
2729:
2728:
2725:
2724:
2721:
2718:
2715:
2712:
2709:
2705:
2704:
2703:0.1–0.9 ng/mL
2701:
2698:
2695:
2692:
2689:
2686:
2680:
2679:
2676:
2673:
2670:
2669:Insignificant
2667:
2664:
2660:
2659:
2656:
2653:
2650:
2649:Insignificant
2647:
2644:
2641:
2635:
2634:
2631:
2628:
2625:
2624:Insignificant
2622:
2619:
2618:Postmenopause
2615:
2614:
2613:190–341 pg/mL
2611:
2608:
2605:
2602:
2599:
2595:
2594:
2591:
2588:
2585:
2582:
2579:
2576:
2570:
2569:
2566:
2565:22–230 pmol/L
2563:
2560:
2559:Insignificant
2557:
2554:
2553:Postmenopause
2550:
2549:
2546:
2543:
2540:
2537:
2534:
2530:
2529:
2526:
2523:
2520:
2517:
2514:
2511:
2505:
2504:
2501:
2498:
2495:
2492:
2489:
2486:
2484:
2478:
2477:
2474:
2471:
2468:
2465:
2462:
2459:
2457:
2452:
2448:
2447:
2446:200–900 pg/mL
2444:
2441:
2438:
2437:Insignificant
2435:
2432:
2429:
2427:
2421:
2420:
2417:
2414:
2411:
2408:
2405:
2402:
2400:
2394:
2393:
2390:
2389:37–250 pmol/L
2387:
2384:
2381:
2378:
2375:
2373:
2367:
2366:
2363:
2360:
2357:
2354:
2351:
2348:
2346:
2340:
2339:
2336:
2333:
2330:
2327:
2324:
2321:
2319:
2314:
2310:
2309:
2302:
2295:
2294:
2291:
2286:
2281:
2276:
2271:
2268:
2260:
2259:
2252:
2245:
2237:
2234:
2233:
2208:
2198:
2195:
2172:
2169:adrenal cortex
2165:corticosterone
2161:
2140:(corticoids),
2107:
2102:
2026:and ends with
2016:Main article:
2005:
2002:
1930:are made from
1895:
1892:
1873:cell membranes
1860:
1857:
1792:biomimetically
1764:
1745:
1742:
1731:17-ketosteroid
1726:
1722:
1718:
1713:
1712:
1709:
1706:
1700:
1699:
1696:
1693:
1687:
1686:
1683:
1680:
1674:
1673:
1670:
1667:
1661:
1660:
1657:
1654:
1648:
1647:
1644:
1641:
1614:
1595:
1594:
1574:
1572:
1565:
1559:
1556:
1554:
1551:
1550:
1549:
1539:ergocalciferol
1537:forms such as
1524:
1523:
1509:
1505:, and various
1495:
1486:
1477:
1465:
1456:
1434:
1433:
1432:
1431:
1430:
1429:
1417:
1416:
1415:
1400:
1399:
1398:
1369:
1368:
1367:
1366:
1365:
1362:blood pressure
1345:
1344:
1343:
1337:glucocorticoid
1308:
1307:
1287:
1285:
1278:
1272:
1269:
1267:
1264:
1263:
1262:
1252:
1218:
1180:cell membranes
1176:cell membranes
1151:
1148:
1115:
1112:
1033:amphotericin B
1020:
1017:
991:eukaryogenesis
976:
975:
948:
946:
939:
933:
930:
912:
911:
886:
884:
877:
871:
868:
816:androstenediol
726:R/S convention
722:chiral centers
665:
662:
659:
658:
656:
642:
599:hydroxyl group
593:For instance,
591:
590:
583:
580:
577:
557:
556:
546:
539:
537:
531:
524:
522:
516:
509:
507:
493:
486:
484:
480:corticosteroid
478:, a synthetic
474:
467:
465:
455:, showing the
447:
440:
438:
425:
418:
415:
398:derivative of
340:
337:
335:
332:
302:
301:
296:
289:
288:
284:
277:
276:
275:
274:
273:
267:
244:of the rings.
218:core structure
116:cell membranes
58:
36:
30:
27:
25:
9:
6:
4:
3:
2:
20893:
20882:
20879:
20877:
20874:
20873:
20871:
20850:
20847:
20845:
20842:
20840:
20837:
20835:
20832:
20830:
20827:
20824:
20823:
20820:
20810:
20807:
20806:
20804:
20800:
20794:
20791:
20789:
20786:
20784:
20781:
20779:
20776:
20774:
20771:
20769:
20766:
20764:
20761:
20759:
20756:
20754:
20751:
20750:
20748:
20744:
20741:
20735:
20725:
20719:
20709:
20706:
20704:
20701:
20699:
20698:Valproic acid
20696:
20694:
20691:
20689:
20686:
20684:
20681:
20679:
20676:
20674:
20671:
20669:
20666:
20665:Nonsteroidal:
20663:
20662:
20659:
20656:
20654:
20651:
20649:
20646:
20644:
20641:
20639:
20636:
20634:
20631:
20629:
20626:
20624:
20621:
20619:
20616:
20614:
20611:
20608:
20607:
20605:
20601:
20595:
20594:Syringic acid
20592:
20590:
20587:
20585:
20582:
20580:
20577:
20575:
20572:
20570:
20567:
20566:Nonsteroidal:
20564:
20563:
20560:
20557:
20555:
20552:
20550:
20547:
20545:
20542:
20540:
20537:
20535:
20532:
20530:
20527:
20525:
20522:
20520:
20517:
20515:
20512:
20510:
20507:
20505:
20502:
20500:
20497:
20495:
20494:Guggulsterone
20492:
20490:
20487:
20485:
20482:
20480:
20477:
20475:
20472:
20470:
20467:
20464:
20463:
20461:
20455:
20446:
20440:
20437:
20435:
20432:
20429:
20428:
20425:
20422:
20420:
20417:
20415:
20412:
20410:
20407:
20405:
20402:
20400:
20399:Riligustilide
20397:
20395:
20392:
20390:
20387:
20385:
20382:
20381:Nonsteroidal:
20379:
20378:
20375:
20372:
20370:
20367:
20365:
20362:
20360:
20357:
20355:
20352:
20350:
20347:
20345:
20342:
20340:
20337:
20335:
20332:
20330:
20327:
20324:
20323:
20320:
20317:
20315:
20312:
20310:
20307:
20304:
20300:
20296:
20293:
20291:
20288:
20286:
20283:
20281:
20278:
20276:
20273:
20271:
20268:
20265:
20261:
20257:
20254:
20252:
20249:
20247:
20244:
20242:
20239:
20237:
20234:
20232:
20229:
20227:
20224:
20222:
20219:
20217:
20214:
20212:
20209:
20207:
20204:
20202:
20199:
20197:
20194:
20192:
20189:
20187:
20184:
20182:
20179:
20177:
20174:
20172:
20169:
20167:
20164:
20162:
20159:
20157:
20154:
20152:
20149:
20147:
20144:
20142:
20139:
20137:
20133:
20130:
20128:
20125:
20123:
20120:
20118:
20115:
20113:
20110:
20108:
20105:
20103:
20100:
20098:
20095:
20093:
20090:
20088:
20085:
20083:
20080:
20078:
20075:
20072:
20068:
20064:
20061:
20059:
20056:
20054:
20051:
20049:
20046:
20044:
20041:
20039:
20036:
20034:
20031:
20028:
20024:
20021:
20019:
20016:
20014:
20011:
20009:
20006:
20004:
20001:
19999:
19996:
19994:
19991:
19989:
19986:
19984:
19981:
19977:
19976:Ethandrostate
19974:
19973:
19972:
19969:
19967:
19964:
19962:
19959:
19957:
19954:
19952:
19949:
19947:
19944:
19942:
19939:
19937:
19936:Allylestrenol
19934:
19932:
19929:
19927:
19924:
19922:
19918:
19915:
19914:
19911:
19908:
19906:
19903:
19901:
19898:
19896:
19893:
19891:
19888:
19886:
19883:
19881:
19878:
19876:
19873:
19871:
19868:
19866:
19863:
19861:
19858:
19856:
19853:
19851:
19848:
19846:
19843:
19841:
19838:
19836:
19833:
19831:
19828:
19826:
19823:
19821:
19818:
19816:
19813:
19811:
19808:
19806:
19803:
19801:
19798:
19795:
19794:
19791:
19788:
19786:
19783:
19781:
19778:
19776:
19773:
19771:
19770:Pentagestrone
19768:
19766:
19763:
19761:
19758:
19756:
19753:
19751:
19748:
19746:
19743:
19741:
19738:
19736:
19733:
19731:
19728:
19726:
19723:
19721:
19718:
19716:
19713:
19711:
19708:
19706:
19703:
19701:
19698:
19696:
19693:
19691:
19688:
19686:
19683:
19681:
19678:
19676:
19673:
19671:
19668:
19666:
19663:
19661:
19658:
19656:
19655:Hydromadinone
19653:
19651:
19648:
19646:
19645:Gestobutanoyl
19643:
19641:
19638:
19636:
19633:
19631:
19628:
19626:
19623:
19621:
19618:
19616:
19613:
19611:
19608:
19606:
19603:
19601:
19598:
19596:
19593:
19591:
19588:
19586:
19583:
19581:
19578:
19576:
19573:
19571:
19568:
19566:
19563:
19561:
19558:
19556:
19553:
19551:
19548:
19546:
19543:
19541:
19538:
19536:
19533:
19531:
19528:
19526:
19525:Chlormadinone
19523:
19521:
19518:
19516:
19513:
19511:
19508:
19506:
19503:
19501:
19498:
19496:
19493:
19491:
19488:
19486:
19483:
19481:
19478:
19476:
19473:
19471:
19468:
19466:
19463:
19461:
19458:
19456:
19453:
19451:
19448:
19445:
19444:
19441:
19438:
19436:
19433:
19431:
19428:
19426:
19423:
19421:
19418:
19416:
19413:
19411:
19408:
19406:
19403:
19400:
19399:
19396:
19393:
19391:
19388:
19386:
19383:
19381:
19378:
19376:
19373:
19371:
19368:
19366:
19363:
19361:
19358:
19356:
19353:
19351:
19348:
19346:
19343:
19341:
19338:
19336:
19333:
19331:
19328:
19326:
19323:
19321:
19318:
19315:
19314:
19312:
19308:
19305:
19300:
19294:
19290:
19287:
19280:
19275:
19273:
19268:
19266:
19261:
19260:
19257:
19245:
19242:
19240:
19237:
19235:
19232:
19230:
19227:
19224:
19223:
19220:
19210:
19207:
19205:
19202:
19200:
19197:
19195:
19192:
19190:
19187:
19185:
19182:
19180:
19177:
19175:
19172:
19170:
19167:
19165:
19162:
19160:
19157:
19155:
19152:
19150:
19147:
19145:
19142:
19141:Nonsteroidal:
19139:
19138:
19135:
19132:
19130:
19127:
19125:
19122:
19120:
19117:
19115:
19112:
19110:
19107:
19105:
19102:
19100:
19097:
19095:
19092:
19090:
19087:
19085:
19082:
19080:
19077:
19075:
19072:
19070:
19067:
19065:
19062:
19060:
19057:
19055:
19052:
19050:
19047:
19045:
19042:
19040:
19037:
19035:
19032:
19030:
19027:
19025:
19022:
19020:
19017:
19015:
19012:
19010:
19007:
19005:
19002:
19000:
18997:
18995:
18992:
18990:
18989:Guggulsterone
18987:
18985:
18982:
18980:
18977:
18975:
18972:
18970:
18967:
18965:
18962:
18960:
18957:
18955:
18952:
18950:
18947:
18945:
18942:
18940:
18937:
18935:
18932:
18930:
18927:
18925:
18922:
18920:
18917:
18915:
18912:
18910:
18907:
18905:
18902:
18900:
18897:
18894:
18893:
18891:
18887:
18879:
18876:
18875:
18874:
18871:
18867:
18864:
18862:
18859:
18857:
18856:Prednimustine
18854:
18852:
18849:
18847:
18844:
18842:
18839:
18838:
18837:
18834:
18830:
18827:
18826:
18825:
18822:
18818:
18815:
18814:
18813:
18810:
18806:
18803:
18802:
18801:
18798:
18794:
18791:
18789:
18786:
18784:
18781:
18780:
18778:
18774:
18771:
18767:
18764:
18762:
18759:
18758:
18757:
18754:
18752:
18749:
18747:
18744:
18742:
18739:
18737:
18734:
18732:
18729:
18727:
18724:
18720:
18717:
18715:
18712:
18711:
18710:
18707:
18703:
18700:
18699:
18698:
18695:
18691:
18688:
18687:
18686:
18683:
18682:
18680:
18676:
18673:
18668:
18662:
18658:
18655:
18648:
18643:
18641:
18636:
18634:
18629:
18628:
18625:
18613:
18610:
18608:
18605:
18603:
18600:
18598:
18595:
18592:
18591:
18588:
18578:
18577:(ISIS-426115)
18571:
18568:
18567:
18565:
18561:
18555:
18552:
18550:
18547:
18545:
18542:
18540:
18537:
18535:
18532:
18530:
18527:
18525:
18522:
18520:
18517:
18515:
18512:
18510:
18507:
18505:
18502:
18500:
18497:
18495:
18492:
18490:
18487:
18485:
18482:
18480:
18477:
18475:
18472:
18470:
18467:
18465:
18462:
18460:
18457:
18455:
18454:Guggulsterone
18452:
18450:
18447:
18445:
18442:
18440:
18437:
18435:
18432:
18430:
18427:
18425:
18422:
18420:
18417:
18415:
18412:
18410:
18407:
18405:
18402:
18400:
18397:
18396:
18394:
18392:
18388:
18382:
18379:
18377:
18376:Fosdagrocorat
18374:
18372:
18369:
18368:
18366:
18360:
18351:
18345:
18342:
18340:
18337:
18334:
18333:
18330:
18327:
18325:
18322:
18320:
18317:
18315:
18312:
18310:
18307:
18305:
18302:
18300:
18297:
18295:
18292:
18290:
18287:
18285:
18282:
18280:
18277:
18275:
18272:
18270:
18267:
18265:
18262:
18260:
18257:
18255:
18252:
18250:
18247:
18245:
18242:
18240:
18237:
18235:
18232:
18230:
18227:
18225:
18222:
18220:
18217:
18215:
18212:
18210:
18207:
18205:
18202:
18200:
18197:
18195:
18192:
18189:
18188:
18185:
18182:
18180:
18177:
18175:
18172:
18170:
18167:
18163:
18160:
18159:
18158:
18157:Nicocortonide
18155:
18153:
18150:
18148:
18145:
18143:
18140:
18138:
18135:
18132:
18131:
18128:
18125:
18123:
18120:
18116:
18113:
18111:
18108:
18107:
18106:
18103:
18101:
18098:
18094:
18091:
