26:
1410:. Among its many other effects, the drug caused these cells to decrease their levels of 20-HETE in vitro; the addition of 20-HETE to these cultures rescued the cells from apoptosis. Isoliquiritigenin also inhibits the in vivo lung metastasis of MDA-MB-231 cell transplants while concurrently decreasing the tumor's levels of 20-HETE. The growth of MDA-MB-231 cells implanted into athymic nude female mice as well as the cells' production of a large variety of agents stimulating vascularization including vascular endothelial growth factor were inhibited by treating the mice with an inhibitor of 20-HETE production.
1166:(Cyp4a14(-/-) mice develop male-specific, androgen-dependent hypertension. This seemingly paradoxical result is due to the overexpression of Cyp4a12a; the knockout of Cyp4a14 (Cyp4a14 does not produce 20-HETE) leads to the overexpression of the 20-HETE-producing cytochrome, Cyp4a149(-/-), and consequent overproduction of 20-HETE. The model involves increased plasma androgens, increased vascular and urinary levels of 20-HETE, relief of hypertension by castration, and hypertension which is driven by excessive fluid reabsorption in the kidney's proximal tubule secondary to the overexpression of
269:
1490:
prostaglandin and thromboxane products. In addition, 20-HETE itself blocks prostaglandin and thromboxane metabolites from interacting with the thromboxane receptor. Both effects, i.e. replacement of prostaglandin and thromboxane production with platelet-inactive products and thromboxane A2 receptor blockade, are responsible for 20-HETE's platelet aggregation-inhibiting action. However, the platelet anti-aggregating activity of 20-HETE requires micromolar levels and therefore may be more of a pharmacological than physiological activity.
1237:=2.31); 1538 males and females from the Framingham Heart Study (Odds ratio=1.23); males but not females in 732 black Americans with hypertensive renal disease participating in the African American Study of Kidney Disease; males in a sample of 507 individuals in Japan and in the third MONICA (MONitoring trends and determinants In Cardiovascular disease survey of 1397 individuals the homozygous C8590C genotype to the homozygous T8590T genotype with odds ratios of 3.31 for all subjects, 4.30 for males 2.93 for women);
1260:(adjusted odds ratio of 1.50 in comparing homozygous and heterozygous C296T subjects to homozygous C286C subjects) in >2000 individuals taken from the Han Chinese population. The effect of the β296C>T single base pair substitution on baseline CYP411 transcriptional activity was not significant, suggesting that this polymorphism may not be the causal variant but instead may be in linkage disequilibrium with the causal variant. Regardless, this SNP may serve as a
1425:-binding sites, including those for miR-211, miR-125a-3p, miR-197, miR-1226, and miR-204'. Since these miRNA's reduce the translation of CYP4Z1, the expression of CYP4Z2P can bind these miRNAs to reduce their interference with CYP4Z1 and thereby increase the production of CYP4Z1 protein and perhaps 20-HETE; indeed, force expression of these 3'UTRs promoted in vitro tumor angiogenesis in breast cancer cells partly via miRNA-dependent activation of the
990:. While significantly less potent than thromboxane A2 in activating this receptor, studies on rat and human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the brain.
1506:. While significantly less potent than thromboxane A2 in activating this receptor, studies on human cerebral artery preparations indicate that increased blood flow through these arteries triggers production of 20-HETE which in turn binds to thromboxane receptors to constrict these vessels and thereby reduce their blood blow. Acting in the latter capacity, 20-HETE, it is proposed, functions as a mediator regulating blood flow to the human brain.
827:
activities to their prostaglandin and thromboxane precursors and since the 12-hydroxy and 11-hydroxy metabolites of 20-HETE may also be inactive, these metabolic pathways appear to function in inactivating 20-HETE with respect to the platelet system. However, the 20-hydroxy prostaglandin metabolites are able to contract rat aorta rings and thereby could contribute to the hypertensive actions of 20-HETE.
929:, angiotensin II. 20-HETE has a particularly complex interaction with the renin angiotensin system: angiotensin II stimulates the preglomerular microvessels of the rat kidney to produce 20-HETE; this production is required for angiotensin II to exert its full constrictor effects; and 20-HETE induces transcription of the enzyme which converts angiotensin I to angiotensin II, i.e.
708:, respectively. While many of the effects and diseases associated with the over- or under-expression, pharmacological inhibition, and single nucleotide or mutant variants of the cytochrome Ο-hydroxylases have been attributed to their impact on 20-HETE production, the influence of these alternate metabolic actions have frequently not been defined.
1182:(EETs). The model involves normal levels of 20-HETE, reduced expression of Cyp2c44, reduced levels of EETs, and deficiencies in kidney tubule absorption of sodium regulated by EETs, and the normalization of hypertensive blood pressure by increasing expression of Cyp2c44 by treating the mice with an inducer of its expression, an activator of
1138:
infused kidney, and produced a mean arterial pressure rise from 115 at baseline to 142 mm of mercury; this study indicates that the hypertensive versus hypotensive effects of 20-HETE depend not only on the organ of its production but also, with respect to the kidney, the site within the organ where it is produced.
1301:(i.e. ischemic stroke) in a study of 175 subjects with infarction compared to 246 control subjects in Japan, in 507 stroke patients compared to 487 age- and sex-matched 487 controls in India, and in males but not females in a study of 558 patients compared to 557 controls in China. The variant is associated with
879:
this organ and species. Coronary artery endothelial cells isolated from pigs incorporate 20-HETE primarily into the sn-2 position of phospholipids through a coenzyme A-dependent process. It is likely, although not yet shown, that these mouse and pig 20-HETE metabolizing pathways also occur in humans.
1137:
models) that had one kidney removed and then fed a high salt diet are hypertensive. Kidney medullary interstitial infusion of an inhibitor of 20-HETE production reduced the formation of 20-HETE in the outer medulla of the infused kidney, had no effect on the production of 20-HETE in the cortex of the
1092:
As indicated above, 20-HETE may raise blood pressure by constricting arterial blood vessels but also may lower blood pressure by promoting the loss of sodium and fluids in the kidneys. The effects of 20-HETE therefore are complex, as indicated in studies of the following animal models. Many of these
1475:
glioma cells in culture; since these cells could not be shown to produce 20-HETE, it was proposed that some other metabolite may by the inhibitor's targeted cytochrome enzymes was responsible for maintaining these cells growth. It is also possible that any such inhibitor has off-target effects that
469:
reaction. CYP450 enzymes belong to a superfamily which in humans is composed of at least 57 members and in mice at least 120 members. Among this superfamily, certain members of the CYP4A and CYP4F subfamilies in the CYP4 family are considered predominant cytochrome P450 enzymes that are responsible
1433:
and thereby stimulating the production of vascular endothelium growth factor and possibly other endothelium growth factors. Taken together, these pre-clinical studies suggest that 20-HETE made by one or more of the cited cytochrome P450 enzymes may contribute to the progression of breast cancer by
1216:
Human CYP4A11 has 72.69% amino acid identity with murine cyp4a14 and 73.02% identity with murine cyp4a10 suggesting that it plays a role in humans similar to that of cyp4a14 and/or cyp4a10 in mice. The association of hypertension with defective CYP4A11 in humans as indicated below seems to parallel
887:
20-HETE-synthesizing enzymes are widely distributed to liver, kidney, brain, lung, intestine and blood vessels. In most vascular systems, 20-HETE synthesizing activity is limited to vascular smooth muscle of small blood vessels with little or no such activity in the vessel's endothelial cells or in
1489:
to mediate and/or promote the ensuing platelet aggregation response to most stimuli. The platelets metabolize 20-HETE to the 20-hydroxy analogs of prostaglandin H2 and thromboxane A2, products that are essentially inactive in platelets, while consequently form less of the arachidonic acid-derived
1305:
in a study of 507 patients compared to 487 age- and sex-matched controls in India, in males but not females in a study of 234 patients compared to 248 control subjects in Japan, and in male but not female patients in Sweden enrolled in the cardiovascular cohort of the Malmo Diet and Cancer Study.