18090:
18089:
18086:
18084:
18081:
18079:
18076:
18074:
18071:
18067:
18064:
18062:
18059:
18057:
18054:
18053:
18052:
18049:
18045:
18042:
18041:
18040:
18037:
18035:
18032:
18030:
18027:
18025:
18022:
18020:
18017:
18013:
18010:
18009:
18008:
18005:
18003:
18002:Dexbudesonide
18000:
17996:
17993:
17991:
17988:
17987:
17986:
17983:
17981:
17978:
17976:
17973:
17971:
17968:
17966:
17963:
17961:
17958:
17956:
17953:
17951:
17948:
17946:
17943:
17941:
17938:
17935:
17934:
17931:
17928:
17924:
17921:
17920:
17919:
17916:
17912:
17909:
17908:
17907:
17906:Triamcinolone
17904:
17900:
17897:
17896:
17895:
17892:
17888:
17885:
17884:
17883:
17880:
17878:
17875:
17871:
17868:
17867:
17866:
17863:
17859:
17856:
17854:
17851:
17849:
17846:
17845:
17844:
17843:Paramethasone
17841:
17837:
17834:
17833:
17832:
17829:
17825:
17822:
17820:
17817:
17816:
17815:
17812:
17808:
17805:
17804:
17803:
17800:
17796:
17793:
17792:
17791:
17788:
17786:
17785:Isoprednidene
17783:
17779:
17776:
17775:
17774:
17771:
17769:
17766:
17764:
17763:Halocortolone
17761:
17757:
17754:
17752:
17749:
17748:
17746:
17742:
17739:
17738:
17737:
17734:
17730:
17727:
17726:
17725:
17724:Fluocortolone
17722:
17718:
17715:
17714:
17713:
17710:
17708:
17705:
17701:
17698:
17696:
17693:
17692:
17691:
17688:
17686:
17683:
17681:
17678:
17674:
17671:
17670:
17669:
17666:
17662:
17659:
17657:
17654:
17653:
17652:
17649:
17645:
17642:
17641:
17640:
17637:
17633:
17630:
17629:
17628:
17625:
17623:
17620:
17618:
17615:
17611:
17608:
17607:
17606:
17603:
17599:
17596:
17595:
17594:
17591:
17587:
17584:
17583:
17582:
17579:
17575:
17572:
17571:
17570:
17567:
17563:
17560:
17559:
17558:
17555:
17553:
17550:
17546:
17543:
17541:
17538:
17537:
17536:
17533:
17529:
17526:
17525:
17524:
17521:
17519:
17518:Amelometasone
17516:
17512:
17509:
17508:
17507:
17506:Alclometasone
17504:
17502:
17499:
17496:
17495:
17490:
17487:
17483:
17480:
17479:
17478:
17475:
17474:
17473:
17470:
17468:
17465:
17463:
17460:
17456:
17453:
17451:
17448:
17447:
17446:
17443:
17439:
17436:
17435:
17434:
17431:
17427:
17424:
17422:
17419:
17417:
17416:Prednimustine
17414:
17412:
17409:
17407:
17404:
17402:
17399:
17398:
17397:
17394:
17390:
17387:
17386:
17385:
17382:
17378:
17375:
17374:
17373:
17370:
17368:
17365:
17363:
17360:
17358:
17355:
17351:
17348:
17347:
17346:
17343:
17339:
17336:
17335:
17334:
17331:
17327:
17324:
17323:
17322:
17319:
17315:
17312:
17311:
17310:
17307:
17303:
17300:
17299:
17298:
17295:
17291:
17288:
17287:
17286:
17283:
17279:
17276:
17275:
17274:
17271:
17269:
17266:
17264:
17263:Difluprednate
17261:
17257:
17254:
17252:
17249:
17248:
17247:
17244:
17240:
17237:
17236:
17235:
17232:
17228:
17225:
17224:
17223:
17220:
17216:
17213:
17211:
17208:
17206:
17203:
17202:
17200:
17196:
17193:
17189:
17186:
17184:
17181:
17180:
17179:
17176:
17172:
17169:
17168:
17167:
17164:
17160:
17157:
17156:
17155:
17152:
17150:
17147:
17143:
17140:
17139:
17138:
17135:
17133:
17130:
17126:
17123:
17121:
17118:
17117:
17116:
17113:
17109:
17106:
17105:
17104:
17101:
17097:
17094:
17093:
17092:
17089:
17087:
17084:
17082:
17079:
17077:
17074:
17071:
17070:
17068:
17066:
17062:
17059:
17054:
17048:
17044:
17041:
17034:
17029:
17027:
17022:
17020:
17015:
17014:
17011:
16999:
16996:
16994:
16991:
16989:
16986:
16984:
16981:
16979:
16976:
16973:
16972:
16969:
16959:
16956:
16954:
16951:
16950:
16948:
16944:
16938:
16935:
16933:
16930:
16928:
16925:
16923:
16920:
16918:
16915:
16914:
16912:
16908:
16902:
16899:
16897:
16894:
16892:
16889:
16887:
16884:
16882:
16879:
16877:
16874:
16872:
16869:
16866:
16862:
16859:
16857:
16854:
16852:
16849:
16847:
16844:
16842:
16839:
16837:
16834:
16832:
16829:
16827:
16824:
16822:
16819:
16817:
16814:
16812:
16809:
16807:
16804:
16802:
16799:
16797:
16794:
16792:
16789:
16787:
16784:
16781:
16777:
16773:
16770:
16768:
16765:
16763:
16760:
16758:
16755:
16753:
16750:
16748:
16745:
16743:
16740:
16738:
16735:
16734:
16732:
16728:
16725:
16720:
16714:
16704:
16701:
16698:
16697:
16694:
16691:
16688:
16687:
16684:
16681:
16679:
16676:
16674:
16671:
16669:
16666:
16664:
16661:
16659:
16656:
16654:
16651:
16649:
16646:
16644:
16641:
16639:
16636:
16634:
16631:
16629:
16626:
16624:
16621:
16619:
16616:
16614:
16611:
16609:
16606:
16604:
16601:
16598:
16594:
16590:
16586:
16582:
16579:
16577:
16574:
16572:
16569:
16567:
16564:
16562:
16559:
16557:
16554:
16552:
16549:
16547:
16544:
16542:
16539:
16537:
16534:
16533:
16531:
16527:
16521:
16518:
16516:
16513:
16511:
16508:
16506:
16503:
16501:
16498:
16496:
16493:
16491:
16488:
16486:
16483:
16481:
16478:
16476:
16473:
16471:
16468:
16466:
16463:
16461:
16458:
16456:
16453:
16451:
16448:
16446:
16445:Pipendoxifene
16443:
16441:
16438:
16436:
16433:
16431:
16428:
16426:
16423:
16421:
16418:
16416:
16413:
16411:
16408:
16406:
16403:
16401:
16398:
16396:
16393:
16391:
16388:
16386:
16383:
16381:
16378:
16376:
16373:
16371:
16368:
16366:
16363:
16361:
16358:
16356:
16353:
16351:
16348:
16346:
16343:
16341:
16338:
16336:
16333:
16331:
16328:
16326:
16323:
16321:
16318:
16316:
16313:
16311:
16308:
16306:
16303:
16301:
16298:
16296:
16293:
16291:
16288:
16286:
16283:
16281:
16280:Clomifenoxide
16278:
16276:
16273:
16271:
16268:
16266:
16263:
16261:
16258:
16256:
16255:Brilanestrant
16253:
16251:
16248:
16246:
16243:
16241:
16238:
16236:
16233:
16231:
16228:
16226:
16223:
16221:
16218:
16216:
16213:
16211:
16208:
16206:
16203:
16201:
16198:
16197:
16195:
16189:
16180:
16173:
16169:
16165:
16162:
16158:
16154:
16150:
16146:
16142:
16138:
16134:
16130:
16126:
16122:
16118:
16115:
16112:
16108:
16104:
16101:
16098:
16094:
16091:-like (e.g.,
16090:
16087:
16084:
16080:
16076:
16072:
16068:
16064:
16060:
16057:
16054:
16050:
16046:
16042:
16039:
16036:
16035:guggulsterone
16032:
16028:
16024:
16020:
16019:Phytosteroids
16017:
16014:
16010:
16006:
16002:
15998:
15994:
15990:
15986:
15982:
15978:
15975:
15972:
15968:
15965:
15962:
15960:
15954:
15953:enterolactone
15950:
15946:
15943:
15941:
15938:
15935:
15931:
15927:
15923:
15919:
15915:
15911:
15907:
15903:
15899:
15895:
15891:
15887:
15883:
15879:
15875:
15871:
15867:
15863:
15859:
15855:
15851:
15847:
15843:
15839:
15835:
15831:
15827:
15823:
15819:
15815:
15811:
15807:
15804:
15801:
15797:
15793:
15790:
15787:
15786:wedelolactone
15783:
15779:
15775:
15771:
15768:
15765:
15764:photoanethole
15761:
15757:
15753:
15749:
15745:
15742:
15739:
15738:
15735:
15732:
15730:
15727:
15725:
15722:
15720:
15717:
15714:
15713:
15710:
15707:
15705:
15702:
15700:
15697:
15695:
15692:
15690:
15687:
15685:
15682:
15680:
15677:
15675:
15672:
15670:
15667:
15665:
15662:
15660:
15657:
15655:
15652:
15650:
15647:
15645:
15642:
15640:
15637:
15635:
15632:
15630:
15627:
15625:
15622:
15620:
15619:Pentafluranol
15617:
15615:
15612:
15610:
15607:
15605:
15602:
15600:
15597:
15595:
15592:
15590:
15588:
15584:
15582:
15580:
15576:
15574:
15571:
15569:
15566:
15562:
15559:
15558:
15557:
15554:
15552:
15549:
15547:
15544:
15542:
15539:
15537:
15534:
15532:
15529:
15527:
15524:
15522:
15519:
15517:
15514:
15512:
15509:
15507:
15504:
15502:
15499:
15497:
15494:
15492:
15489:
15487:
15484:
15480:
15477:
15476:
15475:
15472:
15468:
15465:
15464:
15463:
15460:
15458:
15455:
15453:
15450:
15448:
15445:
15443:
15440:
15438:
15435:
15433:
15430:
15428:
15425:
15423:
15420:
15418:
15415:
15413:
15410:
15408:
15405:
15403:
15400:
15398:
15395:
15393:
15390:
15388:
15385:
15383:
15380:
15379:Nonsteroidal:
15377:
15376:
15373:
15370:
15368:
15365:
15363:
15360:
15358:
15355:
15353:
15350:
15348:
15345:
15343:
15340:
15338:
15335:
15333:
15330:
15328:
15325:
15323:
15320:
15318:
15315:
15313:
15310:
15308:
15305:
15303:
15300:
15298:
15295:
15293:
15290:
15288:
15285:
15283:
15280:
15278:
15275:
15273:
15270:
15268:
15265:
15263:
15260:
15258:
15255:
15253:
15250:
15246:
15243:
15241:
15238:
15237:
15236:
15233:
15229:
15228:Ethandrostate
15226:
15225:
15224:
15221:
15219:
15216:
15212:
15209:
15207:
15204:
15202:
15199:
15198:
15197:
15194:
15192:
15189:
15187:
15184:
15182:
15179:
15175:
15172:
15170:
15167:
15166:
15165:
15162:
15160:
15157:
15155:
15152:
15150:
15147:
15145:
15142:
15138:
15135:
15133:
15130:
15128:
15125:
15124:
15123:
15120:
15118:
15115:
15113:
15110:
15108:
15105:
15103:
15100:
15098:
15095:
15093:
15090:
15088:
15085:
15083:
15081:
15077:
15075:
15072:
15070:
15067:
15065:
15062:
15060:
15057:
15055:
15052:
15050:
15047:
15043:
15040:
15039:
15038:
15037:Cloxestradiol
15035:
15033:
15030:
15028:
15025:
15023:
15020:
15018:
15015:
15013:
15010:
15007:
15003:
14999:
14995:
14991:
14987:
14983:
14980:
14978:
14975:
14973:
14970:
14968:
14965:
14963:
14960:
14958:
14955:
14953:
14950:
14948:
14945:
14943:
14940:
14938:
14935:
14933:
14930:
14928:
14925:
14923:
14920:
14917:
14913:
14912:17α-Estradiol
14910:
14908:
14905:
14903:
14900:
14898:
14895:
14893:
14890:
14888:
14885:
14883:
14880:
14878:
14875:
14873:
14870:
14868:
14865:
14863:
14860:
14858:
14855:
14853:
14850:
14848:
14845:
14843:
14840:
14838:
14835:
14833:
14830:
14828:
14825:
14823:
14820:
14818:
14815:
14813:
14810:
14808:
14805:
14803:
14800:
14798:
14795:
14793:
14790:
14788:
14785:
14783:
14780:
14778:
14775:
14773:
14770:
14768:
14765:
14763:
14760:
14758:
14755:
14753:
14750:
14748:
14745:
14743:
14740:
14738:
14735:
14733:
14730:
14728:
14725:
14722:
14721:
14719:
14715:
14712:
14707:
14701:
14697:
14694:
14687:
14682:
14680:
14675:
14673:
14668:
14667:
14664:
14652:
14649:
14647:
14644:
14642:
14639:
14637:
14634:
14632:
14629:
14626:
14625:
14622:
14612:
14609:
14604:
14599:
14597:
14594:
14591:
14584:
14577:
14570:
14564:
14562:
14559:
14557:
14554:
14552:
14549:
14546:
14542:
14538:
14534:
14530:
14526:
14522:
14519:
14518:
14516:
14512:
14509:
14507:
14503:
14493:
14490:
14488:
14485:
14483:
14480:
14478:
14475:
14473:
14472:Valproic acid
14470:
14468:
14465:
14463:
14460:
14458:
14455:
14453:
14450:
14448:
14445:
14443:
14440:
14438:
14435:
14433:
14430:
14428:
14425:
14423:
14420:
14418:
14417:Rezvilutamide
14415:
14413:
14410:
14408:
14405:
14403:
14400:
14398:
14395:
14393:
14392:Proxalutamide
14390:
14388:
14385:
14383:
14380:
14378:
14375:
14373:
14370:
14368:
14365:
14363:
14360:
14358:
14355:
14353:
14351:
14347:
14345:
14343:
14339:
14337:
14335:
14331:
14329:
14326:
14324:
14321:
14319:
14316:
14314:
14311:
14309:
14306:
14304:
14301:
14299:
14296:
14294:
14291:
14289:
14286:
14284:
14281:
14279:
14276:
14274:
14271:
14269:
14266:
14264:
14261:
14259:
14256:
14254:
14251:
14249:
14246:
14244:
14241:
14239:
14236:
14233:
14229:
14226:
14224:
14221:
14219:
14216:
14214:
14211:
14209:
14206:
14204:
14201:
14199:
14196:
14194:
14191:
14189:
14186:
14183:
14179:
14175:
14171:
14167:
14163:
14160:
14158:
14155:
14153:
14150:
14148:
14145:
14143:
14140:
14138:
14135:
14133:
14130:
14128:
14125:
14123:
14120:
14118:
14115:
14113:
14110:
14108:
14107:-Bicalutamide
14106:
14101:
14100:Nonsteroidal:
14098:
14097:
14094:
14091:
14089:
14086:
14084:
14081:
14079:
14076:
14074:
14071:
14069:
14066:
14064:
14061:
14059:
14056:
14054:
14051:
14049:
14046:
14044:
14041:
14039:
14036:
14034:
14031:
14029:
14026:
14024:
14021:
14019:
14016:
14014:
14011:
14009:
14006:
14004:
14001:
13999:
13996:
13994:
13991:
13989:
13986:
13984:
13981:
13979:
13976:
13974:
13971:
13969:
13968:Guggulsterone
13966:
13964:
13961:
13959:
13956:
13954:
13951:
13949:
13946:
13944:
13941:
13939:
13936:
13934:
13931:
13929:
13926:
13924:
13921:
13919:
13916:
13914:
13911:
13909:
13906:
13904:
13901:
13899:
13896:
13894:
13891:
13889:
13886:
13884:
13881:
13879:
13876:
13874:
13871:
13869:
13866:
13864:
13861:
13859:
13856:
13854:
13851:
13849:
13846:
13844:
13841:
13839:
13836:
13834:
13831:
13829:
13826:
13824:
13821:
13819:
13816:
13814:
13811:
13808:
13807:
13805:
13801:
13795:
13792:
13790:
13787:
13785:
13782:
13780:
13777:
13774:
13773:
13770:
13767:
13765:
13762:
13760:
13757:
13755:
13752:
13750:
13747:
13745:
13742:
13740:
13737:
13735:
13732:
13730:
13727:
13725:
13722:
13720:
13717:
13715:
13712:
13710:
13707:
13705:
13702:
13700:
13697:
13695:
13692:
13690:
13687:
13685:
13682:
13680:
13677:
13675:
13672:
13670:
13667:
13665:
13662:
13660:
13657:
13655:
13652:
13650:
13647:
13645:
13642:
13640:
13637:
13635:
13632:
13630:
13627:
13625:
13622:
13620:
13617:
13615:
13612:
13610:
13607:
13606:Nonsteroidal:
13604:
13603:
13601:
13596:
13590:
13584:
13581:
13579:
13576:
13574:
13571:
13569:
13566:
13564:
13561:
13559:
13558:5α-Androstane
13556:
13554:
13551:
13548:
13547:
13544:
13541:
13539:
13536:
13534:
13531:
13528:
13527:
13524:
13521:
13519:
13516:
13513:
13512:
13509:
13506:
13502:
13499:
13498:
13497:
13494:
13492:
13489:
13487:
13484:
13481:
13477:
13473:
13470:
13468:
13465:
13461:
13458:
13457:
13456:
13453:
13450:
13446:
13443:
13441:
13438:
13436:
13433:
13431:
13428:
13424:
13421:
13420:
13419:
13416:
13414:
13411:
13409:
13406:
13404:
13401:
13398:
13397:
13394:
13391:
13389:
13386:
13384:
13381:
13378:
13377:
13374:
13371:
13367:
13366:Ethandrostate
13364:
13363:
13362:
13359:
13357:
13354:
13351:
13350:
13347:
13344:
13341:
13340:
13337:
13334:
13331:
13330:
13327:
13324:
13322:
13319:
13316:
13315:
13312:
13309:
13307:
13304:
13302:
13299:
13297:
13294:
13292:
13289:
13287:
13284:
13282:
13279:
13277:
13274:
13272:
13269:
13267:
13266:Ethylestrenol
13264:
13262:
13259:
13257:
13254:
13252:
13249:
13247:
13244:
13241:
13240:
13237:
13234:
13232:
13229:
13227:
13224:
13222:
13219:
13217:
13214:
13212:
13209:
13207:
13204:
13200:
13197:
13195:
13192:
13191:
13190:
13187:
13185:
13182:
13180:
13177:
13175:
13172:
13170:
13167:
13165:
13162:
13159:
13158:
13155:
13152:
13150:
13147:
13145:
13142:
13138:
13135:
13134:
13132:
13128:
13125:
13123:
13120:
13116:
13113:
13111:
13108:
13106:
13103:
13101:
13098:
13097:
13096:
13093:
13091:
13088:
13086:
13083:
13081:
13078:
13076:
13073:
13071:
13068:
13066:
13063:
13061:
13058:
13056:
13053:
13051:
13048:
13046:
13043:
13041:
13038:
13035:
13034:
13031:
13028:
13026:
13023:
13021:
13018:
13015:
13014:
13009:
13006:
13004:
13001:
13000:
12999:
12996:
12994:
12991:
12987:
12984:
12982:
12979:
12977:
12974:
12972:
12969:
12968:
12967:
12964:
12960:
12957:
12956:
12955:
12952:
12950:
12947:
12943:
12940:
12939:
12938:
12935:
12931:
12928:
12927:
12926:
12923:
12921:
12918:
12916:
12914:
12910:
12905:
12901:
12898:
12896:
12893:
12891:
12888:
12887:
12886:
12883:
12881:
12878:
12876:
12873:
12871:
12868:
12866:
12863:
12859:
12856:
12855:
12854:
12851:
12849:
12846:
12844:
12841:
12839:
12836:
12832:
12829:
12828:
12827:
12824:
12822:
12819:
12816:
12815:
12812:
12809:
12805:
12802:
12801:
12800:
12797:
12795:
12792:
12788:
12785:
12784:
12783:
12780:
12778:
12775:
12771:
12768:
12767:
12766:
12763:
12761:
12758:
12756:
12753:
12751:
12748:
12746:
12743:
12739:
12736:
12735:
12734:
12731:
12727:
12724:
12723:
12721:
12717:
12714:
12712:
12709:
12707:
12704:
12702:
12699:
12695:
12692:
12691:
12690:
12687:
12685:
12682:
12680:
12677:
12675:
12672:
12670:
12667:
12665:
12662:
12660:
12657:
12655:
12652:
12650:
12647:
12645:
12642:
12639:
12638:
12633:
12630:
12628:
12625:
12624:
12622:
12618:
12615:
12613:
12610:
12608:
12605:
12603:
12600:
12598:
12595:
12593:
12590:
12586:
12583:
12581:
12578:
12577:
12576:
12573:
12571:
12568:
12564:
12561:
12560:
12559:
12556:
12552:
12549:
12547:
12544:
12542:
12539:
12538:
12537:
12534:
12532:
12529:
12525:
12522:
12521:
12520:
12517:
12515:
12512:
12510:
12507:
12503:
12500:
12498:
12495:
12493:
12490:
12488:
12485:
12484:
12483:
12480:
12478:
12475:
12473:
12470:
12468:
12465:
12463:
12460:
12458:
12455:
12453:
12450:
12448:
12445:
12443:
12440:
12437:
12436:
12434:
12430:
12427:
12422:
12416:
12412:
12409:
12402:
12397:
12395:
12390:
12388:
12383:
12382:
12379:
12373:
12366:
12353:
12350:Green nodes:
12341:
12337:
12334:Brown nodes:
12325:
12321:
12309:
12297:
12285:
12273:
12261:
12248:
12244:
12220:
12213:
12204:
12197:
12192:
12185:
12176:
12169:
12168:Sphingolipids
12162:
12161:sphingolipids
12153:
12144:
12137:
12136:Glycerolipids
12130:
12129:phospholipids
12121:
12114:
12106:
12102:
12097:
12090:
12081:
12074:
12065:
12058:
12051:
12044:
12043:proteoglycans
12039:
12038:Glycoproteins
12032:
12025:
12016:
12009:
12002:
11995:
11990:
11983:
11975:
11971:
11965:
11961:
11953:
11948:
11940:
11935:
11928:
11918:
11911:
11904:
11897:
11888:
11880:
11875:
11868:
11864:
11855:
11848:
11841:
11834:
11827:
11822:
11815:
11808:
11803:
11794:
11789:
11780:
11771:
11762:
11755:
11748:
11739:
11730:
11721:
11712:
11705:
11696:
11689:
11680:
11673:
11666:
11659:
11652:
11645:
11638:
11629:
11622:
11613:
11606:
11599:
11592:
11585:
11578:
11571:
11564:
11559:
11552:
11545:
11536:
11532:
11526:
11519:
11512:
11507:
11506:
11505:
11492:
11491:
11490:
11479:
11478:
11477:
11466:
11465:
11464:
11458:
11447:
11446:
11445:
11432:
11431:
11430:
11419:
11418:
11417:
11406:
11405:
11404:
11393:
11392:
11391:
11380:
11379:
11378:
11367:
11366:
11365:
11352:
11351:
11350:
11337:
11336:
11335:
11322:
11321:
11320:
11309:
11308:
11307:
11305:carbon intake
11294:
11293:
11292:
11277:
11276:
11275:
11262:
11261:
11260:
11247:
11246:
11245:
11234:
11233:
11232:
11217:
11216:
11215:
11202:
11201:
11200:
11187:
11186:
11185:
11172:
11171:
11170:
11159:
11154:
11153:
11141:
11140:
11130:
11129:
11117:
11116:
11102:
11101:
11087:
11086:
11074:
11073:
11061:
11060:
11048:
11047:
11033:
11032:
11020:
11019:
11005:
10997:
10996:
10990:
10985:
10978:
10973:
10971:
10966:
10964:
10959:
10958:
10955:
10939:
10936:
10934:
10931:
10927:
10924:
10923:
10922:
10919:
10918:
10916:
10912:
10902:
10899:
10897:
10894:
10892:
10889:
10887:
10884:
10882:
10879:
10878:
10876:
10872:
10866:
10863:
10860:
10856:
10853:
10852:
10850:
10848:
10844:
10841:
10838:
10834:
10829:
10825:
10811:
10810:Radiotrophism
10808:
10806:
10803:
10802:
10799:
10793:
10790:
10788:
10785:
10783:
10780:
10778:
10775:
10773:
10770:
10768:
10765:
10764:
10761:
10758:
10754:
10742:
10739:
10737:
10734:
10733:
10732:
10731:Glycosylation
10729:
10728:
10725:
10717:
10714:
10713:
10712:
10709:
10705:
10702:
10701:
10700:
10697:
10695:
10692:
10691:
10688:
10682:
10678:
10675:
10674:
10671:
10665:
10661:
10658:
10657:
10654:
10651:
10647:
10644:
10641:
10636:
10631:
10627:
10617:
10614:
10612:
10609:
10607:
10604:
10602:
10599:
10598:
10596:
10594:
10588:
10582:
10579:
10576:
10573:
10571:
10568:
10567:
10565:
10563:
10559:
10552:
10549:
10547:
10544:
10543:
10541:
10539:
10535:
10532:
10526:
10514:
10511:
10509:
10506:
10504:
10501:
10500:
10499:
10495:
10492:
10491:
10489:
10487:
10483:
10476:
10475:
10473:
10471:
10467:
10459:
10455:
10450:
10446:
10442:
10438:
10435:
10434:
10432:
10430:
10426:
10423:
10421:
10415:
10409:
10406:
10404:
10401:
10399:
10396:
10395:
10393:
10389:
10385:
10381:
10377:
10370:
10365:
10363:
10358:
10356:
10351:
10350:
10347:
10335:
10332:
10330:
10327:
10325:
10322:
10320:
10317:
10314:
10313:
10310:
10307:
10305:
10302:
10300:
10297:
10295:
10292:
10290:
10286:
10285:
10283:
10279:
10273:
10270:
10268:
10265:
10263:
10260:
10258:
10255:
10253:
10250:
10248:
10245:
10243:
10240:
10238:
10234:
10233:
10230:
10227:
10225:
10222:
10220:
10217:
10215:
10212:
10210:
10207:
10205:
10202:
10200:
10197:
10195:
10192:
10190:
10187:
10185:
10182:
10180:
10177:
10174:
10173:
10170:
10167:
10165:
10162:
10160:
10157:
10155:
10152:
10150:
10147:
10145:
10142:
10140:
10137:
10135:
10132:
10130:
10127:
10125:
10122:
10120:
10117:
10115:
10112:
10110:
10107:
10105:
10102:
10100:
10097:
10095:
10092:
10090:
10087:
10085:
10082:
10079:
10078:
10075:
10072:
10070:
10068:
10063:
10060:
10059:
10057:
10055:
10054:Neurosteroids
10051:
10041:
10040:Pregnanetriol
10038:
10036:
10033:
10031:
10028:
10026:
10023:
10020:
10019:
10016:
10013:
10011:
10008:
10006:
10003:
10001:
9998:
9996:
9993:
9991:
9988:
9986:
9983:
9981:
9978:
9977:
9975:
9973:
9969:
9962:
9958:
9954:
9951:
9949:
9946:
9944:
9941:
9939:
9936:
9934:
9931:
9929:
9926:
9924:
9921:
9919:
9916:
9914:
9911:
9909:
9906:
9904:
9901:
9899:
9896:
9894:
9891:
9889:
9886:
9884:
9881:
9878:
9877:
9874:
9871:
9869:
9866:
9864:
9861:
9859:
9856:
9854:
9851:
9849:
9846:
9844:
9841:
9839:
9836:
9834:
9831:
9829:
9826:
9823:
9822:
9819:
9816:
9814:
9811:
9809:
9806:
9804:
9801:
9799:
9796:
9794:
9791:
9789:
9786:
9784:
9781:
9779:
9776:
9774:
9771:
9769:
9766:
9764:
9761:
9759:
9756:
9754:
9751:
9749:
9746:
9744:
9743:17α-Estradiol
9741:
9739:
9736:
9734:
9731:
9729:
9726:
9724:
9721:
9718:
9717:
9715:
9713:
9709:
9703:
9700:
9698:
9695:
9693:
9690:
9688:
9685:
9683:
9680:
9678:
9675:
9673:
9670:
9668:
9665:
9663:
9660:
9658:
9655:
9653:
9650:
9648:
9645:
9643:
9640:
9638:
9635:
9633:
9630:
9628:
9625:
9623:
9620:
9618:
9615:
9612:
9611:
9608:
9605:
9603:
9600:
9598:
9595:
9593:
9590:
9588:
9585:
9583:
9580:
9578:
9575:
9573:
9570:
9568:
9565:
9563:
9560:
9558:
9555:
9553:
9550:
9548:
9545:
9543:
9540:
9538:
9535:
9533:
9530:
9528:
9525:
9523:
9520:
9519:
9517:
9515:
9511:
9508:
9506:
9502:
9492:
9489:
9487:
9484:
9482:
9479:
9477:
9474:
9472:
9469:
9467:
9464:
9462:
9459:
9457:
9454:
9452:
9449:
9447:
9444:
9442:
9439:
9438:
9436:
9434:
9430:
9424:
9421:
9419:
9416:
9413:
9412:
9409:
9406:
9404:
9401:
9399:
9396:
9394:
9391:
9389:
9386:
9384:
9381:
9379:
9376:
9374:
9371:
9369:
9366:
9364:
9361:
9359:
9356:
9354:
9351:
9349:
9346:
9344:
9341:
9340:
9338:
9336:
9332:
9329:
9327:
9323:
9317:
9314:
9312:
9309:
9307:
9304:
9302:
9299:
9297:
9294:
9292:
9289:
9287:
9285:
9280:
9278:
9276:
9271:
9269:
9266:
9265:
9263:
9261:
9257:
9253:
9250:
9243:
9238:
9236:
9231:
9229:
9224:
9223:
9220:
9204:
9201:
9199:
9196:
9194:
9191:
9189:
9186:
9184:
9181:
9179:
9176:
9175:
9173:
9171:
9166:
9159:
9155:
9151:
9149:
9146:
9144:
9141:
9139:
9138:Isofucosterol
9136:
9134:
9131:
9129:
9126:
9124:
9121:
9119:
9116:
9115:
9113:
9111:
9106:
9103:
9099:
9092:
9088:
9086:
9084:
9079:
9077:
9075:
9070:
9069:
9067:
9065:
9060:
9055:
9049:
9046:
9044:
9041:
9039:
9036:
9034:
9031:
9029:
9026:
9025:
9022:
9019:
9017:
9014:
9012:
9009:
9007:
9004:
9002:
8999:
8998:
8995:
8992:
8990:
8987:
8985:
8982:
8980:
8977:
8975:
8972:
8971:
8968:
8965:
8963:
8960:
8958:
8955:
8953:
8950:
8949:
8947:
8945:
8940:
8930:
8927:
8925:
8922:
8920:
8917:
8915:
8912:
8910:
8907:
8905:
8902:
8900:
8897:
8895:
8892:
8891:
8888:
8885:
8883:
8879:
8869:
8866:
8864:
8861:
8860:
8858:
8856:
8852:
8846:
8843:
8841:
8838:
8837:
8835:
8831:
8825:
8822:
8820:
8817:
8815:
8812:
8810:
8807:
8805:
8802:
8801:
8799:
8797:
8792:
8786:
8783:
8781:
8778:
8776:
8773:
8772:
8770:
8768:
8767:Ketone bodies
8764:
8758:
8755:
8753:
8750:
8748:
8745:
8743:
8740:
8738:
8735:
8734:
8732:
8730:
8725:
8722:
8720:
8716:
8712:
8709:
8705:
8698:
8693:
8691:
8686:
8684:
8679:
8678:
8675:
8662:
8659:
8656:
8653:
8652:
8650:
8646:
8639:
8635:
8631:
8630:
8628:
8624:
8617:
8615:3-oxo-α-ionol
8614:
8613:
8611:
8607:
8600:
8598:
8595:
8593:
8590:
8589:
8587:
8584:
8580:
8570:
8567:
8565:
8562:
8560:
8557:
8555:
8552:
8550:
8549:Cryptoxanthin
8547:
8545:
8544:Canthaxanthin
8542:
8541:
8539:
8536:
8532:
8526:
8523:
8521:
8518:
8516:
8513:
8511:
8508:
8506:
8503:
8501:
8498:
8496:
8495:Beta-Carotene
8493:
8491:
8488:
8487:
8485:
8483:
8479:
8476:
8473:
8468:
8464:
8457:
8455:Ferrugicadiol
8454:
8453:
8451:
8447:
8435:
8432:
8430:
8427:
8425:
8422:
8420:
8417:
8416:
8414:
8412:
8409:
8407:Serratenediol
8406:
8404:
8401:
8399:
8396:
8394:
8391:
8390:
8388:
8384:
8378:
8375:
8373:
8370:
8368:
8365:
8363:
8360:
8358:
8355:
8351:
8348:
8346:
8343:
8341:
8338:
8336:
8333:
8330:
8328:
8325:
8324:
8323:
8320:
8319:
8317:
8315:
8311:
8308:
8305:
8304:Triterpenoids
8301:
8294:
8293:
8291:
8288:
8284:
8273:
8270:
8267:
8265:
8262:
8259:
8257:Mercusic acid
8256:
8254:
8251:
8248:
8246:
8243:
8240:
8238:Communic acid
8237:
8235:
8232:
8231:
8229:
8227:
8223:
8217:
8214:
8212:
8209:
8207:
8204:
8203:
8201:
8197:
8190:
8187:
8184:
8182:
8179:
8177:
8174:
8173:
8171:
8167:
8161:
8158:
8155:
8152:
8149:
8148:
8146:
8142:
8136:
8133:
8131:
8128:
8127:
8125:
8121:
8114:
8112:
8109:
8107:
8104:
8103:
8101:
8097:
8094:
8091:
8087:
8080:
8077:
8075:
8072:
8069:
8067:
8064:
8061:
8059:
8056:
8054:
8051:
8049:
8046:
8044:
8041:
8039:
8036:
8035:
8033:
8030:
8026:
8016:
8013:
8011:
8008:
8006:
8003:
8001:
7998:
7996:
7993:
7991:
7988:
7987:
7985:
7981:
7975:
7972:
7970:
7967:
7965:
7962:
7959:
7955:
7952:
7950:
7947:
7945:
7942:
7940:
7937:
7936:
7934:
7930:
7924:
7921:
7919:
7916:
7914:
7911:
7909:
7906:
7904:
7901:
7899:
7896:
7894:
7891:
7890:
7888:
7884:
7881:
7875:
7865:
7862:
7860:
7857:
7855:
7852:
7850:
7847:
7844:
7840:
7836:
7833:
7832:
7830:
7826:
7820:
7817:
7815:
7812:
7810:
7807:
7806:
7804:
7800:
7794:
7791:
7789:
7786:
7785:
7783:
7779:
7776:
7764:
7760:
7754:
7751:
7749:
7746:
7735:
7732:
7731:
7729:
7726:
7722:
7715:
7712:
7709:
7706:
7703:
7700:
7697:
7694:
7690:
7686:
7685:
7683:
7679:
7674:
7670:
7666:
7658:
7653:
7651:
7646:
7644:
7639:
7638:
7635:
7623:
7620:
7619:
7617:
7613:
7607:
7604:
7602:
7599:
7598:
7596:
7592:
7586:
7583:
7581:
7578:
7576:
7573:
7572:
7570:
7568:
7564:
7558:
7555:
7554:
7552:
7545:
7539:
7536:
7534:
7531:
7530:
7528:
7521:
7515:
7512:
7511:
7509:
7502:
7496:
7493:
7491:
7488:
7486:
7485:Pregnenedione
7483:
7481:
7480:Pregnanedione
7478:
7476:
7473:
7471:
7470:Pregnanetriol
7468:
7466:
7463:
7459:
7456:
7454:
7451:
7449:
7446:
7442:
7439:
7438:
7436:
7429:
7423:
7420:
7419:
7417:
7410:
7404:
7400:
7397:
7395:
7392:
7390:
7387:
7385:
7382:
7380:
7377:
7375:
7372:
7370:
7367:
7365:
7362:
7360:
7357:
7355:
7352:
7350:
7347:
7345:
7342:
7340:
7337:
7333:
7330:
7328:
7327:Androstadiene
7325:
7323:
7320:
7316:
7313:
7312:
7310:
7303:
7297:
7294:
7292:
7289:
7287:
7284:
7280:
7277:
7275:
7272:
7270:
7267:
7263:
7260:
7259:
7257:
7250:
7244:
7241:
7240:
7238:
7231:
7226:
7219:
7214:
7212:
7207:
7205:
7200:
7199:
7196:
7187:
7183:
7179:
7174:
7170:
7164:
7160:
7156:
7152:
7147:
7142:
7138:
7134:
7130:
7126:
7122:
7119:(2): 115–24.
7118:
7114:
7109:
7106:
7100:
7096:
7091:
7086:
7082:
7078:
7074:
7070:
7066:
7061:
7056:
7050:
7046:
7042:
7038:
7033:
7021:
7017:
7013:
7009:
7003:
6999:
6994:
6993:
6971:
6967:
6961:
6945:
6941:
6935:
6919:
6915:
6909:
6893:
6889:
6883:
6867:
6863:
6857:
6841:
6837:
6831:
6815:
6811:
6805:
6797:
6793:
6789:
6785:
6778:
6770:
6766:
6762:
6756:
6752:
6748:
6744:
6737:
6729:
6725:
6721:
6717:
6710:
6702:
6696:
6692:
6688:
6684:
6677:
6675:
6673:
6664:
6660:
6656:
6652:
6648:
6641:
6639:
6630:
6626:
6621:
6616:
6612:
6608:
6604:
6600:
6596:
6592:
6588:
6581:
6573:
6567:
6563:
6555:
6553:
6536:
6532:
6528:
6522:
6520:
6503:
6499:
6495:
6488:
6480:
6476:
6471:
6466:
6462:
6458:
6454:
6447:
6439:
6435:
6431:
6427:
6424:(3): 231–51.
6423:
6419:
6412:
6404:
6400:
6396:
6392:
6389:(3): 761–73.
6388:
6384:
6377:
6369:
6365:
6360:
6355:
6350:
6345:
6341:
6337:
6333:
6326:
6318:
6314:
6310:
6306:
6302:
6298:
6291:
6275:
6271:
6270:
6263:
6255:
6249:
6245:
6241:
6237:
6233:
6226:
6210:
6206:
6200:
6192:
6188:
6184:
6180:
6177:(2): 155–64.
6176:
6172:
6165:
6157:
6153:
6148:
6143:
6139:
6135:
6131:
6124:
6122:
6120:
6103:
6099:
6095:
6091:
6087:
6083:
6079:
6075:
6071:
6067:
6060:
6052:
6048:
6043:
6038:
6034:
6030:
6026:
6019:
6011:
6007:
6003:
5999:
5995:
5991:
5987:
5983:
5976:
5968:
5964:
5959:
5954:
5949:
5944:
5940:
5936:
5932:
5925:
5917:
5913:
5909:
5905:
5901:
5897:
5893:
5889:
5882:
5874:
5870:
5866:
5862:
5858:
5854:
5847:
5845:
5833:
5829:
5825:
5821:
5817:
5813:
5809:
5806:(5): 637–46.
5805:
5801:
5794:
5787:
5779:
5775:
5771:
5767:
5764:(2): 171–83.
5763:
5759:
5752:
5750:
5741:
5737:
5732:
5727:
5723:
5719:
5714:
5709:
5705:
5701:
5697:
5690:
5682:
5678:
5673:
5668:
5664:
5660:
5657:(9): 3192–8.
5656:
5652:
5648:
5641:
5633:
5629:
5625:
5621:
5616:
5611:
5607:
5603:
5599:
5592:
5590:
5581:
5575:
5571:
5564:
5556:
5552:
5548:
5542:
5538:
5531:
5522:
5517:
5513:
5509:
5505:
5498:
5490:
5486:
5482:
5476:
5472:
5468:
5464:
5460:
5453:
5437:
5432:
5427:
5422:
5417:
5413:
5409:
5405:
5398:
5382:
5378:
5372:
5364:
5360:
5356:
5352:
5349:(6): 887–99.
5348:
5344:
5337:
5329:
5325:
5321:
5317:
5313:
5309:
5308:Contraception
5302:
5286:
5282:
5278:
5272:
5264:
5258:
5254:
5247:
5231:
5227:
5221:
5213:
5209:
5204:
5199:
5195:
5191:
5187:
5180:
5172:
5166:
5162:
5155:
5147:
5141:
5137:
5130:
5122:
5118:
5114:
5110:
5106:
5102:
5098:
5094:
5087:
5079:
5073:
5069:
5062:
5060:
5058:
5056:
5054:
5052:
5050:
5041:
5035:
5031:
5024:
5016:
5012:
5007:
5002:
4998:
4994:
4990:
4986:
4982:
4978:
4974:
4967:
4959:
4955:
4950:
4945:
4941:
4937:
4933:
4929:
4925:
4918:
4910:
4906:
4902:
4898:
4894:
4890:
4887:(2): 471–81.
4886:
4882:
4874:
4866:
4862:
4857:
4852:
4847:
4842:
4838:
4834:
4830:
4823:
4815:
4809:
4793:
4787:
4779:
4775:
4770:
4765:
4760:
4755:
4751:
4747:
4743:
4736:
4720:
4716:
4712:
4706:
4690:
4686:
4685:
4678:
4671:
4666:
4662:
4658:
4654:
4650:
4646:
4645:Eur J Biochem
4639:
4631:
4627:
4623:
4619:
4615:
4611:
4604:
4597:
4593:
4587:
4583:
4579:
4575:
4568:
4560:
4556:
4552:
4548:
4544:
4540:
4536:
4532:
4525:
4517:
4513:
4508:
4503:
4499:
4495:
4491:
4487:
4483:
4476:
4468:
4464:
4459:
4454:
4449:
4444:
4440:
4436:
4432:
4425:
4417:
4413:
4409:
4405:
4398:
4390:
4386:
4382:
4378:
4374:
4370:
4366:
4362:
4355:
4347:
4343:
4339:
4335:
4328:
4312:
4308:
4302:
4286:
4282:
4276:
4268:
4264:
4259:
4254:
4250:
4246:
4243:(1): 81–151.
4242:
4238:
4234:
4227:
4225:
4223:
4221:
4219:
4217:
4215:
4213:
4205:
4200:
4194:
4190:
4186:
4182:
4175:
4168:
4163:
4159:
4155:
4151:
4147:
4143:
4142:Eur J Biochem
4136:
4134:
4126:
4122:
4118:
4114:
4110:
4106:
4102:
4101:Eur J Biochem
4095:
4088:
4083:
4077:
4073:
4069:
4065:
4058:
4042:
4038:
4032:
4025:
4020:
4014:
4010:
4006:
4002:
3995:
3988:
3983:
3979:
3975:
3971:
3967:
3963:
3956:
3949:
3936:
3932:
3928:
3924:
3920:
3916:
3912:
3908:
3902:
3895:
3890:
3886:
3882:
3878:
3874:
3870:
3869:Eur J Biochem
3863:
3861:
3853:
3848:
3844:
3840:
3836:
3832:
3828:
3827:Eur J Biochem
3821:
3815:
3813:
3808:
3801:
3797:
3792:
3787:
3783:
3779:
3772:
3765:
3763:
3761:
3759:
3757:
3755:
3753:
3751:
3743:
3738:
3730:
3724:
3720:
3716:
3709:
3702:
3697:
3691:
3687:
3683:
3676:
3661:
3655:
3651:
3650:
3641:
3633:
3629:
3624:
3619:
3614:
3609:
3605:
3601:
3597:
3590:
3574:
3570:
3564:
3557:
3555:
3551:
3548:"Je nommerai
3545:
3544:
3536:
3520:
3516:
3513:(in French).
3512:
3508:
3504:
3498:
3482:
3478:
3474:
3467:
3451:
3447:
3443:
3437:
3435:
3426:
3422:
3418:
3414:
3410:
3406:
3402:
3398:
3391:
3383:
3377:
3373:
3366:
3364:
3362:
3345:
3341:
3337:
3331:
3327:
3323:
3319:
3315:
3311:
3306:
3290:
3286:
3282:
3278:
3274:
3270:
3267:
3266:
3258:
3251:
3249:
3247:
3245:
3240:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3188:Batrachotoxin
3186:
3184:
3183:Adrenal gland
3181:
3180:
3171:
3167:
3163:
3159:
3156:
3152:
3148:
3146:
3142:
3138:
3134:
3132:
3128:
3124:
3120:
3116:
3112:
3110:
3106:
3102:
3098:
3095:
3091:
3088:
3084:
3080:
3079:
3078:
3076:
3066:
3064:
3060:
3056:
3052:
3048:
3044:
3040:
3030:
3028:
3024:
3020:
3019:
3014:
3010:
3006:
3002:
2998:
2994:
2993:semisynthesis
2987:Semisynthesis
2979:
2977:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2946:
2942:
2932:
2930:
2926:
2922:
2918:
2914:
2912:
2908:
2904:
2900:
2896:
2891:
2888:
2884:
2874:
2872:
2868:
2864:
2860:
2856:
2852:
2848:
2844:
2840:
2836:
2832:
2822:
2820:
2816:
2812:
2808:
2804:
2800:
2796:
2792:
2787:
2785:
2781:
2777:
2760:See template.
2759:
2754:
2750:
2745:
2740:
2739:concentration
2736:
2726:
2722:
2720:19–45 nmol/L
2719:
2716:
2713:
2710:
2708:Luteal phase
2707:
2706:
2702:
2700:0.3–3 nmol/L
2699:
2696:
2693:
2690:
2687:
2685:
2681:
2677:
2674:
2671:
2668:
2665:
2663:Luteal phase
2662:
2661:
2657:
2654:
2651:
2648:
2645:
2642:
2640:
2636:
2632:
2629:
2626:
2623:
2620:
2617:
2616:
2612:
2609:
2606:
2603:
2600:
2598:Luteal phase
2597:
2596:
2592:
2589:
2586:
2583:
2580:
2577:
2575:
2571:
2567:
2564:
2561:
2558:
2555:
2552:
2551:
2548:80–180 pg/mL
2547:
2544:
2541:
2538:
2535:
2533:Luteal phase
2532:
2531:
2528:30–110 pg/mL
2527:
2524:
2521:
2518:
2515:
2512:
2510:
2506:
2502:
2499:
2496:
2493:
2490:
2485:
2483:
2480:
2479:
2476:89–350 ng/dL
2475:
2472:
2469:
2466:
2463:
2458:
2456:
2453:
2449:
2445:
2442:
2439:
2436:
2433:
2428:
2426:
2423:
2422:
2418:
2415:
2412:
2409:
2406:
2401:
2399:
2396:
2395:
2391:
2388:
2385:
2382:
2379:
2374:
2372:
2369:
2368:
2364:
2361:
2358:
2355:
2352:
2347:
2345:
2342:
2341:
2338:80–210 ng/dL
2337:
2334:
2331:
2328:
2325:
2320:
2318:
2315:
2311:
2303:
2297:
2296:
2265:
2258:
2253:
2251:
2246:
2244:
2239:
2238:
2231:
2230:
2225:
2221:
2217:
2213:
2209:
2206:
2202:
2201:Stromal cells
2199:
2196:
2193:
2189:
2185:
2182:, estriol in
2181:
2177:
2173:
2170:
2166:
2162:
2159:
2158:mitochondrion
2155:
2151:
2150:
2149:
2147:
2143:
2139:
2135:
2131:
2125:
2117:
2112:
2101:
2099:
2095:
2091:
2087:
2083:
2079:
2075:
2070:
2068:
2064:
2060:
2056:
2052:
2048:
2044:
2040:
2035:
2033:
2029:
2025:
2019:
2010:
2001:
1998:
1995:. Subsequent
1994:
1990:
1986:
1981:
1979:
1975:
1971:
1967:
1963:
1959:
1955:
1950:
1948:
1945:
1941:
1937:
1933:
1929:
1921:
1917:
1913:
1910:(DMAPP) form
1909:
1905:
1900:
1891:
1889:
1884:
1882:
1879:. Similar to
1878:
1874:
1870:
1869:phospholipids
1866:
1856:
1854:
1850:
1846:
1844:
1839:
1836:
1832:
1828:
1824:
1820:
1816:
1812:
1809:who graze on
1808:
1803:
1801:
1797:
1796:ring closures
1793:
1789:
1785:
1781:
1777:
1773:
1769:
1767:
1760:
1755:
1751:
1741:
1739:
1734:
1732:
1705:
1701:
1695:Testosterone
1692:
1688:
1682:Progesterone
1679:
1675:
1666:
1662:
1653:
1649:
1638:
1632:
1628:
1622:
1612:
1608:
1604:
1602:
1591:
1582:
1578:
1575:This section
1573:
1569:
1564:
1563:
1548:
1544:
1540:
1536:
1533:
1532:
1531:
1529:
1522:
1518:
1514:
1510:
1508:
1504:
1500:
1496:
1494:
1490:
1487:
1485:
1481:
1478:
1476:
1472:
1469:
1466:
1464:
1460:
1457:
1455:
1448:
1442:
1441:Neurosteroids
1439:
1438:
1437:
1427:
1424:
1423:
1421:
1418:
1414:
1410:
1407:
1406:
1404:
1401:
1397:
1393:
1389:
1385:
1382:
1381:
1379:
1376:
1375:
1373:
1370:
1363:
1359:
1355:
1352:
1351:
1349:
1346:
1342:
1338:
1334:
1331:
1330:
1328:
1325:
1324:
1322:
1319:
1318:
1317:
1315:
1304:
1295:
1291:
1288:This section
1286:
1282:
1277:
1276:
1260:
1256:
1253:
1250:
1247:excretion of
1246:
1242:
1238:
1234:
1230:
1226:
1222:
1219:
1216:
1212:
1208:
1204:
1200:
1196:
1193:
1192:
1191:
1189:
1185:
1181:
1177:
1173:
1169:
1165:
1161:
1157:
1147:
1145:
1141:
1137:
1133:
1129:
1128:Melanthiaceae
1125:
1121:
1111:
1109:
1105:
1104:S. cerevisiae
1101:
1097:
1093:
1089:
1088:
1083:
1082:
1077:
1073:
1068:
1066:
1061:
1057:
1052:
1050:
1046:
1042:
1038:
1034:
1030:
1026:
1016:
1014:
1011:
1007:
1003:
999:
994:
992:
987:
984:
982:
972:
969:November 2021
962:
956:
952:
949:This section
947:
943:
938:
937:
929:
927:
923:
919:
908:
898:
894:
890:
887:This section
885:
876:
875:
867:
863:
860:
856:
852:
846:
844:
840:
836:
831:
828:
824:
823:hydroxy group
819:
817:
813:
809:
805:
801:
797:
793:
789:
784:
782:
778:
773:
769:
764:
760:
755:
751:
749:
745:
742:
738:
733:
731:
727:
723:
719:
714:
712:
711:hydroxy group
708:
704:
700:
696:
691:
687:
683:
679:
675:
671:
657:
652:
647:
643:
638:
634:
630:
626:
622:
618:
614:
612:
608:
604:
600:
596:
588:
587:configuration
584:
581:
578:
575:
571:
570:
569:
567:
563:
553:
550:, a plant or
549:
543:
538:
534:
528:
523:
519:
513:
508:
504:
500:
496:
490:
485:
481:
477:
476:Dexamethasone
471:
466:
463:often present
462:
458:
454:
450:
444:
439:
436:
432:
428:
422:
417:
416:
414:
411:
409:
405:
401:
397:
393:
389:
385:
381:
377:
371:
370:stereoisomers
366:
359:
355:
350:
346:
327:intermediate.
326:
322:
318:
314:
310:
306:
293:
281:
272:
270:
263:
259:
255:
251:
250:hydroxy group
247:
243:
239:
235:
231:
227:
223:
219:
214:
212:
208:
204:
201:
200:Ancient Greek
197:
192:
190:
187:
183:
179:
175:
171:
168:
164:
160:
156:
152:
151:dexamethasone
148:
144:
140:
136:
132:
129:
125:
121:
117:
112:
110:
106:
102:
98:
90:
86:
81:
77:
73:
69:
65:
48:
44:
40:
33:
28:
19:
20809:Mifepristone
20793:Progesterone
20788:Pregnenolone
20783:Mifepristone
20668:Darolutamide
20664:
20653:Toripristone
20648:RTI 3021–022
20618:Lilopristone
20613:Aglepristone
20609:
20565:
20544:Telapristone
20465:
20430:
20380:
20339:Drospirenone
20325:
20112:Quingestanol
20087:Norgestimate
20082:Norgesterone
20077:Noretynodrel
19993:Etonogestrel
19919:Progestins:
19916:
19910:Trimegestone
19895:Promegestone
19796:
19785:Proligestone
19725:Melengestrol
19690:Medrogestone
19625:Flumedroxone
19580:Cymegesolate
19570:Clomegestone
19446:
19401:
19395:Quingestrone
19385:Progesterone
19316:
19194:Nitrendipine
19140:
19119:Trimegestone
19044:Progesterone
19039:Pregnenolone
18999:Medrogestone
18969:Drospirenone
18895:
18846:Prednazoline
18836:Prednisolone
18569:
18554:Zavacorilant
18544:Toripristone
18534:Telapristone
18529:RTI 3021–022
18524:RTI 3021–012
18464:Lilopristone
18459:Ketoconazole
18444:Dazucorilant
18409:Aglepristone
18335:
18319:Quingestrone
18309:Promegestone
18304:Progesterone
18274:Medrogestone
18244:Etonogestrel
18190:
18147:Domoprednate
18133:
18083:Itrocinonide
17936:
17865:Prednylidene
17768:Halometasone
17747:Fluticasone
17707:Fluocinolone
17685:Fluclorolone
17581:Clocortolone
17497:
17445:Pregnenolone
17406:Prednazoline
17396:Prednisolone
17384:Prebediolone
17246:Dichlorisone
17072:
16699:
16689:
16613:Mepitiostane
16561:Epitiostanol
16430:Ormeloxifene
16355:Lasofoxifene
16265:Camizestrant
16260:Broparestrol
16250:Bazedoxifene
16172:rotundifuran
16121:alkylphenols
16088:
16071:β-zearalenol
16067:α-zearalenol
16053:stigmasterol
16045:β-sitosterol
16041:Phytosterols
16009:triclocarban
16005:methoxychlor
15958:
15940:Lavender oil
15934:tectorigenin
15866:formononetin
15740:
15715:
15586:
15578:
15378:
15362:Quinestradol
15352:Promestriene
15327:Noretynodrel
15191:Estromustine
15144:Estramustine
15079:
14986:testosterone
14723:
14611:Testosterone
14397:Pyrilutamide
14349:
14341:
14333:
14298:Lavender oil
14288:Ketoconazole
14253:Enzalutamide
14223:Darolutamide
14157:Bicalutamide
14132:Atraric acid
14104:
14099:
14083:Trimegestone
14038:Promegestone
14003:Mifepristone
13978:Medrogestone
13923:Drospirenone
13878:Clascoterone
13809:
13775:
13719:JNJ-37654032
13714:JNJ-28330835
13709:JNJ-26146900
13605:
13549:
13529:
13514:
13496:Quingestanol
13413:Etonogestrel
13399:
13379:
13352:
13342:
13332:
13317:
13301:Propetandrol
13242:
13231:Oxymetholone
13206:Methasterone
13160:
13154:Tiomesterone
13144:Oxymesterone
13036:
13016:
12937:Norclostebol
12912:
12908:
12817:
12755:Mepitiostane
12750:Epitiostanol
12733:Drostanolone
12684:Androsterone
12640:
12621:+dutasteride
12617:Testosterone
12585:DHEA sulfate
12438:
12318:Grey nodes:
12306:Blue nodes:
12294:Pink nodes:
12212:cannabinoids
12202:
12050:Chlorophylls
12001:Antioxidants
11754:Serine group
11665:Photosystems
11651:P-glycerates
11598:P-glycerates
11563:sialic acids
11558:Amino sugars
11510:
11498:
11497:
11485:
11484:
11472:
11471:
11453:
11452:
11438:
11437:
11425:
11424:
11412:
11411:
11399:
11398:
11386:
11385:
11373:
11372:
11358:
11357:
11343:
11342:
11328:
11327:
11315:
11314:
11300:
11299:
11283:
11282:
11268:
11267:
11253:
11252:
11243:Fermentation
11240:
11239:
11223:
11222:
11208:
11207:
11193:
11192:
11178:
11177:
11163:
11162:
11157:
11146:
11135:
11122:
11107:
11092:
11079:
11066:
11053:
11038:
11025:
11012:
10880:
10711:Galactolysis
10681:Glycogenesis
10486:Fermentation
10458:ATP synthase
10315:
10287:
10267:Androsterone
10262:Androstenone
10235:
10224:DHEA sulfate
10214:Androsterone
10176:Androstanes:
10175:
10159:Progesterone
10149:Pregnenolone
10144:Pregnanolone
10080:
10066:
10062:Cholestanes:
10061:
10030:Pregnanediol
10022:Metabolites:
10021:
9980:Progesterone
9972:Progestogens
9880:Metabolites:
9879:
9858:DHEA sulfate
9824:
9719:
9614:Metabolites:
9613:
9607:Testosterone
9572:DHEA sulfate
9557:Androsterone
9505:Sex steroids
9415:Metabolites:
9414:
9408:Progesterone
9403:Pregnenolone
9291:Pregnenolone
9283:
9274:
9251:
9154:Phytosterols
9128:Obtusifoliol
9118:Cycloartenol
9082:
9073:
9063:
8707:
8601:Gutta-balatá
8597:Gutta percha
8535:Xanthophylls
8515:Neurosporene
8434:Moronic acid
8424:Ursolic acid
8367:Testosterone
8350:Stigmasterol
8335:Cycloartenol
8322:Phytosterols
8313:
8264:Pimaric acid
8234:Abietic acid
8185:Manoyl oxide
8160:Salvinorin A
8150:
8090:Diterpenoids
7954:Thujaplicins
7879:(2,modified)
7819:Phellandrene
7763:Monoterpenes
7713:
7692:
7688:
7681:Basic forms:
7475:Pregnenediol
7465:Pregnanediol
7462:Substituted:
7461:
7458:Pregnatriene
7444:
7354:Androstenone
7349:Androstanone
7336:Substituted:
7335:
7318:
7283:Substituted:
7282:
7265:
7224:
7186:the original
7181:
7154:
7116:
7112:
7072:
7068:
7036:
7024:. Retrieved
6997:
6989:Bibliography
6974:. Retrieved
6960:
6948:. Retrieved
6934:
6922:. Retrieved
6908:
6896:. Retrieved
6882:
6870:. Retrieved
6856:
6844:. Retrieved
6830:
6818:. Retrieved
6804:
6787:
6783:
6777:
6742:
6736:
6719:
6715:
6709:
6682:
6654:
6650:
6646:
6597:(2): 310–1.
6594:
6590:
6580:
6561:
6539:. Retrieved
6530:
6506:. Retrieved
6497:
6487:
6460:
6456:
6446:
6421:
6417:
6411:
6386:
6382:
6376:
6339:
6335:
6325:
6300:
6296:
6290:
6278:. Retrieved
6268:
6262:
6235:
6225:
6213:. Retrieved
6199:
6174:
6171:Cell Calcium
6170:
6164:
6137:
6133:
6106:. Retrieved
6073:
6069:
6059:
6032:
6028:
6018:
5985:
5981:
5975:
5938:
5934:
5924:
5894:(3): 221–6.
5891:
5887:
5881:
5856:
5852:
5832:the original
5803:
5799:
5786:
5761:
5757:
5703:
5699:
5689:
5654:
5650:
5640:
5605:
5601:
5569:
5563:
5536:
5530:
5511:
5507:
5497:
5462:
5452:
5440:. Retrieved
5411:
5407:
5397:
5385:. Retrieved
5371:
5346:
5342:
5336:
5311:
5307:
5301:
5289:. Retrieved
5280:
5271:
5252:
5246:
5234:. Retrieved
5220:
5196:(2): 203–7.
5193:
5189:
5179:
5160:
5154:
5135:
5129:
5096:
5092:
5086:
5067:
5032:. Springer.