878:
reactions. These shortening pathways also are likely to serve in inactivating 20-HETE, although the initial product of this shortening pathway, 20-carboxy-HETE, dilates coronary microvessels in the pig heart and thereby could serve to antagonize the vasoconstrictor actions of 20-HETE, at least in
655:
inhibitors may act as perhaps unwanted side effects to increase the levels of 20-HETE. There are a variety of pharmacological agents which inhibit the synthesis of 20-HETE including various fatty acid analogs that compete reversibly with arachidonic acid for the substrate binding site in the CYP
532:
with the predominant 20-HETE-synthesizing enzymes being CYP4F2, which is the major 20-HETE producing enzyme in the human kidney, followed by CYP4A11. CYP4F3 is expressed as two distinct enzymes, CYP4F3A and CYP4F3B, due to alternative splicing of a single pre-mRNA precursor molecule; CYP4F3A is
1356:
dysfunction. A second homozygous enzyme-disabling mutation has been identified in CYP2U1, c.1A>C/p.Met1?, that is associated with <1% of hereditary spastic paraplegia sufferers. While the role of 20-HETE in these mutations has not been established, the reduction in 20-HETE production and
826:
of the hydroperoxy and hydroxyl residues at positions 11 and 12 in the eicosatetraenoic acids are predicted based on studies defining the chirality of the arachidonic metabolites made by these enzymes.) Since the prostaglandin and thromboxane metabolites of 20-HETE lack the platelet-stimulating
427:
including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. These vascular and kidney effects of 20-HETE have been shown to be responsible for regulating blood pressure and blood flow to specific organs in
1470:
While these studies suggest that CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 produce 20-HETE which in turn promotes the growth of the cited cancers in model systems and therefore may do so in the human cancers, this suggestion clearly needs much further study. For example, an inhibitor of 20-HETE
1293:
in comparing 249 patients with hypertension to 238 age-matched controls in Japan, the variant was not associated with hypertension. The maintenance of the lower blood pressure that followed diet-induced weight loss was more difficult for carriers of the Val433Met variant and may be related to
1240:
A study of 1501 participants recruited from the Tanno-Sobetsu Study found that the variant -845G in the promoter region of CYP411 (β845A is the predominant genotype) is associated with reduced transcription of CYP411 as well as with hypertension (odds ratio of homozygous and heterozygous -845G
1013:
rats that underwent balloon injury of the common carotid artery exhibited elevated levels of CYP4A enzyme immunostaining in the smooth muscle of the injured arteries as well as elevated levels of 20-HETE in the injured arteries. Inhibition of 20-HETE production by two different agents greatly
1466:
Messenger RNAs for CYP4A11, CYP4A22, CYP4F2, and/or CYP4F3 are more highly expressed in ovary, colon, thyroid, lung, ovary, cancers compared to their normal tissue counterparts; in ovarian cancer, this higher expression is associated with an increased level of CYP4F2 protein expression and an
1093:
models appear relevant to hypertension in humans in that they parallel the human disease, i.e. men have higher rates of hypertension than women, and women with increased levels of androgens (e.g. postmenopausal women and women with polycystic ovarian disease) and higher rates of hypertension.
557:
In mice, the only 20-HETE- and 19-HETE-producing enzymes of the Cyp4a subfamily are two extensively homologous ones, Cyp4a12a and Cyp4a12b; Cyp4a12a is expressed in the male kidney in an androgen hormone-dependent manner. In rats, Cyp4a1, Cyp4a2, Cyp4a3, and Cyp4a8 make 20-HETE. The tissue
545:, the only member of the human CYP2U subfamily, is highly expressed in brain and thymus and to lesser extents in numerous other tissues such as kidney, lung and heart. CYP2U1 protein is also highly expressed, compared to several other cytochrome P450 enzymes, in malignant breast tissue; the
1173:
Mice depleted of Cyp4a10 maintain normal blood pressure on a low salt diet but become hypertensive on normal or high salt diets; this paradoxical result appears due to a decrease in kidney levels of Cyp2C44 caused by the loss of Cyp4a10. Cyp2C44 metabolizes arachidonic acid a family of
1228:
rs1126742 variant of CYP4A11 switches thymidine to cytosine at nucleotide 8590 and leads to a phenylalanine-to-serine substitution at amino acid 434); this F434S variant has significantly reduced ability to Ο-oxidize arachidonic acid to 20-HETE and has been associated with
1125:
that in turn stimulates the CYp4A/20-HETE pathway. Non-selective and non-selective inhibitors of CYP4A and 20-HETE production reduce hypertension in this model. The hypertension in this model is more severe in male rats and appears to be mediated at least in part by
1272:
The T allele at rs2108622, which has been designated as CYP4F2*3 in the Human CYP Allele
Nomenclature Database by the Pharmacogene Variation Consortium, produces the CYP4F2 enzyme with methionine residue instead of valine at position 433 (the Val433Met variant), a
993:
These vasoconstrictor effects of 20-HETE can reduce blood flow to specific parts of the body, not only to brain (see previous paragraph) but also to kidney, liver, heart and other organs, as well as to portions of these organs; they can also contribute to systemic
1450:
cell line U251 and, when forced to overexpress CYP4Z1 by gene transfection, overproduced 20-HETE and exhibited a dramatically increased rate of growth that was blocked by inhibiting the cells from producing 20-HETE. A similar set of findings was found with human
1018:
hyperplasia and vascular remodeling that occurred after balloon injury. The studies suggest that the increase in expression of CYP4A and production of 20-HETE contribute to vascular intima growth, remolding, and thereby healing of injured rat carotid arteries.
975:; this inhibits the ability of eNOS to become activated. The endothelial cells become dysfunctional in exhibiting decreased ability to produce the vasodilating agent, nitric oxide, and in containing elevated levels of a potentially injurious oxygen radical,
432:; genetic and preclinical studies suggest that 20-HETE may similarly regulate blood pressure and contribute to the development of stroke and heart attacks. Additionally the loss of its production appears to be one cause of the human neurological disease,
2183:
Thomas RD, Green MR, Wilson C, Weckle AL, Duanmu Z, Kocarek TA, et al. (2006). "Cytochrome P450 expression and metabolic activation of cooked food mutagen 2-amino-1-methyl-6-phenylimidazo4,5-bpyridine (PhIP) in MCF10A breast epithelial cells".
4966:
Tatarunas V, Jankauskiene L, Kupstyte N, Skipskis V, Gustiene O, Grybauskas P, et al. (2014). "The role of clinical parameters and of CYP2C19 G681 and CYP4F2 G1347A polymorphisms on platelet reactivity during dual antiplatelet therapy".
1484:
20-HETE inhibits the aggregation of human platelets by competing with arachidonic acid for the enzymes that produce prostaglandin H2 and thromboxane A2. These products are formed in response to platelet stimulation and then act through the
5195:
Li Y, Zhao H, Wang Y, Zheng H, Yu W, Chai H, et al. (2013). "Isoliquiritigenin induces growth inhibition and apoptosis through downregulating arachidonic acid metabolic network and the deactivation of PI3K/Akt in human breast cancer".
5010:
Kim WY, Lee SJ, Min J, Oh KS, Kim DH, Kim HS, et al. (2018). "Identification of novel CYP4F2 genetic variants exhibiting decreased catalytic activity in the conversion of arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE)".
5242:
Zheng H, Li Y, Wang Y, Zhao H, Zhang J, Chai H, et al. (2014). "Downregulation of COX-2 and CYP 4A signaling by isoliquiritigenin inhibits human breast cancer metastasis through preventing anoikis resistance, migration and invasion".
1277:(1347C>T; NM_001082.5:c.1297G>A; p. Val433Met; rs2108622). This variant of the CYP4F2 enzyme has reduced capacity to metabolize arachidonic acid to 20-HETE but increased urinary excretion of 20-HETE. Studies found that:
1158:
mice overexpressing Cyp4a12 develop androgen-independent hypertension that is associated with increased levels of 20-HETE; this hypertension is fully reversible by treatment with a Cyp4a selective inhibitor of 20-HETE production.
696:, vascular responses, and other reactions. This metabolism-induced inactivation may underlie the proposed roles of the cytochromes in dampening inflammatory responses and the reported associations of certain CYP4F2 and CYP4F3
3158:
Watzer B, Reinalter S, Seyberth HW, Schweer H (2000). "Determination of free and glucuronide conjugated 20-hydroxyarachidonic acid (20-HETE) in urine by gas chromatography/negative ion chemical ionization mass spectrometry".
1104:
exhibit elevated levels of CYP4A2 and 20-HETE; blockade of 20-HETE production lowers blood pressure in this model. The effect is particularly well seen in female rats: aging post-menopausal but not pre-menopausal female
3235:
Hill E, Murphy RC (May 1992). "Quantitation of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) produced by human polymorphonuclear leukocytes using electron capture ionization gas chromatography/mass spectrometry".
1857:"CYP4 enzymes as potential drug targets: Focus on enzyme multiplicity, inducers and inhibitors, and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid Ο-hydroxylase activities"
7524:
6660:
6395:
2663:
Kikuta Y, Kusunose E, Sumimoto H, Mizukami Y, Takeshige K, Sakaki T, et al. (1998). "Purification and characterization of recombinant human neutrophil leukotriene B4 omega-hydroxylase (cytochrome P450 4F3)".
1306:
The incidence of cerebral and myocardial infarction in these studies appears to be independent of hypertension. (The platelets of individuals heterozygous or homozygous for the Val433Met variant exhibit increased
509:)-HETE, inhibits the action of 20-HETE on vascular endothelial cells. Based on studies analyzing the production of other HETEs by CYP enzymes, the production of 19-HETE by these enzymes may include both its
3347:
Zhang F, Wang MH, Wang JS, Zand B, Gopal VR, Falck JR, et al. (2004). "Transfection of CYP4A1 cDNA decreases diameter and increases responsiveness of gracilis muscle arterioles to constrictor stimuli".
1055:
which in turn stimulates the adhesion of platelets to the endothelial cells. The endothelial, platelet, and pro-clotting actions of 20-HETE may contribute to its ability to disrupt blood flood to tissues.