5029:
5023:
4980:
4976:
4966:
4931:
4927:
4917:
4884:
4880:
4873:
4836:
4832:
4822:
4796:. Retrieved
4786:
4749:
4745:
4735:
4723:. Retrieved
4714:
4705:
4693:. Retrieved
4683:
4677:
4668:
4648:
4644:
4638:
4613:
4609:
4603:
4595:
4573:
4567:
4534:
4530:
4524:
4489:
4485:
4475:
4438:
4434:
4424:
4407:
4403:
4397:
4364:
4360:
4354:
4337:
4333:
4327:
4315:. Retrieved
4301:
4289:. Retrieved
4275:
4240:
4236:
4202:
4180:
4174:
4165:
4145:
4141:
4124:
4104:
4100:
4094:
4085:
4063:
4057:
4045:. Retrieved
4031:
4022:
4000:
3994:
3985:
3965:
3961:
3955:
3946:
3939:. Retrieved
3914:
3910:
3901:
3892:
3872:
3868:
3850:
3830:
3826:
3820:
3804:
3781:
3777:
3737:
3718:
3708:
3699:
3685:
3675:
3663:. Retrieved
3648:
3640:
3603:
3599:
3589:
3577:. Retrieved
3563:
3554:cholesterine
3553:
3550:cholesterine
3549:
3547:
3542:
3535:
3525:11 September
3523:. Retrieved
3514:
3510:
3497:
3485:. Retrieved
3476:
3466:
3454:. Retrieved
3450:the original
3445:
3400:
3396:
3390:
3371:
3348:. Retrieved
3335:
3313:
3309:
3304:
3296:. Retrieved
3268:
3263:
3151:Derek Barton
3127:Philip Hench
3075:Nobel Prizes
3073:A number of
3072:
3053:begins from
3036:
3016:
3001:phytosterols
2990:
2978:techniques.
2938:
2928:
2916:
2915:
2892:
2882:
2880:
2859:hydroxylated
2849:gene can be
2828:
2815:5α-Reductase
2788:
2773:
2757:
2752:
2748:
2743:
2738:
2734:
2684:Progesterone
2633:10–38 pg/mL
2593:10–98 pg/mL
2503:20–81 ng/dL
2482:Testosterone
2419:10–57 pg/mL
2392:10–70 pg/mL
2344:Testosterone
2273:Reproductive
2270:Sex hormone
2228:
2188:testosterone
2154:pregnenolone
2134:progestogens
2127:
2086:rosuvastatin
2071:
2036:
2030:(DMAPP) and
2021:
1982:
1976:(DMAPP) and
1951:
1944:triterpenoid
1936:cycloartenol
1925:
1885:
1862:
1841:
1823:biosynthetic
1817:(shown) and
1804:
1783:
1779:
1770:
1749:
1747:
1740:sidechains.
1735:
1716:
1669:Cholic acid
1656:Cholesterol
1598:
1585:
1581:adding to it
1576:
1553:By structure
1528:secosteroids
1525:
1517:cardenolides
1507:phytosterols
1468:Aminosteroid
1435:
1409:Testosterone
1384:Progesterone
1378:Progestogens
1372:Sex steroids
1311:
1301:January 2019
1298:
1294:adding to it
1289:
1249:electrolytes
1227:classes the
1215:progestogens
1203:reproduction
1201:and support
1195:Sex hormones
1164:ecdysteroids
1153:
1140:phytosterols
1117:
1103:
1085:
1079:
1069:
1060:phytosterols
1053:
1022:
1010:triterpinoid
1002:myxobacteria
995:
988:
985:
979:
966:
950:
915:
902:
892:
888:
864:
847:
832:
820:
808:pregnenolone
792:progesterone
785:
752:
734:
715:
699:testosterone
695:progesterone
667:
637:biosynthetic
629:prototypical
607:progesterone
603:testosterone
592:
566:contractions
559:
548:β-Sitosterol
533:Medrogestone
518:Progesterone
503:triterpenoid
499:biosynthetic
427:Testosterone
412:
404:cyclopentane
400:phenanthrene
390:. The three
374:
334:Nomenclature
325:biosynthetic
262:secosteroids
234:cyclopentane
220:) is called
215:
210:
202:
193:
178:cycloartenol
174:opisthokonts
139:testosterone
113:
96:
94:
76:
46:
37:This is the
31:
20802:Antagonists
20628:Onapristone
20603:Antagonists
20374:Spirorenone
20344:Mespirenone
20033:Lynestrenol
19983:Ethisterone
19961:Desogestrel
19941:Altrenogest
19900:Segesterone
19875:Norgestomet
19865:Nomegestrol
19840:Gestadienol
19825:Demegestone
19780:Pentarane A
19600:Edogestrone
19590:Delmadinone
19550:Cismadinone
19440:Trengestone
19370:Dimepregnen
19204:PF-03882845
19199:Ocedurenone
19164:Esaxerenone
19149:Apararenone
19109:Spiroxasone
19099:Spirorenone
19009:Metribolone
19004:Mespirenone
18889:Antagonists
18751:Aldosterone
18494:Onapristone
18434:CORT-108297
18391:Antagonists
18294:Norgestomet
18289:Metribolone
18234:Desogestrel
18214:Cyproterone
18088:Rofleponide
18078:Halcinonide
18073:Formocortal
18039:Flunisolide
18034:Flumoxonide
18007:Drocinonide
17970:Cicortonide
17965:Ciclesonide
17802:Meclorisone
17773:Icometasone
17639:Diflorasone
17617:Descinolone
17593:Cloticasone
17569:Clobetasone
17357:Loteprednol
17333:Halopredone
17309:Fluperolone
16958:Zearalenone
16910:Antagonists
16886:Resveratrol
16851:Nonylphenol
16846:Niacinamide
16762:Bisphenol A
16752:Aldosterone
16581:Glyceollins
16529:Antagonists
16520:Zuclomifene
16515:Zindoxifene
16425:NNC 45-1506
16420:NNC 45-0781
16415:NNC 45-0320
16410:NNC 45-0095
16405:Nitromifene
16385:Miproxifene
16335:Fispemifene
16310:Enclomifene
16305:Droloxifene
16285:CN-55945-27
16230:Afimoxifene
16220:Acefluranol
16111:rhaponticin
16107:resveratrol
16103:Stilbenoids
16075:zearalenone
16063:zearalanone
16049:campesterol
15981:alternariol
15914:pinocembrin
15858:epicatechin
15830:biochanin A
15770:Chalconoids
15664:Terfluranol
15639:Quadrosilan
15511:Elacestrant
15412:Allenestrol
15287:Lynestrenol
15211:Estropipate
15181:Estrofurate
15032:Clomestrone
15012:Atrimustine
14962:Abiraterone
14916:alfatradiol
14596:Osteocalcin
14477:Vinclozolin
14462:Thalidomide
14457:Seviteronel
14387:Procymidone
14323:Masofaniten
14278:Inocoterone
14182:bisphenol S
14178:bisphenol F
14174:bisphenol A
14152:BAY-1024767
14127:Apalutamide
14073:Spiroxasone
14068:Spirorenone
14048:Rosterolone
13988:Mespirenone
13933:Edogestrone
13903:Delanterone
13893:Cyproterone
13883:Clometerone
13853:Benorterone
13838:Abiraterone
13803:Antagonists
13734:PF-06260414
13639:BMS-564,929
13563:Alternariol
13455:Lynestrenol
13408:Desogestrel
13291:Norboletone
13281:Metribolone
13226:Oxandrolone
13184:Mestanolone
13149:Penmesterol
13080:Formebolone
13045:Calusterone
13040:Bolasterone
12794:Prostanozol
12765:Mesterolone
12342:metabolism.
12326:metabolism.
12282:Red nodes:
12219:Eicosanoids
12184:fatty acids
12113:Cholesterol
12101:carotenoids
12080:Polyketides
12015:Nucleotides
11970:tocopherols
11934:Calciferols
11847:Amino acids
11840:amino acids
11770:amino acids
11745:Respiratory
11488:Proteolysis
11475:Translation
11462:replication
11428:MEP pathway
11415:MVA pathway
11376:Lipogenesis
11348:deamination
11138:Peroxisomal
11030:respiration
10837:lipogenesis
10699:Fructolysis
10513:Lactic acid
10189:7-Keto-DHEA
10074:Cholesterol
9863:7-Keto-DHEA
9481:Aldosterone
9268:Cholesterol
9059:Cholesterol
9048:Cholesterol
9043:Desmosterol
9021:Cholesterol
9011:Lathosterol
8989:Zymosterone
8944:Cholesterol
8704:Cholesterol
8569:Rubixanthin
8559:Astaxanthin
8520:Phytofluene
8472:Carotenoids
8362:Cholesterol
8357:Tocopherols
8327:Campesterol
8226:Resin acids
8211:Gibberellin
8206:Aphidicolin
8199:Tetracyclic
8074:Longifolene
8038:Artemisinin
8015:Umbellulone
7903:Citronellol
7893:Citronellal
7606:Secosteroid
7514:Cardanolide
7495:5β-Pregnane
7490:5α-Pregnane
7453:Pregnadiene
7403:Etiocholane
7344:Androstenol
7339:Androstanol
7279:Estratriene
6950:27 November
6898:27 November
6872:27 November
6846:27 November
6820:27 November
6492:Steimer T.
6280:12 February
6215:12 February
5941:: 383–413.
5859:: 585–621.
5281:rgd.mcw.edu
5236:12 February
5099:(1): 3–19.
4725:12 February
4695:12 February
3941:19 February
3579:22 November
3517:: 339–372.
3503:Chevreul ME
3456:28 November
3298:21 February
3059:1-tetralone
2997:cholesterol
2948:side chains
2945:phytosterol
2851:upregulated
2807:17,20 Lyase
2723:6–14 ng/mL
2717:2100 L/day
2697:2100 L/day
2694:1.7 mg/day
2666:180 μg/day
2646:100 μg/day
2607:1200 L/day
2604:240 μg/day
2601:250 μg/day
2587:1200 L/day
2568:6–60 pg/mL
2562:1610 L/day
2542:2200 L/day
2539:150 μg/day
2536:260 μg/day
2522:2200 L/day
2516:110 μg/day
2491:190 μg/day
2470:2000 L/day
2467:2.8 mg/day
2464:3.2 mg/day
2413:1600 L/day
2386:2050 L/day
2383:110 μg/day
2380:150 μg/day
2356:6.2 mg/day
2353:6.5 mg/day
2332:2200 L/day
2329:1.6 mg/day
2326:2.8 mg/day
2174:Estradiol,
2098:zoledronate
2076:target the
2051:carotenoids
2047:isoprenoids
1997:epoxidation
1962:antibiotics
1940:cyclization
1831:cyclopamine
1819:veratramine
1815:cyclopamine
1772:Norsteroids
1691:Androstanes
1652:Cholestanes
1631:Cyclopamine
1621:secosteroid
1499:cholesterol
1493:alfatradiol
1388:endometrium
1354:Aldosterone
1271:By function
1168:ecdysterone
1056:cholesterol
1025:ergosterols
1015:framework.
998:prokaryotes
754:Unsaturated
674:hydrocarbon
670:cholesterol
625:Cholesterol
574:bond orders
552:phytosterol
449:Cholic acid
431:sex hormone
408:side chains
392:cyclohexane
384:fused rings
309:hydrocarbon
230:cyclohexane
196:cholesterol
182:cyclization
131:cholesterol
118:that alter
20870:Categories
20658:Zanoterone
20623:Lonaprisan
20610:Steroidal:
20584:Naringenin
20574:Kaempferol
20554:Vilaprisan
20484:Asoprisnil
20466:Steroidal:
20439:ORG-201745
20419:Tanaproget
20314:Trestolone
20251:Nandrolone
20246:Mibolerone
20181:Dienedione
20171:Bolandione
20132:Tosagestin
20107:Oxendolone
20092:Norgestrel
20043:Metynodiol
20013:Gestrinone
19988:Ethynerone
19885:Oxogestone
19750:Mometasone
19640:Gestaclone
19605:Flugestone
19560:Clogestone
19500:Anagestone
19289:modulators
19189:Nimodipine
19184:Nifedipine
19174:Finerenone
19169:Felodipine
19154:Benidipine
19144:Amlodipine
19124:Vamorolone
19064:RO-14-9012
18979:Eplerenone
18959:Dicirenone
18896:Steroidal:
18873:Prednisone
18841:Prednazate
18824:Mometasone
18657:modulators
18573:IONIS-GCCR
18479:Miconazole
18414:Asoprisnil
18381:Mapracorat
18371:Dagrocorat
18249:Flugestone
18142:Cortivazol
18137:Cortisuzol
18127:Triclonide
18019:Fluazacort
17960:Budesonide
17930:Vamorolone
17894:Timobesone
17882:Ticabesone
17877:Rimexolone
17831:Mometasone
17712:Fluocortin
17557:Clobetasol
17472:Tixocortol
17462:Resocortol
17433:Prednisone
17401:Prednazate
17273:Etiprednol
17166:Cloprednol
17043:modulators
16901:Tectoridin
16881:Raloxifene
16856:Oleuropein
16703:Trilostane
16648:Prochloraz
16608:MDL-101906
16603:ICI-164384
16490:Trioxifene
16485:Toremifene
16455:Raloxifene
16440:Panomifene
16435:Ospemifene
16400:Nafoxidine
16290:Cyclofenil
16245:Arzoxifene
16225:Acolbifene
16157:phthalates
16125:bisphenols
16097:miroestrol
16001:methiocarb
15989:endosulfan
15977:Pesticides
15949:enterodiol
15930:tectoridin
15910:penduletin
15906:naringenin
15890:kaempferol
15806:Flavonoids
15800:psoralidin
15796:coumestrol
15792:Coumestans
15756:dianethole
15709:WAY-214156
15699:WAY-200070
15694:WAY-169916
15689:WAY-166818
15659:SKF-82,958
15624:Phenestrol
15604:Methestrol
15589:-Hexestrol
15581:-Butestrol
15462:Dienestrol
15442:Carbestrol
15427:Bifluranol
15422:Benzestrol
15367:Quinestrol
15317:Nilestriol
15159:Estrazinol
15092:Epimestrol
15082:-Estradiol
15064:Cyclotriol
15002:nandrolone
14977:Almestrone
14812:7-Oxo-DHEA
14724:Steroidal:
14696:modulators
14590:-ornithine
14533:gadolinium
14382:Prochloraz
14377:Phenothrin
14357:Nilutamide
14328:Methiocarb
14248:Endosulfan
14213:Cioteronel
14208:Cimetidine
14198:BMS-641988
14193:BMS-570511
14188:BMS-501949
14162:Bisphenols
14117:Antarlides
14093:Zanoterone
14028:Oxendolone
13973:Ludaterone
13963:Galeterone
13913:Dicirenone
13810:Steroidal:
13776:Steroidal:
13769:Vosilasarm
13664:GSK2881078
13619:AC-262,536
13578:Trilostane
13486:Norgestrel
13435:Gestrinone
13403:Δ-Tibolone
13286:Mibolerone
13236:Stanozolol
13189:Metenolone
12966:Trenbolone
12925:Nandrolone
12875:Dienedione
12799:Stenbolone
12760:Mesabolone
12612:Silandrone
12607:Quinbolone
12602:Plomestane
12597:Formestane
12592:Exemestane
12514:Atamestane
12411:modulators
12336:nucleotide
12120:Bile acids
12096:Terpenoids
11927:vitamin Bs
11910:Cobalamins
11838:glucogenic
11826:polyamines
11786:Homoserine
11658:Glyoxylate
11551:Inositol-P
11346:Amino acid
11286:feeders to
11114:elongation
11069:Glyoxylate
11058:acid cycle
10984:Metabolism
10660:Glycolysis
10593:metabolism
10591:Nucleotide
10581:Urea cycle
10562:Amino acid
10551:Catabolism
10494:Glycolysis
10437:Glycolysis
10420:metabolism
10380:catabolism
10376:Metabolism
10304:Calcitriol
10237:Pheromones
10081:Pregnanes:
9260:Precursors
9249:Endogenous
9198:Ergosterol
9178:Fecosterol
9148:Sitosterol
9110:Sitosterol
9028:Zymosterol
9006:Zymostenol
9001:Zymosterol
8994:Zymosterol
8974:Lanosterol
8967:Lanosterol
8855:Carotenoid
8737:Acetyl-CoA
8554:Zeaxanthin
8398:Lanosterol
8345:Sitosterol
8340:Sitostanol
8216:Paclitaxel
8123:Monocyclic
8010:Ascaridole
8005:Eucalyptol
7958:Hinokitiol
7932:Monocyclic
7802:Monocyclic
7669:terpenoids
7622:Azasteroid
7601:Norsteroid
7557:Cholestane
7322:Androstene
7315:Androstane
7274:Estradiene
7105:biomimetic
6976:1 December
6924:1 December
6140:: 106436.
5314:(6): 313.
4934:: 364–81.
4537:: 111189.
4237:Endocr Rev
4047:16 October
3742:Greep 2013
3606:(2): 771.
3471:Harper D.
3235:References
3155:Odd Hassel
3145:lanosterol
3051:Norgestrel
3005:sapogenins
2982:Precursors
2956:precursors
2941:catabolism
2939:Microbial
2899:adsorption
2895:extraction
2867:conjugated
2714:24 mg/day
2711:25 mg/day
2672:146 L/day
2652:146 L/day
2627:910 L/day
2584:80 μg/day
2581:90 μg/day
2556:40 μg/day
2519:80 μg/day
2497:500 L/day
2494:60 μg/day
2440:167 L/day
2434:80 μg/day
2410:50 μg/day
2407:60 μg/day
2359:950 L/day
2163:Cortisol,
2122:See also:
2067:ergosterol
2063:lanosterol
2024:acetyl-CoA
1970:acetyl-CoA
1932:lanosterol
1920:lanosterol
1865:signalling
1849:smoothened
1708:Estradiol
1613:(vitamin D
1588:March 2017
1547:calcitriol
1503:ergosterol
1459:Bile acids
1239:) and the
1233:metabolism
1156:vertebrate
1124:Solanaceae
1100:lanosterol
1096:zymosterol
1067:in fungi.
1065:ergosterol
1041:pathogenic
1031:, such as
1006:eukaryotes
981:Eukaryotic
926:eukaryotes
905:March 2017
735:The name "
686:androstane
651:cholestane
639:precursor.
611:lanosterol
562:expansions
495:Lanosterol
343:See also:
307:"slab" of
254:cholestane
186:triterpene
170:lanosterol
145:, and the
103:with four
20708:ZM-172406
20703:ZM-150271
20693:LG-121046
20688:LG-120830
20683:LG-100128
20678:LG-100127
20673:LG-001447
20643:ORG-33628
20638:ORG-31806
20633:ORG-31710
20579:LG-120920
20559:ZK-137316
20539:RMI-12936
20534:ORG-33628
20529:ORG-31710
20504:LG-120838
20434:ORG-47241
20424:ZM-182345
20414:RWJ-60130
20409:RWJ-49853
20404:RWJ-26819
20394:LG-100128
20354:Prorenone
20334:Canrenone
20309:Trendione
20186:Dienolone
20161:Bolandiol
20008:Gestodene
19998:Etynodiol
19966:Dienogest
19951:Cingestol
19815:Amadinone
19760:Osaterone
19710:Megestrol
19485:Algestone
19435:Ro 6-3129
19375:Diosgenin
19209:SM-368229
19059:Prorenone
19024:Mexrenone
18984:Gestodene
18800:Cortisone
18509:ORG-34850
18499:ORG-34116
18269:Gestodene
18174:Oxisopred
18152:Naflocort
18100:Tralonide
17467:Tipredane
17367:Medrysone
17234:Deprodone
17222:Cortisone
17149:Amebucort
16896:Tamoxifen
16876:Quercetin
16816:Genistein
16796:Estradiol
16780:o',p'-DDE
16683:ZK-191703
16678:ZK-164015
16638:Phenytoin
16536:(R,R)-THC
16475:Tamoxifen
16450:Promensil
16375:LY-117018
16350:Idoxifene
16345:ICI-55548
16330:Femarelle
16315:Endoxifen
16275:Clomifene
16031:diosgenin
16027:digitalis
16023:digitoxin
16013:triclosan
15993:fenarimol
15926:quercetin
15902:myricetin
15898:mirificin
15886:glycitein
15878:genistein
15874:glabridin
15834:calycosin
15822:baicalein
15778:phloretin
15734:ZK-283197
15594:Mestilbol
15556:Hexestrol
15531:Fenestrel
15506:Efavirenz
15437:Butestrol
15392:2,8-DHHHC
15387:(S,S)-THC
15382:(R,R)-THC
15337:Pentolame
15332:Orestrate
15307:Moxestrol
15297:Mestranol
15262:Etynodiol
15122:Estradiol
15097:Equilenin
15059:Cyclodiol
15017:Bolandiol
14576:-arginine
14561:Estradiol
14541:strontium
14537:magnesium
14525:aluminium
14492:YM-175735
14427:Ro 5-2537
14422:Ro 2-7239
14372:PF-998425
14367:Pentomone
14308:LG-120907
14268:Flutamide
14263:Fenarimol
14203:CH5137291
14142:Bakuchiol
14078:Topterone
14043:Prorenone
14018:Osaterone
14013:Nordinone
13998:Mexrenone
13918:Dienogest
13868:Canrenone
13789:TFM-4AS-1
13729:ORM-11984
13669:GSK-4336A
13659:GLPG-0492
13583:ZM-182345
13430:Gestodene
13418:Etynodiol
13174:Furazabol
13065:Enestebol
12993:Trendione
12954:Oxabolone
12880:Dienolone
12853:Bolandiol
12782:Nisterime
12536:Clostebol
12519:Boldenone
12105:vitamin A
12089:backbones
12087:Terpenoid
11982:Cofactors
11974:vitamin E
11964:vitamin K
11952:vitamin A
11947:Retinoids
11939:vitamin D
11914:vitamin B
11879:vitamin C
11874:Ascorbate
11867:histidine
11854:Shikimate
11833:Ketogenic
11800:Glutamate
11777:Aspartate
11729:glutarate
11644:Pentose-P
11628:Succinate
11619:Propionyl
11612:Tetrose-P
11605:Pentose-P
11501:Glycosyl-
11441:Shikimate
11389:Lipolysis
11331:Oxidative
11288:gluconeo-
11230:oxylation
11211:Gluconeo-
11168:genolysis
11151:oxidation
11127:oxidation
11099:synthesis
11043:phosphate
10833:lipolysis
10640:anabolism
10384:anabolism
10289:Vitamin D
9728:Estradiol
9720:Estranes:
9712:Estrogens
9514:Androgens
9388:Cortisone
9183:Episterol
8626:Synthesis
8482:Carotenes
8377:Ecdysones
8181:Forskolin
8169:Tricyclic
8156:Epimanool
8081:Nootkatin
8078:Muurolene
8070:Juniperol
8062:Chanootin
8043:Bisabolol
7974:Carvacrol
7814:Terpinene
7716:(4 rings)
7663:Types of
7538:Bile acid
6303:: 47–65.
6051:2002-4436
5722:1663-9812
5555:890107246
5190:Ochsner J
4559:231776716
4317:1 October
4291:1 October
3812:CC BY 4.0
3800:257943362
3600:Molecules
3208:Pheromone
3141:cortisone
3083:Chemistry
3045:(e.g. 13-
3023:diosgenin
2883:isolation
2691:2 mg/day
2621:6 μg/day
2574:Estradiol
2398:Estradiol
2288:Metabolic
2146:estrogens
2142:androgens
2116:enzymatic
1958:organisms
1845:hoshinota
1811:corn lily
1763:vitamin D
1678:Pregnanes
1535:Vitamin D
1426:Estradiol
1420:Estrogens
1403:Androgens
1396:pregnancy
1211:estrogens
1207:androgens
1122:found in
1120:alkaloids
1106:utilizes
1072:vitamin D
961:talk page
453:bile acid
266:vitamin D
213:'solid'.
135:estradiol
122:; and as
85:lanostane
20876:Steroids
20825:See also
20746:Agonists
20569:Apigenin
20524:ORF-9326
20519:ORF-9371
20431:Unknown:
20127:Tigestol
20122:Tibolone
19880:ORG-2058
19420:DU-41165
19415:DU-41164
19310:Agonists
19225:See also
19134:ZK-97894
19129:ZK-91587
19114:Tibolone
19094:SC-27169
19089:SC-19886
19069:RU-26752
18773:Cortisol
18678:Agonists
18593:See also
18539:Tibolone
18469:LLY-2707
18344:GSK-9027
18339:AZD-5423
18239:DU-41165
18184:RU-28362
18179:RU-26988
17668:Dimesone
17195:Cortisol
17065:Agonists
16974:See also
16776:p,p'-DDT
16767:Daidzein
16757:Atrazine
16730:Agonists
16658:RU-58668
16653:RU-39411
16500:U-11555A
16495:TZE-5323
16240:Anordrin
16235:Anordiol
16168:agnuside
16145:parabens
15985:dieldrin
15957:nyasol (
15922:puerarin
15918:prunetin
15882:genistin
15870:glabrene
15842:daidzein
15838:catechin
15826:baicalin
15818:apigenin
15748:anethole
15536:FERb 033
15372:Tibolone
15357:RU-16117
15342:Prodiame
15277:Hippulin
15272:Hexolame
15117:Estetrol
15027:Butolame
14717:Agonists
14627:See also
14514:Agonists
14487:YM-92088
14452:RU-58841
14447:RU-58642
14442:RU-57073
14437:RU-56187
14432:RU-22930
14362:ONC1-13B
14313:LGD-1331
14238:Dieldrin
14232:p,p’-DDE
14137:AZD-3514
14122:Arabilin
14053:RU-15328
13993:Metogest
13928:DU-41165
13764:S-101479
13744:RU-59063
13699:LGD-4033
13694:LGD-3303
13684:LGD-2226
13674:GSK-8698
13573:Drupanol
13568:Cl-4AS-1
13508:Tibolone
12689:Bolazine
12432:Agonists
12324:cofactor
12203:Steroids
12143:Acyl-CoA
12127:Glycero-
12031:Proteins
11994:minerals
11989:Vitamins
11960:Quinones
11896:pigments
11821:Creatine
11814:Arginine
11718:Succinyl
11672:Pyruvate
11591:Glycerol
11584:Triose-P
11577:Hexose-P
11529:multiple
11226:Pyruvate
11017:fixation
10756:Nonhuman
10741:O-linked
10736:N-linked
10528:Specific
10015:5α-DHDOC
9723:Estetrol
9491:Cortisol
9383:Cortisol
9252:steroids
9160:instead.
9101:Nonhuman
9093:instead.
8957:Squalene
8868:Phytoene
8833:Geranyl-
8525:Phytoene
8510:Lycopene
8411:Squalane
8403:Saponins
8314:Steroids
8176:Cembrene
8153:-Abienol
8144:Bicyclic
8048:Cadinene
7983:Bicyclic
7949:p-Cymene
7923:Linalool
7908:Geraniol
7859:Sabinene
7849:Camphene
7828:Bicyclic
7809:Limonene
7793:Myrcenes
7734:Isoprene
7714:Steroids
7705:Iridoids
7673:isoprene
7665:terpenes
7448:Pregnene
7441:Pregnane
7133:24342885
7099:16351060
7020:Archived
6970:Archived
6944:Archived
6918:Archived
6892:Archived
6866:Archived
6840:Archived
6814:Archived
6769:13411462
6535:Archived
6508:27 March
6502:Archived
6479:12372848
6438:16749856
6403:16872679
6368:20671993
6342:: 1–11.
6317:15012203
6274:Archived
6269:androgen
6209:Archived
6191:16759697
6156:38035948
6108:20 April
6102:Archived
6090:22217824
6002:17062705
5967:21267417
5828:27523830
5820:14517367
5778:12735695
5740:30258364
5706:: 1027.
5681:16621811
5624:27672740
5489:92690863
5436:Archived
5381:Archived
5363:20424788
5328:10715364
5291:11 April
5285:Archived
5230:Archived
5212:24940130
5121:12946402
5015:21531832
4958:20333205
4909:37959511
4901:12519197
4865:34131078
4808:cite web
4778:34131078
4719:Archived
4689:Archived
4551:33539964
4516:32203405
4467:35611324
4404:Steroids
4381:13167092
4311:Archived
4309:. 2022.
4285:Archived
4283:. 2022.
4267:21051590
4041:Archived
3935:Archived
3814:license.
3632:36677830
3573:Archived
3519:Archived
3487:19 March
3481:Archived
3417:16236742
3344:Archived
3289:Archived
3285:97612891
3176:See also
3170:squalene
3109:terpenes
2881:Steroid
2780:pyruvate
2758:Sources:
2184:placenta
2130:pathways
2059:squalene
2043:terpenes
2039:isoprene
1954:anabolic
1947:squalene
1916:squalene
1853:hedgehog
1840:. e.g.,
1835:Okinawan
1827:cyclopia
1704:Estranes
1665:Cholanes
1643:Example
1513:saponins
1461:such as
1443:such as
1333:Cortisol
1166:such as
1142:and the
1132:Veratrum
1013:hopanoid
918:bacteria
851:compound
843:pregnane
772:hydrogen
703:cortisol
682:pregnane
678:skeleton
396:perhydro
305:nonpolar
189:squalene
43:reviewed
18:Steroids
20589:PRA-910
20389:LG-2527
20364:SC-8109
20297:(e.g.,
20280:RU-2309
20258:(e.g.,
20065:(e.g.,
20025:(e.g.,
19956:Danazol
19159:BR-4628
19079:SC-8109
18429:C113176
18424:C108297
18314:RU-2309
18224:Danazol
16946:Unknown
16922:Estriol
16826:GPER-L2
16821:GPER-L1
16505:U-11634
16380:Menerba
16370:LN-2299
16365:LN-1643
16340:GW-7604
16295:D-15413
16127:(e.g.,
16119:(e.g.,
16105:(e.g.,
16089:Steroid
16061:(e.g.,
16043:(e.g.,
16021:(e.g.,
15979:(e.g.,
15971:cadmium
15969:(e.g.,
15947:(e.g.,
15945:Lignans
15846:daidzin
15810:7,8-DHF
15808:(incl.
15794:(e.g.,
15772:(e.g.,
15654:SERBA-2
15649:SC-4289
15644:SC-3296
15551:GTx-758
15447:D-15414
15397:β-LGND1
15347:Prolame
15196:Estrone
15164:Estriol
15102:Equilin
14984:(e.g.,
14897:16α-LE2
14583:-lysine
14571:(incl.
14529:calcium
14523:(incl.