2101:
Toselli F, Booth Depaz IM, Worrall S, Etheridge N, Dodd PR, Wilce PA, et al. (2015). "Expression of CYP2E1 and CYP2U1 proteins in amygdala and prefrontal cortex: Influence of alcoholism and smoking".
5141:
Citterio A, Arnoldi A, Panzeri E, d'Angelo MG, Filosto M, Dilena R, et al. (2014). "Mutations in CYP2U1, DDHD2 and GBA2 genes are rare causes of complicated forms of hereditary spastic paraparesis".
2989:"Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products"
5721:
Guo M, Roman RJ, Falck JR, Edwards PA, Scicli AG (2005). "Human U251 glioma cell proliferation is suppressed by HET0016 N-hydroxy-N'-(4-butyl-2-methylphenyl)formamidine, a selective inhibitor of CYP4A".
1325:
of CYP4F2 is associated with essential hypertension in men only in a study of 249 hypertensive versus 238 age-matched controls in Japan. The impact of this variant on CYP4F2 expression is not known.
5817:
5678:
Rieger MA, Ebner R, Bell DR, Kiessling A, Rohayem J, Schmitz M, et al. (2004). "Identification of a novel mammary-restricted cytochrome P450, CYP4Z1, with overexpression in breast carcinoma".
1285:
among a large number of
Swedish patients enrolled and monitored over 10 years in the cardiovascular cohort of the MalmΓΆ Diet and Cancer Study only males with this variant exhibited hypertension;
4866:
1413:
Messenger RNAs not only for CYP4Z2 but also for CYP4A11, CYP4A22, CYP4F2, and CYP4F3 are more highly expressed in samples of human breast cancer tumors compared to normal breast tissue. The
1352:
as well as other cytochrome P450 proteins; the p.Asp314Val mutation is located in the enzyme's functional domain, is predicted to be damaging to the enzyme's activity, and is associated with
3271:
Tsai IJ, Croft KD, Puddey IB, Beilin LJ, Barden A (Apr 2011). "20-Hydroxyeicosatetraenoic acid synthesis is increased in human neutrophils and platelets by angiotensin II and endothelin-1".
5635:
Downie D, McFadyen MC, Rooney PH, Cruickshank ME, Parkin DE, Miller ID, et al. (2005). "Profiling cytochrome P450 expression in ovarian cancer: Identification of prognostic markers".
2066:
Devos A, Lino
Cardenas CL, Glowacki F, Engels A, Lo-Guidice JM, Chevalier D, et al. (2010). "Genetic polymorphism of CYP2U1, a cytochrome P450 involved in fatty acids hydroxylation".
1121:) and ameliorated by low salt intake. In this model, rats exhibit an up-regulated CYP4A/20-HETE pathway within their cerebral vasculature and vascular endothelial cell overproduction of
565:
Mouse CYP2J9, rat CYP2J3, and sheep CYP2J metabolize arachidonic acid primarily to 19-HETE but also to smaller amounts of 20-HETE, and, in the case of the sheep enzyme, 18-HETE; human
4739:
Munshi A, Sharma V, Kaul S, Al-Hazzani A, Alshatwi AA, Shafi G, et al. (2012). "Association of 1347 G/A cytochrome P450 4F2 (CYP4F2) gene variant with hypertension and stroke".
913:
In various rodent models, 20-HETE, at low concentrations (<50 nanomolar), acts to constrict arteries by sensitizing (i.e. increasing) the contraction responses of these artery's
7285:
1467:
increased ability to metabolize arachidonic acid to 20-HETE. Ovarian cancers also overexpress CYP4Z1 mRNA protein; this overexpression is associated with a poorer disease outcome.
3115:
Ward NC, Rivera J, Hodgson J, Puddey IB, Beilin LJ, Falck JR, et al. (2004). "Urinary 20-hydroxyeicosatetraenoic acid is associated with endothelial dysfunction in humans".
1314:. This platelet hyper-responsiveness to epinephrine, particularly if also exhibited to other platelet-aggregating agents, could contribute to cerebral and coronary infarctions.)
3383:
Kaide J, Zhang F, Wei Y, Wang W, Gopal VR, Falck JR, et al. (2004). "Vascular CO counterbalances the sensitizing influence of 20-HETE on agonist-induced vasoconstriction".
1170:; these effects are presumed but not yet shown to be due to the overproduction of 20-HETE. The Cyp4a12-transgenic model (above) is referred to in support of this presumption.
1747:
Bylund J, Ericsson J, Oliw EH (1998). "Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS".
664:
The cytochrome Ο-oxidases including those belonging to the CYP4A and CYP4F sub-families and CYPU21 hydroxylate not only arachidonic acid but also various shorter chain (e.g.
6049:
5810:
4247:
Imaoka S, Ogawa H, Kimura S, Gonzalez FJ (1993). "Complete cDNA sequence and cDNA-directed expression of CYP4A11, a fatty acid omega-hydroxylase expressed in human kidney".
1518:
exhibited significantly elevated levels of plasma and urinary 20-HETE compared to matched controls; women with the syndrome had particularly higher urinary 20-HETE levels.
1146:
Androgen treatment causes hypertension in normal male and female rats; this hypertensive response is greatly reduced by diverse inhibitors of Cyp4a and 20-HETE production.
1348:
in that it segregates with the disease at the homozygous state in two afflicted families. The mutation affects an amino acid (p.Asp316Val) highly conserved among CYP2U1
5765:
Tsai IJ, Croft KD, Mori TA, Falck JR, Beilin LJ, Puddey IB, et al. (2009). "20-HETE and F2-isoprostanes in the metabolic syndrome: The effect of weight reduction".
5098:
Wortmann SB, Espeel M, Almeida L, Reimer A, Bosboom D, Roels F, et al. (2015). "Inborn errors of metabolism in the biosynthesis and remodelling of phospholipids".
4402:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008). "A haplotype of the CYP4A11 gene associated with essential hypertension in
Japanese men".
4931:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2009). "A haplotype of the CYP4F2 gene associated with myocardial infarction in
Japanese men".
436:. Preclinical studies also suggest that the overproduction of 20-HETE may contribute to the progression of certain human cancers, particularly those of the breast.
5803:
1394:
mice show a greater increase in tumor weight and vascularity compared to control T47D cells; these increases are prevented by an inhibitor of 20-HETE production.
1281:
among 161 hypertensive and 74 normotensive subjects in
Australia, the incidence of the Val433Met variant was significantly increased in the hypertensive subjects;
1963:
Corcos L, Lucas D, Le Jossic-Corcos C, DrΓ©ano Y, Simon B, PlΓ©e-Gautier E, et al. (2012). "Human cytochrome P450 4F3: Structure, functions, and prospects".
3428:"Dietary Omega-3 Polyunsaturated Fatty Acids Prevent Vascular Dysfunction and Attenuate Cytochrome P4501A1 Expression by 2,3,7,8-Tetrachlorodibenzo-P-Dioxin"
895:
and platelets and by the ascending tubule cells in the medulla as well the pre-glomerular arterioles and certain other localized areas of the rabbit kidney.
114:
5407:
Zheng L, Li X, Gu Y, Lv X, Xi T (2015). "The 3'UTR of the pseudogene CYP4Z2P promotes tumor angiogenesis in breast cancer by acting as a ceRNA for CYP4Z1".
7003:
6288:
6022:
3076:"Metabolism of 20-hydroxyeicosatetraenoic acid by cyclooxygenase. Formation and identification of novel endothelium-dependent vasoconstrictor metabolites"
7231:
2546:"Renal drug metabolism in humans: The potential for drug-endobiotic interactions involving cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT)"
299:
InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10-
1198:, also known as the capsaicin receptor and the vanilloid receptor 1), and through this receptor, cultured dorsal root ganglion cells taken from mice.
4828:"The effect of a single nucleotide polymorphism of the CYP4F2 gene on blood pressure and 20-hydroxyeicosatetraenoic acid excretion after weight loss"
4827:
5347:"Gene expression profiling reveals new aspects of PIK3CA mutation in ERalpha-positive breast cancer: Major implication of the Wnt signaling pathway"
5288:"HET0016, a selective inhibitor of 20-HETE synthesis, decreases pro-angiogenic factors and inhibits growth of triple negative breast cancer in mice"
4616:"Hypertension, cardiovascular risk and polymorphisms in genes controlling the cytochrome P450 pathway of arachidonic acid: A sex-specific relation?"
888:
large blood vessels. However, both the smooth muscle and endothelial cells obtained from mouse brain microvasculature, produce 20-HETE in culture.
3632:
Wang J, Li H, He J, Li B, Bao Q, Zhang X, et al. (2015). "20-Hydroxyeicosatetraenoic acid involved in endothelial activation and thrombosis".
3585:"20-Hydroxyeicosatetraenoic acid inhibition attenuates balloon injury-induced neointima formation and vascular remodeling in rat carotid arteries"
6527:
2899:"Omega-oxidation of 20-hydroxyeicosatetraenoic acid (20-HETE) in cerebral microvascular smooth muscle and endothelium by alcohol dehydrogenase 4"
979:; the blood vessels to which these dysfunctional endothelial cells belong are less able to dilate in response to the vasodilator, acetylcholine.