14521:Cations
14318:Linuron
14258:EPI-001
14164:(e.g.,
13953:EM-6537
13948:EM-5855
13943:EM-5854
13938:EM-4350
13784:MK-0773
13779:EM-9017
13759:S-40503
13614:ACP-105
13609:198RL26
13474:(e.g.,
13447:(e.g.,
13356:Danazol
13306:RU-2309
13246:Bolenol
12340:protein
12320:vitamin
12022:Nucleic
11925:Various
11807:proline
11761:Alanine
11727:α-Keto-
11704:acetate
11695:Citrate
11679:Lactate
11535:glycans
11443:pathway
11363:shuttle
11361:Citrate
11290:genesis
11273:genesis
11228:decarb-
11213:genesis
11183:genesis
11045:pathway
11041:Pentose
10896:Ketosis
10508:Ethanol
10391:General
10316:Others:
9955:(e.g.,
9825:Others:
9738:Estriol
9733:Estrone
8909:CDP-MEP
8775:Acetone
8757:HMG-CoA
8752:HMB-CoA
8729:HMG-CoA
8708:steroid
8663:(DMAPP)
8393:Betulin
8191:Pimarol
8188:Pimaral
8135:Retinal
8130:Retinol
8099:Acyclic
8058:Cedrene
8053:Cadinol
7995:Borneol
7990:Camphor
7944:Menthol
7918:Halomon
7886:Acyclic
7854:Thujene
7788:Ocimene
7781:Acyclic
7533:Cholane
7269:Estrene
7262:Estrane
7225:Steroid
7141:6090764
7090:2575671
6599:Bibcode
6359:2910408
6010:9734002
5958:3023269
5916:4019443
5908:7791529
5873:7023367
5731:6144938
5672:1447442
5632:2354209
5408:Arkivoc
5203:4052587
5101:Bibcode
5006:3131620
4985:Bibcode
4949:2817430
4856:8237579
4769:8237579
4665:2606099
4618:Bibcode
4507:7881526
4458:9123281
4389:8408420
4258:3365799
4162:2606099
4121:2606099
3982:2606099
3931:2606099
3889:2606099
3847:2606099
3701:(D).1,2
3665:20 June
3623:9864676
3425:5744727
3330:2606099
3055:methoxy
3015:, used
2974:and/or
2847:oxidase
2509:Estrone
2371:Estrone
2283:Gonadal
2229:de novo
2224:enzymes
2218:in the
2212:neurons
2176:estrone
2082:statins
2034:(IPP).
1980:(IPP).
1966:statins
1942:of the
1914:(GPP),
1843:Terpios
1813:ingest
1800:acyclic
1390:of the
1259:natural
989:During
922:archaea
595:sterols
585:in the
572:in the
433:and an
349:Sterane
258:cutting
246:Sterols
211:stereos
184:of the
167:sterols
163:animals
97:steroid
19380:P1-185
18563:Others
18358:SEGRMs
16841:Niacin
16836:Kepone
16693:ERX-11
16663:SS1020
16571:ERB-88
16566:ERA-90
16470:SS1010
16395:MRL-37
15760:dianol
15729:ERB-79
15724:ERA-45
15719:ERB-26
15452:DCW234
15407:AC-186
15074:DHEA-S
15006:esters
14990:esters
14842:8β-VE2
14506:GPRC6A
14482:YM-580
14412:RD-162
14303:LG-105
13654:FTBU-1
12241:Major
12194:&
12159:Glyco-
12099:&
12071:Acetyl
12041:&
11992:&
11968:&
11865:&
11824:&
11805:&
11793:lysine
11791:&
11738:bodies
11736:Ketone
11711:Malate
11702:Oxalo-
11686:Acetyl
11635:Acetyl
11561:&
11544:sugars
11542:Simple
11533:&
11531:sugars
11525:Double
11196:Glyco-
11181:Glyco-
11166:Glyco-
11056:Citric
11028:Photo-
11015:Carbon
10418:Energy
10281:Others
9282:20α,22
9081:20α,22
8919:HMB-PP
8904:CDP-ME
8585:(many)
8564:Lutein
8415:Acids
8106:Phytol
7964:Thymol
7898:Citral
7864:Carene
7835:Pinene
7748:Prenol
7695:forms)
7675:units)
7671:(# of
7243:Gonane
7165:
7139:
7131:
7097:
7087:
7051:
7026:10 May
7004:
6767:
6757:
6697:
6629:987752
6627:
6620:170056
6617:
6568:
6541:10 May
6477:
6436:
6401:
6366:
6356:
6315:
6250:
6189:
6154:
6098:112729
6096:
6088:
6049:
6008:
6000:
5965:
5955:
5914:
5906:
5888:Lipids
5871:
5826:
5818:
5776:
5738:
5728:
5720:
5679:
5669:
5630:
5622:
5576:
5553:
5543:
5487:
5477:
5442:20 May
5387:20 May
5361:
5326:
5259:
5210:
5200:
5167:
5142:
5119:
5074:
5036:
5013:
5003:
4956:
4946:
4907:
4899:
4863:
4853:
4839:(25).
4798:17 May
4776:
4766:
4752:(25).
4663:
4588:
4557:
4549:
4514:
4504:
4465:
4455:
4387:
4379:
4265:
4255:
4195:
4160:
4119:
4078:
4015:
3980:
3929:
3887:
3845:
3798:
3784:: 29.
3725:
3692:
3656:
3630:
3620:
3423:
3415:
3378:
3350:10 May
3328:
3283:
3143:, and
3125:, and
3113:1950 (
3081:1927 (
3063:phenol
3009:Syntex
2954:(i.e.
2905:, and
2835:CYP3A4
2735:Notes:
2451:Women
2308:units
2301:units
2275:phase
2207:cells.
2192:testes
2144:, and
2096:(like
2092:, and
2084:(like
1928:plants
1881:lipids
1640:Class
1545:, and
1392:uterus
1213:, and
1184:plaque
1160:insect
1150:Animal
1138:, the
1098:, and
1019:Fungal
924:, and
814:" for
806:" for
798:" for
790:" for
763:locant
748:carbon
741:oxygen
709:has a
672:-like
497:, the
380:carbon
376:Gonane
358:Gonane
345:Gonane
323:and a
317:5α-DHP
226:carbon
222:gonane
209:' and
203:chole-
161:, and
159:plants
99:is an
20499:J1042
20453:SPRMs
20448:Mixed
18353:Mixed
16917:CCL18
16791:Equol
16673:ZB716
16643:PHTPP
16510:Y-134
16187:SERMs
16182:Mixed
15862:equol
15744:Anise
15573:M2613
14170:BFDGE
14166:BADGE
14112:AA560
13794:YK-11
13704:LY305
13594:SARMs
12210:Endo-
12175:Waxes
12152:acids
12150:Fatty
12024:acids
11903:Hemes
11887:δ-ALA
11863:acids
11835:&
11802:group
11788:group
11779:group
11747:chain
11518:acids
11516:Sugar
11503:ation
11271:Keto-
11258:lysis
11256:Keto-
11198:lysis
11110:Fatty
11095:Fatty
11084:cycle
11071:cycle
10914:Other
10874:Other
10649:Human
10530:paths
10169:THDOC
10124:DHDOC
9152:More
9057:From
8929:DMAPP
8914:MEcPP
8796:DMAPP
8657:(IPP)
8474:) (8)
8386:Other
7693:trans
7137:S2CID
6765:S2CID
6094:S2CID
6035:(1).
6006:S2CID
5912:S2CID
5835:(PDF)
5824:S2CID
5796:(PDF)
5628:S2CID
5485:S2CID
4905:S2CID
4555:S2CID
4385:S2CID
3796:S2CID
3774:(PDF)
3421:S2CID
3292:(PDF)
3281:S2CID
3260:(PDF)
3047:alkyl
3041:from
3003:, or
2911:LC-MS
2839:liver
2737:"The
2278:Blood
2210:Some
2180:ovary
2074:drugs
1829:from
1784:homos
1780:norma
1778:, L.
1738:alkyl
1266:Types
1245:renal
1114:Plant
855:alkyl
835:vowel
810:and "
794:and "
633:lipid
386:in a
313:polar
176:) or
155:fungi
128:lipid
105:fused
89:IUPAC
20733:PAQR
16937:MIBE
16932:G-36
16927:G-15
16861:PCBs
16718:GPER
16628:MIBE
16161:PCBs
16153:PHBA
16149:PBBs
15997:HPTE
15854:EGCG
15752:anol
15587:meso
15579:meso
15069:DHEA
15004:and
14988:and
14602:SHBG
14545:zinc
14243:DIMP
13858:BOMT
13754:S-23
13644:DTIB
12338:and
12322:and
12073:-CoA
12008:PRPP
11894:Bile
11720:-CoA
11688:-CoA
11637:-CoA
11621:-CoA
11149:beta
11125:Beta
11112:acid
11097:acid
11082:Urea
10638:and
10219:DHEA
9853:DHEA
9567:DHEA
9158:here
9156:see
9091:here
9089:See
8894:DOXP
8706:and
7841:and
7774:)(2)
7691:and
7667:and
7163:ISBN
7129:PMID
7095:PMID
7049:ISBN
7028:2014
7002:ISBN
6978:2013
6952:2013
6926:2013
6900:2013
6874:2013
6848:2013
6822:2013
6755:ISBN
6695:ISBN
6625:PMID
6566:ISBN
6543:2014
6510:2015
6475:PMID
6434:PMID
6399:PMID
6364:PMID
6340:2010
6313:PMID
6282:2024
6248:ISBN
6217:2024
6187:PMID
6152:PMID
6110:2018
6086:PMID
6047:ISSN
5998:PMID
5963:PMID
5904:PMID
5869:PMID
5816:PMID
5774:PMID
5736:PMID
5718:ISSN
5677:PMID
5620:PMID
5574:ISBN
5551:OCLC
5541:ISBN
5475:ISBN
5444:2014
5412:2007
5389:2014
5359:PMID
5324:PMID
5293:2022
5257:ISBN
5238:2024
5208:PMID
5165:ISBN
5140:ISBN
5117:PMID
5072:ISBN
5034:ISBN
5011:PMID
4954:PMID
4897:PMID
4861:PMID
4814:link
4800:2024
4774:PMID
4727:2024
4697:2024
4661:PMID
4586:ISBN
4547:PMID
4512:PMID
4463:PMID
4377:PMID
4319:2023
4293:2023
4263:PMID
4193:ISBN
4158:PMID
4117:PMID
4076:ISBN
4049:2023
4013:ISBN
3978:PMID
3943:2024
3927:PMID
3885:PMID
3843:PMID
3723:ISBN
3690:ISBN
3667:2015
3654:ISBN
3628:PMID
3581:2023
3527:2023
3489:2023
3458:2006
3413:PMID
3376:ISBN
3352:2014
3326:PMID
3300:2012
3168:via
3153:and
3103:and
2991:The
2962:and
2843:bile
2817:and
2782:and
2313:Men
2304:Non-
2267:Sex
2216:glia
2214:and
2045:and
1918:and
1851:and
1807:ewes
1776:nor-
1750:seco
1601:MeSH
1515:and
1452:and
1446:DHEA
1356:, a
1335:, a
1235:and
1158:and
1126:and
1049:ERG6
1045:ERG3
1035:and
859:aryl
744:atom
627:, a
605:and
564:and
482:drug
451:, a
347:and
207:bile
137:and
20723:mPR
16891:STX
16811:G-1
16772:DDT
16593:III
16141:DDT
16139:),
16137:BPS
16133:BPF
16129:BPA
16029:),
15959:cis
15850:ECG
15080:ent
14228:DDT
13749:S-1
13739:R-1
12245:in
12064:MVA
12057:MEP
10986:map
10662:⇄
10503:ABE
10164:THB
10119:DHC
9168:To
9108:To
9062:to
8942:To
8924:IPP
8899:MEP
8794:to
8747:HMB
8727:to
8306:(6)
8289:(5)
8151:cis
8092:(4)
8031:(3)
7727:(1)
7689:cis
7121:doi
7085:PMC
7077:doi
7073:105
7041:doi
6792:doi
6747:doi
6724:doi
6687:doi
6659:doi
6615:PMC
6607:doi
6465:doi
6426:doi
6391:doi
6387:112
6354:PMC
6344:doi
6305:doi
6240:doi
6179:doi
6142:doi
6138:236
6078:doi
6037:doi
5990:doi
5953:PMC
5943:doi
5896:doi
5861:doi
5808:doi
5766:doi
5726:PMC
5708:doi
5667:PMC
5659:doi
5655:188
5610:doi
5606:140
5516:doi
5467:doi
5426:hdl
5416:doi
5351:doi
5316:doi
5198:PMC
5109:doi
5001:PMC
4993:doi
4944:PMC
4936:doi
4889:doi
4851:PMC
4841:doi
4837:118
4764:PMC
4754:doi
4750:118
4670:C=O
4653:doi
4649:186
4626:doi
4614:160
4578:doi
4539:doi
4535:525
4502:PMC
4494:doi
4453:PMC
4443:doi
4412:doi
4369:doi
4342:doi
4253:PMC
4245:doi
4185:doi
4150:doi
4146:186
4109:doi
4105:186
4068:doi
4005:doi
3970:doi
3966:186
3919:doi
3915:186
3877:doi
3873:186
3835:doi
3831:186
3786:doi
3618:PMC
3608:doi
3405:doi
3401:353
3318:doi
3314:186
3273:doi
2958:to
2943:of
2921:NMR
2855:PXR
2841:in
1798:of
1711:18
1698:19
1685:21
1672:24
1659:27
1583:.
1296:.
1134:),
1047:or
996:In
857:or
779:or
720:at
701:or
649:5α-
141:,
111:.
45:on
20872::
20301:,
20262:,
20069:,
19298:PR
18779:)
18666:MR
18575:Rx
17201:)
17052:GR
16778:,
16597:IV
16595:,
16591:,
16589:II
16587:,
16170:,
16159:,
16155:,
16151:,
16147:,
16143:,
16135:,
16131:,
16123:,
16109:,
16095:,
16081:,
16077:,
16073:,
16069:,
16065:,
16051:,
16047:,
16033:,
16011:,
16007:,
16003:,
15999:,
15995:,
15991:,
15987:,
15983:,
15955:,
15951:,
15932:,
15928:,
15924:,
15920:,
15916:,
15912:,
15908:,
15904:,
15900:,
15896:,
15892:,
15888:,
15884:,
15880:,
15876:,
15872:,
15868:,
15864:,
15860:,
15856:,
15852:,
15848:,
15844:,
15840:,
15836:,
15832:,
15828:,
15824:,
15820:,
15816:,
15812:,
15798:,
15784:,
15780:,
15776:,
15762:,
15758:,
15754:,
15750:,
15000:,
14996:,
14992:,
14705:ER
14585:,
14578:,
14543:,
14539:,
14535:,
14531:,
14527:,
14180:,
14176:,
14172:,
14168:,
13478:,
13133:)
12722:)
12623:)
12420:AR
12107:)
11976:)
11954:)
11941:)
11919:)
11916:12
11881:)
10835:,
10679:⇄
10496:→
10456:+
10447:→
10443:→
10439:→
10382:,
10378:,
10065:24
9959:,
9273:22
9072:22
7772:16
7768:10
7766:(C
7736:(C
7549:27
7525:24
7506:23
7460:;
7443::
7433:21
7414:20
7401:;
7334:;
7317::
7307:19
7281:;
7264::
7254:18
7235:17
7180:.
7157:.
7153:.
7135:.
7127:.
7117:10
7115:.
7093:.
7083:.
7071:.
7067:.
7047:.
6788:61
6786:.
6763:.
6753:.
6720:73
6718:.
6693:.
6671:^
6655:11
6653:.
6637:^
6623:.
6613:.
6605:.
6595:32
6593:.
6589:.
6551:^
6529:.
6518:^
6496:.
6473:.
6461:23
6459:.
6455:.
6432:.
6420:.
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6311:.
6301:50
6299:.
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