6532:
537:, which is expressed in a limited range of tissues such as human breast and ovary, may also metabolize arachidonic acid to 20-HETE while human
1712:, Narsimhaswamy D, Pritchard Jr KA, et al. (2008). "20-hydroxyeicosatetraenoic acid causes endothelial dysfunction via eNOS uncoupling".
1109:
exhibit highly significant falls in blood pressure when treated with non-selective or selective inhibitors of CYP-induced 20-HETE production.
7614:
7474:
6486:
6415:
2742:"Interactions between the dietary polyunsaturated fatty acid ratio and genetic factors determine susceptibility to pediatric Crohn's disease"
6665:
312:
7469:
7330:
6725:
6624:
6577:
6507:
4104:
Fidelis P, Wilson L, Thomas K, Villalobos M, Oyekan AO (2010). "Renal function and vasomotor activity in mice lacking the Cyp4a14 gene".
7574:
3308:"Structural identification of cytochrome P450-dependent arachidonate metabolites formed by rabbit medullary thick ascending limb cells"
3035:"A single nucleotide polymorphism in the CYP4F2 but not CYP4A11 gene is associated with increased 20-HETE excretion and blood pressure"
3718:"Roles played by 20-HETE, angiotensin II and endothelin in mediating the hypertension in aging female spontaneously hypertensive rats"
1336:(2024C>G P85A; 80 C>T A27V rs771576634; 139C>T R47C rs115517770) which may affect conversion of arachidonic acid to HETE-20.
830:
Cultured smooth muscle and endothelial cells from mouse brain microvasculature oxidize 20-HETE to its 20-carboxy analog, 20-carboxy- 5
7589:
5496:"Cytochrome P450 Ο-hydroxylase promotes angiogenesis and metastasis by upregulation of VEGF and MMP-9 in non-small cell lung cancer"
3814:
Crofton JT, Ota M, Share L (1993). "Role of vasopressin, the renin-angiotensin system and sex in Dahl salt-sensitive hypertension".
213:
6567:
1375:
6806:
6778:
1460:
6445:
2140:
Murray GI, Patimalla S, Stewart KN, Miller ID, Heys SD (2010). "Profiling the expression of cytochrome P450 in breast cancer".
1628:"CYP2U1, a novel human thymus- and brain-specific cytochrome P450, catalyzes omega- and (omega-1)-hydroxylation of fatty acids"
1044:
632:
4651:
6832:
6798:
3536:"Impact of vascular thromboxane prostanoid receptor activation on hemostasis, thrombosis, oxidative stress, and inflammation"
2940:"Downregulation of human platelet reactivity by neutrophils. Participation of lipoxygenase derivatives and adhesive proteins"
1040:
176:
4198:"20-Hydroxyeicosatetraenoic acid (20-HETE) is a novel activator of transient receptor potential vanilloid 1 (TRPV1) channel"
1463:
cell lines in culture; the 20-HETE antagonist also inhibited the growth of 786-O cells transplanted into athymic nude mice.
945:. likewise stimulate 20-HETE production and have vasoconstrictive actions which are enhanced by 20-HETE. These circular or
5826:
1383:
7569:
6685:
6425:
1670:
Hardwick JP (2008). "Cytochrome P450 omega hydroxylase (CYP4) function in fatty acid metabolism and metabolic diseases".
1455:
cells. A selective inhibitor of 20-HETE synthesis and a 20-HETE antagonist reduced the growth of two human kidney cancer
1256:) variant of CYP4A11, C296T (cytosine to thymine at position 296), was associated with a significantly increased risk of
953:
5051:"Alteration of fatty-acid-metabolizing enzymes affects mitochondrial form and function in hereditary spastic paraplegia"
4488:"A polymorphism regulates CYP4A11 transcriptional activity and is associated with hypertension in a Japanese population"
2794:"Determination of major UDP-glucuronosyltransferase enzymes and their genotypes responsible for 20-HETE glucuronidation"
1357:
thereby 20-HETE's activation of the TRPV1 receptor in nerve tissues, it is hypothesized, may contribute to the disease.
4677:"The V433M variant of the CYP4F2 is associated with ischemic stroke in male Swedes beyond its effect on blood pressure"
4579:
Stec DE, Roman RJ, Flasch A, Rieder MJ (2007). "Functional polymorphism in human CYP4F2 decreases 20-HETE production".
4447:"Association of the T8590C polymorphism of CYP4A11 with hypertension in the MONICA Augsburg echocardiographic substudy"
1068:
in the epithelial cells of the proximal tubules of the kidney; the kinase then phosphorylates and thereby inhibits the
5545:"Down-regulation of 20-HETE synthesis and signaling inhibits renal adenocarcinoma cell proliferation and tumor growth"
458:
283:
2628:
Konkel A, Schunck WH (2011). "Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids".
541:, once considered as contributing to 20-HETE production, is now regarded as being metabolically inactive. Finally,
1167:
672:) fatty acids. They can also Ο-hydroxylate and thereby reduce the activity of various fatty acid metabolites (e.g.
4284:"Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension"
2593:
Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".
2236:"Arachidonic acid monooxygenase: Genetic and biochemical approaches to physiological/pathophysiological relevance"
1539:
Kroetz DL, Xu F (2005). "Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation".
384:
7647:
1414:
1117:
Dahl salt-sensitive rats develop hypertension that develops more quickly and exacerbated by high intake of salt (
1077:
4149:"Salt-sensitive hypertension is associated with dysfunctional Cyp4a10 gene and kidney epithelial sodium channel"
3859:"Testosterone-dependent hypertension and upregulation of intrarenal angiotensinogen in Dahl salt-sensitive rats"
7534:
6955:
6950:
6400:
1329:
1318:
1274:
1249:
1106:
1101:
2771:
6935:
6930:
5877:
4787:"Haplotype-based case-control study of the human CYP4F2 gene and essential hypertension in Japanese subjects"
1345:
930:
433:
7643:
6920:
6481:
4057:"Increased renal proximal convoluted tubule transport contributes to hypertension in Cyp4a14 knockout mice"
3482:"Isolated human and rat cerebral arteries constrict to increases in flow: role of 20-HETE and TP receptors"
963:
Studies in rats also indicate that in vascular endothelial cells 20-HETE inhibits the association of the
720:
681:
628:
247:
1194:
20-HETE activates the mouse and human transient receptor potential cation channel subfamily V member 1 (
25:
1452:
1426:
999:
723:(UGTs) is thought to be a primary pathway of 20-HETE elimination and thereby inactivation in humans.
697:
559:
264:
4693:
4300:
7035:
6945:
6940:
6925:
6742:
6242:
5872:
5867:
1390:-2. T47D cells that overexpress CYP4Z1 also overproduce 20-HETE and when transplanted into athymic
1179:
1039:-inducing agent, ferric chloride, in the common carotid and femoral arteries; companion studies on
926:
207:
627:
binding site of the 20-HETE producing cytochrome p450 enzymes. Drugs that are substrates for the
7226:
7008:
5586:"Targeting 20-HETE producing enzymes in cancer - rationale, pharmacology, and clinical potential"
5286:
Borin TF, Zuccari DA, Jardim-Perassi BV, Ferreira LC, Iskander AS, Varma NR, et al. (2014).
1122:
862:-octadecatetraenoic acid, and then to the further chain-shortened dicarboxylic acid, 16-carboxy-5
4532:"Association of common variants of CYP4A11 and CYP4F2 with stroke in the Han Chinese population"
589:
are particularly potent stimulators of this production. Other stimulators include the powerful
7529:
7376:
7093:
6965:
6871:
6237:
5882:
4688:
4295:
3949:"Androgen-sensitive hypertension associates with upregulated vascular CYP4A12-20-HETE synthase"
3857:
Yanes LL, Sartori-Valinotti JC, Iliescu R, Romero DG, Racusen LC, Zhang H, et al. (2009).
1230:
1048:
957:
4388:
3998:"Alterations in the regulation of androgen-sensitive Cyp 4a monooxygenases cause hypertension"
2606:
2011:"Increased expression of CYP4Z1 promotes tumor angiogenesis and growth in human breast cancer"
1552:
7667:
7204:
5345:
Cizkova M, Cizeron-Clairac G, Vacher S, Susini A, Andrieu C, Lidereau R, et al. (2010).
4376:
2845:"Biological activity and metabolism of 20-hydroxyeicosatetraenoic acid in the human platelet"
1302:
1073:
1052:
982:
20-HETE can also constrict rodent (and human) artery preparations by directly activating the
972:
968:
154:
3908:"Inhibition of renal outer medullary 20-HETE production produces hypertension in Lewis rats"
1344:
A mutation (c.947A>T) in CYP2U1 has been associated with a small number of patients with
7677:
7672:
7584:
7405:
7347:
7276:
7184:
7137:
6572:
6435:
6373:
6353:
6227:
5915:
5358:
5299:
5252:
5205:
4009:
2393:"Androgen-induced hypertension in angiotensinogen deficient mice: Role of 20-HETE and EETS"
2193:
2022:
1499:
1486:
1307:
1289:
among several hundred subjects in India, the variant was associated with hypertension; and
983:
669:
90:
38:
4826:
Ward NC, Croft KD, Puddey IB, Phillips M, Van
Bockxmeer F, Beilin LJ, et al. (2014).
3767:"Role of the CYP4A/20-HETE pathway in vascular dysfunction of the Dahl salt-sensitive rat"
268:
8:
7489:
7409:
7351:
7309:
7251:
7019:
6198:
4631:
4333:
Gainer JV, Lipkowitz MS, Yu C, Waterman MR, Dawson EP, Capdevila JH, et al. (2008).
3033:
Ward NC, Tsai IJ, Barden A, Van
Bockxmeer FM, Puddey IB, Hodgson JM, et al. (2008).
2404:
2356:
2251:
1812:
1298:
914:
80:
5778:
5362:
5303:
5256:
5209:
4013:
3194:
Kaduce TL, Fang X, Harmon SD, Oltman CL, Dellsperger KC, Teesch LM, et al. (2004).
2197:
2026:
134:
7370:
7236:
7031:
6977:
6542:
6216:
6108:
5894:
5841:
5747:
5703:
5660:
5612:
5585:
5561:
5544:
5520:
5495:
5471:
5454:
5432:
5381:
5346:
5322:
5287:
5177:
5123:
5075:
5050:
4992:
4892:"A haplotype of the CYP4F2 gene is associated with cerebral infarction in Japanese men"
4858:
4764:
4716:
4703:
4676:
4643:
4592:
4556:
4531:
4504:
4487:
4463:
4446:
4427:
4359:
4334:
4310:
4283:
4224:
4197:
4173:
4148:
4129:
4081:
4056:
3973:
3948:
3883:
3858:
3839:
3791:
3766:
3742:
3717:
3693:
3668:
3609:
3584:
3565:
3506:
3481:
3452:
3427:
3408:
3396:
3140:
3128:
3051:
3034:
2869:
2860:
2844:
2820:
2793:
2570:
2545:
2521:
2496:
2472:
2413:
2392:
2365:
2340:
2309:
2284:
2260:
2235:
2165:
2043:
2010:
1988:
1937:
1912:
1881:
1856:
1821:
1796:
1600:
1575:
1515:
1435:
701:
4486:
Sugimoto K, Akasaka H, Katsuya T, Node K, Fujisawa T, Shimaoka I, et al. (2008).
3324:
3307:
3092:
3075:
2964:
2939:
558:
distribution of these enzymes differs from those of humans making extrapolations from
470:
in most tissues for forming 20-HETE and, concurrently, smaller amounts of 19-hydroxy-5
7564:
7087:
6675:
6598:
6589:
6420:
6189:
6144:
6134:
6079:
6032:
5832:
5782:
5739:
5695:
5652:
5617:
5566:
5525:
5476:
5424:
5386:
5327:
5268:
5221:
5169:
5115:
5080:
5028:
4984:
4948:
4913:
4850:
4808:
4756:
4708:
4635:
4596:
4561:
4509:
4468:
4419:
4364:
4315:
4264:
4229:
4178:
4121:
4086:
4037:
4032:
3997:
3978:
3929:
3888:
3831:
3827:
3796:
3747:
3698:
3649:
3614:
3557:
3511:
3457:
3400:
3365:
3329:
3288:
3253:
3217:
3176:
3132:
3097:
3056:
3010:
2969:
2938:
Valles J, Santos MT, Marcus AJ, Safier LB, Broekman MJ, Islam N, et al. (1993).
2920:
2874:
2825:
2763:
2722:
2681:
2645:
2610:
2575:
2526:
2464:
2418:
2370:
2314:
2265:
2209:
2157:
2153:
2119:
2083:
2048:
1980:
1942:
1886:
1826:
1764:
1729:
1687:
1649:
1605:
1556:
1395:
1387:
1225:
946:
623:
inhibit 20-HETE production; these non-pharmacological agents do so by binding to the
5751:
5664:
5436:
5181:
5127:
5049:
Tesson C, Nawara M, Salih MA, Rossignol R, Zaki MS, Al Balwi M, et al. (2012).
4996:
4768:
4675:
Fava C, Montagnana M, Almgren P, Rosberg L, Lippi G, Hedblad B, et al. (2008).
4431:
4282:
Gainer JV, Bellamine A, Dawson EP, Womble KE, Grant SW, Wang Y, et al. (2005).
4196:
Wen H, Γstman J, Bubb KJ, Panayiotou C, Priestley JV, Baker MD, et al. (2012).
3843:
3569:
3196:"20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells"
956:
to promote the entry of ionic calcium into vascular smooth muscle cells through the
235:
7499:
7265:
7103:
6512:
6173:
5857:
5774:
5731:
5707:
5687:
5644:
5607:
5597:
5556:
5515:
5507:
5466:
5416:
5376:
5366:
5317:
5307:
5260:
5213:
5159:
5151:
5107:
5070:
5062:
5020:
4976:
4940:
4903:
4862:
4842:
4798:
4748:
4720:
4698:
4647:
4627:
4588:
4551:
4543:
4499:
4458:
4411:
4354:
4346:
4305:
4256:
4219:
4209:
4168:
4160:
4113:
4076:
4068:
4027:
4017:
3968:
3960:
3919:
3878:
3870:
3823:
3786:
3778:
3737:
3729:
3688:
3680:
3641:
3604:
3596:
3547:
3501:
3493:
3447:
3439:
3392:
3357:
3319:
3280:
3245:
3207:
3168:
3144:
3124:
3087:
3046:
3000:
2959:
2951:
2910:
2864:
2856:
2815:
2805:
2753:
2712:
2673:
2637:
2602:
2565:
2557:
2516:
2508:
2476:
2454:
2408:
2400:
2360:
2352:
2304:
2296:
2255:
2247:
2201:
2169:
2149:
2111:
2075:
2038:
2030:
1992:
1972:
1932:
1924:
1876:
1868:
1816:
1808:
1756:
1721:
1679:
1639:
1595:
1587:
1548:
1430:
1065:
976:
938:
882:
735:
602:
590:
462:
420:
335:
5691:
5648:
4133:
3412:
2897:
Collins XH, Harmon SD, Kaduce TL, Berst KB, Fang X, Moore SA, et al. (2005).
960:; the attendant rise in intracellular calcium triggers these muscles to contract.
585:
Many agents stimulate cells and tissues to produce 20-HETE in vitro and in vivo.
7619:
7539:
7342:
7335:
6737:
6730:
6670:
6582:
6450:
6405:
5952:
5862:
5371:
5312:
4980:
4846:
4547:
4415:
2758:
2740:
Costea I, Mack DR, Lemaitre RN, Israel D, Marcil V, Ahmad A, et al. (2014).
2641:
2512:
2283:
Messina A, Nencioni S, Gervasi PG, Gotlinger KH, Schwartzman ML, Longo V (2010).
1928:
1872:
1626:
Chuang SS, Helvig C, Taimi M, Ramshaw HA, Collop AH, Amad M, et al. (2004).
1257:
1118:
1069:
783:
716:
705:
616:
466:
450:
424:
5024:
4944:
4445:
Mayer B, Lieb W, GΓΆtz A, KΓΆnig IR, Aherrahrou Z, Thiemig A, et al. (2005).
3874:
3645:
3361:
3284:
2079:
1725:
7366:
7281:
7051:
6973:
6680:
6212:
6119:
6089:
5982:
5890:
5264:
5217:
5066:
3733:
3684:
2391:
Garcia V, Cheng J, Weidenhammer A, Ding Y, Wu CC, Zhang F, et al. (2015).
2034:
1503:
1434:
promoting its survival, growth, and vascular endothelial growth factor-induced
1261:
1134:
1010:
987:
942:
875:
743:
739:
731:
689:
606:
594:
494:
can metabolize arachidonic acid to 19-HETE while forming little or no 20-HETE.
378:
68:
20-HETE, 20-Hydroxy-5,8,11,14-eicosatetraenoic, 20-Hydroxyeicosatetraenoic acid
5511:
5420:
5155:
5111:
4752:
2300:
2205:
1683:
1591:
7661:
7599:
7579:
7174:
6889:
6720:
6700:
6430:
6318:
6129:
6002:
5919:
4890:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).
4785:
Fu Z, Nakayama T, Sato N, Izumi Y, Kasamaki Y, Shindo A, et al. (2008).
3947:
Wu CC, Mei S, Cheng J, Ding Y, Weidenhammer A, Garcia V, et al. (2013).
3667:
Yanes LL, Lima R, Moulana M, Romero DG, Yuan K, Ryan MJ, et al. (2011).
3583:
Orozco LD, Liu H, Perkins E, Johnson DA, Chen BB, Fan F, et al. (2013).
1709:
1218:
1163:
5735:
4260:
4214:
4117:
3996:
Holla VR, Adas F, Imig JD, Zhao X, Price Jr E, Olsen N, et al. (2001).
3924:
3907:
3600:
3443:
3005:
2988:
2717:
2700:
1031:
mouse laboratory model, 20-HETE pretreatment accelerates the development of
7479:
7295:
7255:
7188:
7178:
7169:
7164:
7107:
7065:
6655:
6440:
6349:
6262:
6074:
6069:
5972:
5786:
5743:
5699:
5656:
5621:
5570:
5529:
5480:
5428:
5390:
5331:
5272:
5225:
5173:
5119:
5084:
5032:
4988:
4952:
4917:
4854:
4812:
4803:
4786:
4760:
4712:
4639:
4600:
4565:
4513:
4472:
4423:
4368:
4350:
4319:
4233:
4182:
4147:
Nakagawa K, Holla VR, Wei Y, Wang WH, Gatica A, Wei S, et al. (2006).
4125:
4090:
4041:
4022:
3982:
3964:
3892:
3800:
3751:
3702:
3653:
3618:
3561:
3515:
3461:
3404:
3369:
3292:
3249:
3221:
3212:
3195:
3180:
3172:
3136:
3060:
3014:
2924:
2915:
2898:
2829:
2767:
2726:
2677:
2649:
2614:
2579:
2530:
2468:
2422:
2374:
2318:
2269:
2213:
2161:
2123:
2087:
2052:
1984:
1976:
1946:
1890:
1830:
1760:
1733:
1691:
1653:
1644:
1627:
1609:
1560:
1379:
1353:
1175:
995:
964:
693:
612:
502:
5543:
Alexanian A, Rufanova VA, Miller B, Flasch A, Roman RJ, Sorokin A (2009).
4268:
3933:
3835:
3497:
3333:
3257:
3101:
2973:
2878:
2685:
1768:
7519:
7447:
7431:
7299:
7271:
7154:
7098:
7041:
7027:
6715:
6710:
6650:
6379:
6364:
6359:
6313:
6252:
6179:
6159:
6138:
6099:
5962:
5927:
5795:
4908:
4891:
2386:
2384:
2334:
2332:
2330:
2328:
1311:
1127:
918:
892:
806:-eicosatetraenoic acid which is also rapidly reduced to 12,20-dihydroxy-5
665:
640:
570:
549:
human breast cancer cell line express messenger RNA for this cytochrome.
2810:
2792:
Jarrar YB, Cha EY, Seo KA, Ghim JL, Kim HJ, Kim DH, et al. (2014).
2459:
2442:
1498:
20-HETE constricts human artery preparations by directly activating the
1297:
The Val433Met variant is also associated with an increased incidence of
1080:(TALH); these effects reduce the absorption of sodium and fluids in the
7509:
7400:
7315:
7305:
7261:
7245:
7241:
7132:
6998:
6866:
6849:
6747:
6593:
6521:
6517:
6464:
6410:
6369:
6194:
6184:
6169:
6037:
5947:
5602:
5164:
3782:
2115:
1418:
1399:
1234:
1155:
1036:
1032:
922:
620:
598:
416:
363:
166:
145:
6903:
6761:
6332:
4615:
4072:
3552:
3535:
2955:
2561:
2443:"Role of 20-hydroxyeicosatetraenoic acid (20-HETE) in vascular system"
2381:
2325:
1576:"Cytochrome P450-derived eicosanoids: the neglected pathway in cancer"
7624:
7609:
7604:
7554:
7549:
7194:
7113:
7071:
7061:
6298:
6163:
4965:
4164:
2447:
Journal of Smooth Muscle
Research = Nihon Heikatsukin Gakkai Kikanshi
1407:
1349:
1245:
934:
823:
727:
586:
454:
5840:
1795:
Hoopes SL, Garcia V, Edin ML, Schwartzman ML, Zeldin DC (Jul 2015).
766:-eicosatetraenoic acid which is rapidly reduced to 11,20-dihydroxy-5
533:
mostly expressed in leukocytes, CYP4F3B mostly in the liver. Human
377:
Except where otherwise noted, data are given for materials in their
7559:
7544:
7513:
7503:
7493:
7483:
7464:
7452:
7421:
7416:
7380:
7291:
7144:
7083:
7055:
7045:
7023:
6705:
6690:
6614:
6552:
6537:
6497:
6303:
6278:
6231:
6222:
6149:
6115:
6059:
6054:
6016:
6012:
5986:
5976:
5966:
5956:
5942:
5900:
5494:
Yu W, Chen L, Yang YQ, Falck JR, Guo AM, Li Y, et al. (2011).
3856:
3534:
Capra V, BΓ€ck M, Angiolillo DJ, Cattaneo M, Sakariassen KS (2014).
2741:
1386:
while under expressing message and protein for tissue inhibitor of
648:
497:
The production of 19-HETE with 20-HETE may be significant since 19(
196:
5344:
5285:
5140:
4335:"Association of a CYP4A11 variant and blood pressure in black men"
3426:
Wiest EF, Walsh-Wilcox MT, Rothe M, Schunck WH, Walker MK (2016).
2100:
1183:
113:
7594:
7459:
7425:
7394:
7358:
7216:
7198:
7118:
7075:
7015:
6983:
6793:
6694:
6645:
6618:
6610:
6557:
6491:
6307:
6283:
6204:
6153:
6042:
5905:
3073:
2699:
Curley CR, Monsuur AJ, Wapenaar MC, Rioux JD, Wijmenga C (2006).
2285:"Molecular cloning and enzymatic characterization of sheep CYP2J"
1962:
1253:
1081:
1028:
726:
There are several other pathways that metabolize 20-HETE. Human
685:
636:
574:
538:
521:
222:
4055:
Quigley R, Chakravarty S, Zhao X, Imig JD, Capdevila JH (2009).
3634:
American
Journal of Physiology. Heart and Circulatory Physiology
3273:
American Journal of Physiology. Heart and Circulatory Physiology
2065:
2009:
Yu W, Chai H, Li Y, Zhao H, Xie X, Zheng H, et al. (2012).
1149:
949:
interactions may serve to perpetuate vasoconstrictor responses.
883:
Tissue distribution of 20-HETE-producing enzymes and/or activity
7386:
7362:
7320:
7220:
7148:
6987:
6969:
6827:
6788:
6783:
6561:
6547:
6292:
6208:
6103:
6094:
6084:
6063:
6026:
5997:
5992:
5931:
5923:
5909:
5886:
5634:
4530:
Ding H, Cui G, Zhang L, Xu Y, Bao X, Tu Y, et al. (2010).
2497:"Cytochrome P450 eicosanoids in hypertension and renal disease"
2282:
1447:
1391:
1322:
1015:
917:
to other contracting agents such as alpha adrenergic agonists,
677:
566:
542:
534:
529:
525:
491:
487:
429:
3157:
2662:
1913:"20-HETE and blood pressure regulation: Clinical implications"
1294:
increased arterial stiffness and increased 20-HETE synthesis.
7390:
7126:
7122:
7079:
6993:
6762:
6629:
6606:
6246:
6123:
6006:
5937:
5542:
5455:"20-HETE-producing enzymes are up-regulated in human cancers"
4103:
3425:
2630:
Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics
1573:
1456:
1446:
20-HETE stimulated the proliferation of cultured human brain
1422:
1403:
1195:
652:
644:
546:
490:
may also contribute to the production of these two HETEs and
125:
103:
4674:
2139:
998:
as well as to the physiological and pathological effects of
252:
7325:
7159:
6904:
6850:
6811:
6502:
6465:
6333:
5452:
5097:
4281:
3533:
3032:
2390:
1794:
1472:
1371:
673:
624:
187:
5048:
4738:
4485:
4054:
3306:
Carroll MA, Sala A, Dunn CE, McGiff JC, Murphy RC (1991).
3074:
Schwartzman ML, Falck JR, Yadagiri P, Escalante B (1989).
2698:
552:
4332:
4246:
2701:"A functional candidate screen for coeliac disease genes"
1911:
Wu CC, Gupta T, Garcia V, Ding Y, Schwartzman ML (2014).
1574:
Panigrahy D, Kaipainen A, Greene ER, Huang S (Dec 2010).
1264:
for large vessel disease stroke risk in this population.
5677:
3715:
2937:
2896:
2739:
1625:
782:-eicosatetraenoic acid; they also metabolize it through
580:
7210:
5013:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
4825:
4195:
3722:
AJP: Regulatory, Integrative and Comparative Physiology
3673:
AJP: Regulatory, Integrative and Comparative Physiology
3582:
3161:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
3114:
2341:"The role of 20-HETE in androgen-mediated hypertension"
2182:
2068:
Prostaglandins, Leukotrienes, and Essential Fatty Acids
1064:
In animal models, 20-HETE stimulates the activation of
4613:
3666:
3480:
Toth P, Rozsa B, Springo Z, Doczi T, Koller A (2011).
3193:
2986:
2135:
2133:
1398:, a proposed drug for treating cancer, cause cultured
1141:
5724:
Journal of Pharmacology and Experimental Therapeutics
4578:
3589:
Journal of Pharmacology and Experimental Therapeutics
3479:
3305:
3270:
2842:
1112:
5827:
5720:
4146:
2543:
5453:Alexanian A, Miller B, Roman RJ, Sorokin A (2012).
4930:
4889:
4784:
4401:
2892:
2890:
2888:
2130:
1096:
1043:indicate that 20-HETE stimulates the activation of
175:
5764:
4444:
3764:
3716:Lima R, Yanes LL, Davis DD, Reckelhoff JF (2013).
2233:
1746:
3995:
3382:
3346:
1910:
1707:
7659:
5583:
3905:
2885:
2791:
659:
234:
5493:
5448:
5446:
5402:
5400:
5241:
5237:
5235:
5194:
5044:
5042:
4780:
4778:
4734:
4732:
4730:
4670:
4668:
4525:
4523:
4002:Proceedings of the National Academy of Sciences
3813:
3529:
3527:
3525:
3475:
3473:
3471:
3028:
3026:
3024:
2490:
2488:
2486:
2436:
2434:
2432:
2229:
2227:
2225:
2223:
2004:
2002:
1958:
1956:
1406:human breast cancer cells to die by triggering
1221:in mice (see above section on genetic models).
1130:, the renin-angiotensin system, and androgens.
631:(UGT) enzymes which metabolize 20-HETE such as
214:acid 20-hydroxy-5,8,11,14-eicosatetraenoic acid
89:
4529:
3946:
3669:"Postmenopausal hypertension: Role of 20-HETE"
2501:Current Opinion in Nephrology and Hypertension
2494:
2104:Alcoholism: Clinical and Experimental Research
1906:
1904:
1902:
1900:
1850:
1848:
1846:
1844:
1842:
1840:
1703:
1701:
1665:
1663:
1621:
1619:
1382:overexpress messenger RNA for and overproduce
1178:-inducing and anti-hypertensive products, the
952:Again in rodent models, 20-HETE acts to block
898:
5811:
4614:Fava C, Ricci M, Melander O, Minuz P (2012).
4339:Journal of the American Society of Nephrology
3953:Journal of the American Society of Nephrology
3486:Journal of Cerebral Blood Flow and Metabolism
2627:
2338:
1790:
1788:
1786:
1784:
1782:
1780:
1778:
1567:
1534:
1532:
1530:
1150:Genetically engineered models of hypertension
5758:
5714:
5671:
5628:
5577:
5536:
5487:
5443:
5397:
5338:
5279:
5232:
5188:
5134:
5091:
5039:
5003:
4959:
4924:
4883:
4819:
4775:
4727:
4665:
4607:
4572:
4520:
4479:
4438:
4395:
4326:
4275:
4189:
4140:
4097:
4048:
3989:
3940:
3850:
3758:
3709:
3660:
3625:
3576:
3522:
3468:
3419:
3376:
3340:
3187:
3151:
3108:
3021:
2987:Thuresson ED, Lakkides KM, Smith WL (2000).
2980:
2785:
2733:
2692:
2621:
2595:Annual Review of Pharmacology and Toxicology
2586:
2537:
2483:
2429:
2276:
2220:
2176:
2094:
2059:
2008:
1999:
1953:
1541:Annual Review of Pharmacology and Toxicology
1471:production blocks the growth of human brain
1328:Researchers have identified at least 3 more
1321:rs1558139 guanine to cytosine variant in an
1241:genotype versus homozygous -845A was 1.42);
846:-eicosatetraenoic acid, then to 18-carboxy-5
486:-eicosatetraenoic acid (19-HETE). However,
5406:
5009:
4240:
3899:
3807:
3299:
3067:
2931:
2836:
2656:
2440:
1897:
1854:
1837:
1698:
1660:
1616:
1084:and thereby tend to reduce blood pressure.
908:
520:In humans, the CYP4 Ο-hydroxylases include
59:)-20-Hydroxyicosa-5,8,11,14-tetraenoic acid
5825:
5818:
5804:
4620:Prostaglandins & Other Lipid Mediators
3631:
3234:
2397:Prostaglandins & Other Lipid Mediators
2345:Prostaglandins & Other Lipid Mediators
2240:Prostaglandins & Other Lipid Mediators
1801:Prostaglandins & Other Lipid Mediators
1775:
1740:
1527:
1514:One study found that 30 patients with the
1022:
267:
153:
5611:
5601:
5560:
5519:
5470:
5380:
5370:
5321:
5311:
5163:
5074:
4907:
4802:
4702:
4692:
4555:
4503:
4462:
4358:
4309:
4299:
4223:
4213:
4172:
4080:
4031:
4021:
3972:
3923:
3882:
3790:
3741:
3692:
3608:
3551:
3505:
3451:
3323:
3228:
3211:
3091:
3050:
3004:
2963:
2914:
2868:
2843:Hill E, Fitzpatrick F, Murphy RC (1992).
2819:
2809:
2757:
2716:
2607:10.1146/annurev.pharmtox.45.120403.100045
2569:
2544:Knights KM, Rowland A, Miners JO (2013).
2520:
2458:
2412:
2364:
2308:
2259:
2042:
1936:
1880:
1820:
1643:
1599:
1553:10.1146/annurev.pharmtox.45.120403.100045
1217:the hypertension associated with Cyp4a14
2592:
2550:British Journal of Clinical Pharmacology
1669:
1538:
423:that has a wide range of effects on the
320:C(CC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)CCO
2666:Archives of Biochemistry and Biophysics
2234:Capdevila JH, Wang W, Falck JR (2015).
1479:
1211:
874:-hexadecatrrenoic acid, in a series of
553:Production by rodents and other animals
444:
399:, also known as 20-HETE or 20-hydroxy-5
263:
212:
7660:
5100:Journal of Inherited Metabolic Disease
5055:The American Journal of Human Genetics
3906:Stec DE, Mattson DL, Roman RJ (1997).
1267:
1045:Extracellular signal-regulated kinases
1041:human umbilical vein endothelial cells
1005:
734:(s) to form the 20-hydroxy analogs of
633:non-steroidal anti-inflammatory agents
5998:CS gas (2-chlorobenzal malononitrile)
5799:
3540:Journal of Thrombosis and Haemostasis
3350:AJP: Heart and Circulatory Physiology
1965:Drug Metabolism and Drug Interactions
1861:Current Topics in Medicinal Chemistry
1714:AJP: Heart and Circulatory Physiology
1509:
1035:and reduces blood flow caused by the
581:Factors regulating 20-HETE production
292:Key: NNDIXBJHNLFJJP-DTLRTWKJSA-N
133:
5500:Cancer Chemotherapy and Pharmacology
5409:Breast Cancer Research and Treatment
4969:Blood Coagulation & Fibrinolysis
4632:10.1016/j.prostaglandins.2011.11.007
2405:10.1016/j.prostaglandins.2014.12.001
2357:10.1016/j.prostaglandins.2011.06.006
2252:10.1016/j.prostaglandins.2015.05.004
1813:10.1016/j.prostaglandins.2015.03.002
1417:(3'UTRs) of the CYP4Z1 gene and its
1384:vascular endothelial growth factor A
1370:Two human breast cancer cell lines,
1233:in: 512 white males from Tennessee (
954:Calcium-activated potassium channels
730:and other tissues metabolize it via
7570:N-(p-Amylcinnamoyl)anthranilic acid
6686:N-(p-Amylcinnamoyl)anthranilic acid
6426:N-(p-Amylcinnamoyl)anthranilic acid
5779:10.1016/j.freeradbiomed.2008.10.028
5245:Toxicology and Applied Pharmacology
5198:Toxicology and Applied Pharmacology
3765:Lukaszewicz KM, Lombard JH (2013).
3312:The Journal of Biological Chemistry
3080:The Journal of Biological Chemistry
2993:The Journal of Biological Chemistry
2015:Toxicology and Applied Pharmacology
1339:
1189:
1142:Androgen-induced hypertensive model
1059:
573:, metabolizing arachidonic acid to
225:
195:
13:
4704:10.1161/HYPERTENSIONAHA.108.114199
4593:10.1152/physiolgenomics.00003.2007
4505:10.1161/HYPERTENSIONAHA.108.114082
4464:10.1161/01.HYP.0000182658.04299.15
4311:10.1161/01.CIR.0000151309.82473.59
3397:10.1161/01.HYP.0000135658.57547.bb
3129:10.1161/01.CIR.0000136808.72912.D9
3052:10.1161/HYPERTENSIONAHA.107.104463
2861:10.1111/j.1476-5381.1992.tb14327.x
2705:European Journal of Human Genetics
2495:Fan F, Muroya Y, Roman RJ (2015).
1206:
1113:Salt-sensitive hypertension models
1076:and 70 pS K+ channel in the thick
459:Cytochrome P450 omega hydroxylases
14:
7689:
5767:Free Radical Biology and Medicine
4933:Molecular Genetics and Metabolism
4153:Journal of Clinical Investigation
4106:Experimental Biology and Medicine
2944:Journal of Clinical Investigation
1476:are responsible for its actions.
1072:and concurrently also blocks the
903:
656:enzymes and benzene-based drugs.
5459:Cancer Genomics & Proteomics
4896:American Journal of Hypertension
4841:(7): 1495β502, discussion 1502.
3828:10.1097/00004872-199310000-00005
2154:10.1111/j.1365-2559.2010.03606.x
1441:
1415:Three prime untranslated regions
1378:, made to overexpress CYP4Z1 by
1365:
1201:
1097:Spontaneously hypertensive model
562:to humans somewhat complicated.
347:
24:
19:20-Hydroxyeicosatetraenoic acid
5584:Alexanian A, Sorokin A (2013).
4872:from the original on 2019-10-01
4654:from the original on 2024-03-08
4202:Journal of Biological Chemistry
3264:
3200:Journal of Biological Chemistry
2903:Journal of Biological Chemistry
2849:British Journal of Pharmacology
2774:from the original on 2020-07-03
2186:Chemico-Biological Interactions
1632:Journal of Biological Chemistry
1330:single-nucleotide polymorphisms
1107:spontaneously hypertensive rats
1102:Spontaneously hypertensive rats
1087:
1078:Ascending limb of loop of Henle
967:-producing enzyme, endothelial
439:
397:20-Hydroxyeicosatetraenoic acid
381:(at 25 Β°C , 100 kPa).
2339:Wu CC, Schwartzman ML (2011).
1493:
1319:Single-nucleotide polymorphism
1275:single-nucleotide polymorphism
1250:single-nucleotide polymorphism
822:-eicosatetraenoic acid. (The
415:-eicosatetraenoic acid, is an
353:
341:
1:
7644:Receptor/signaling modulators
5993:CR gas (dibenzoxazepine; DBO)
5692:10.1158/0008-5472.can-03-0849
5649:10.1158/1078-0432.CCR-05-0466
4536:Pharmacogenetics and Genomics
3325:10.1016/S0021-9258(18)98897-6
3093:10.1016/S0021-9258(18)80115-6
2798:The Journal of Lipid Research
1797:"Vascular actions of 20-HETE"
1580:Cancer and Metastasis Reviews
1521:
1346:Hereditary spastic paraplegia
931:angiotensin-converting enzyme
891:20-HETE is produced by human
711:
660:Proviso on 20-HETE production
434:Hereditary spastic paraplegia
5372:10.1371/journal.pone.0015647
5313:10.1371/journal.pone.0116247
4981:10.1097/MBC.0000000000000053
4847:10.1097/HJH.0000000000000208
4548:10.1097/FPC.0b013e328336eefe
4416:10.1097/HJH.0b013e3282f2f10c
3238:Biological Mass Spectrometry
2759:10.1053/j.gastro.2013.12.034
2642:10.1016/j.bbapap.2010.09.009
2513:10.1097/MNH.0000000000000088
1929:10.1097/CRD.0b013e3182961659
1873:10.2174/15680266113139990110
1855:Edson KZ, Rettie AE (2013).
1168:Sodiumβhydrogen antiporter 3
1162:Mice depleted of Cyp4a14 by
721:UDP-glucuronosyltransferases
668:) and/or longer chain (e.g.
7:
7272:Paracetamol (acetaminophen)
6180:Paracetamol (acetaminophen)
6050:Farnesyl thiosalicylic acid
5878:15-Deoxy-Ξ-prostaglandin J2
5025:10.1016/j.plefa.2018.02.003
4945:10.1016/j.ymgme.2008.11.161
3875:10.1152/ajprenal.90389.2008
3646:10.1152/ajpheart.00802.2014
3362:10.1152/ajpheart.00627.2003
3285:10.1152/ajpheart.00733.2010
2441:Miyata N, Roman RJ (2005).
2080:10.1016/j.plefa.2010.06.005
1726:10.1152/ajpheart.01172.2007
1047:to cause ERK-dependent and
899:Vascular-related activities
682:5-oxo-eicosatetraenoic acid
629:UDP-glucuronosyltransferase
457:-bound Ο-hydroxylases, the
10:
7694:
5265:10.1016/j.taap.2014.07.018
5218:10.1016/j.taap.2013.05.031
5067:10.1016/j.ajhg.2012.11.001
3734:10.1152/ajpregu.00380.2012
3685:10.1152/ajpregu.00387.2010
2035:10.1016/j.taap.2012.07.019
1453:non-small cell lung cancer
790:)-hydroperoxy-20-hydroxy-5
750:)-hydroperoxy-20-hydroxy-5
698:single nucleotide variants
7637:
7440:
6913:
6902:
6882:
6859:
6848:
6820:
6771:
6760:
6638:
6474:
6463:
6388:
6342:
6331:
6271:
5850:
5839:
5512:10.1007/s00280-010-1521-8
5421:10.1007/s10549-015-3298-2
5156:10.1007/s00415-013-7206-6
5112:10.1007/s10545-014-9759-7
4753:10.1007/s11033-011-0907-y
4741:Molecular Biology Reports
2301:10.3109/00498250903410590
2206:10.1016/j.cbi.2006.01.007
1708:Cheng J, Ou JS, Singh H,
1684:10.1016/j.bcp.2008.03.004
1592:10.1007/s10555-010-9264-x
1427:phosphoinositide 3-kinase
1421:, CYP4Z2P, share several
1360:
1180:Epoxyeicosatrienoic acids
501:)-HETE, although not its
375:
328:
308:
279:
73:
65:
37:
32:
23:
6257:Umbellularia californica
5637:Clinical Cancer Research
4622:(Submitted manuscript).
1672:Biochemical Pharmacology
933:. Other agents such as
927:renin angiotensin system
909:Blood vessel contraction
7227:N-Arachidonoyl dopamine
7009:Andrographis paniculata
5736:10.1124/jpet.105.088567
5590:OncoTargets and Therapy
4835:Journal of Hypertension
4404:Journal of Hypertension
4261:10.1089/dna.1993.12.893
4215:10.1074/jbc.M111.334896
4118:10.1258/ebm.2010.009233
3925:10.1161/01.HYP.29.1.315
3816:Journal of Hypertension
3601:10.1124/jpet.113.203844
3006:10.1074/jbc.275.12.8501
2718:10.1038/sj.ejhg.5201687
1749:Analytical Biochemistry
1123:reactive oxygen species
1023:Blood vessel thrombosis
7648:Ion channel modulators
7377:Tetrahydrocannabivarin
6872:Tripterygium wilfordii
6238:Tetrahydrocannabiorcol
4804:10.1291/hypres.31.1719
4581:Physiological Genomics
4351:10.1681/ASN.2008010063
4023:10.1073/pnas.081627898
3965:10.1681/ASN.2012070714
3432:Toxicological Sciences
3250:10.1002/bms.1200210505
3213:10.1074/jbc.M306849200
3173:10.1054/plef.2000.0138
2916:10.1074/jbc.M504055200
2678:10.1006/abbi.1998.0724
1977:10.1515/dmdi-2011-0037
1761:10.1006/abio.1998.2897
1645:10.1074/jbc.M311830200
1231:essential hypertension
1051:-dependent release of
1049:L-type calcium channel
958:L-type calcium channel
7205:Lysophosphatidic acid
4791:Hypertension Research
3863:AJP: Renal Physiology
3498:10.1038/jcbfm.2011.74
3444:10.1093/toxsci/kfw145
1303:myocardial infarction
1074:Na-K-Cl cotransporter
1053:von Willebrand factor
1014:reduced the vascular
973:heat shock protein 90
969:nitric oxide synthase
7585:Pregnenolone sulfate
7406:Euphorbia resinifera
7348:Euphorbia resinifera
7277:Phenylacetylrinvanil
7237:N-Oleoylethanolamide
7185:Homodihydrocapsaicin
6573:Pregnenolone sulfate
6436:Pregnenolone sulfate
6243:Thiopropanal S-oxide
6228:Tetrahydrocannabinol
5916:Allyl isothiocyanate
5144:Journal of Neurology
4909:10.1038/ajh.2008.276
4249:DNA and Cell Biology
1917:Cardiology in Review
1487:thromboxane receptor
1480:Platelet aggregation
1308:platelet aggregation
1212:CYP4A11 polymorphism
1000:thromboxane receptor
670:docosahexaenoic acid
445:Production in humans
39:Preferred IUPAC name
7490:Cannabigerolic acid
7252:Nordihydrocapsaicin
7213:(acidic conditions)
5549:Anticancer Research
5363:2010PLoSO...515647C
5304:2014PLoSO...9k6247B
5257:2014ToxAP.280...10Z
5210:2013ToxAP.272...37L
4014:2001PNAS...98.5211H
2811:10.1194/jlr.M051169
2460:10.1540/jsmr.41.175
2399:. 116β117: 124β30.
2198:2006CBI...160..204T
2027:2012ToxAP.264...73Y
1299:cerebral infarction
1268:CYP4F2 polymorphism
1006:Blood vessel injury
925:, and a product of
915:smooth muscle cells
371: gΒ·mol
20:
7453:Vernonia tweediana
7032:African blue basil
7004:Bisandrographolide
6590:Steviol glycosides
6543:Hydroxycitronellal
6289:Dehydroligustilide
6109:Angelica acutiloba
6023:Dehydroligustilide
5603:10.2147/OTT.S31586
4387:has generic name (
4061:Nephron Physiology
3783:10.1042/CS20120483
2116:10.1111/acer.12697
1516:metabolic syndrome
1510:Metabolic syndrome
1436:neovascularization
941:compounds such as
593:-inducing agents,
385:Infobox references
18:
7655:
7654:
7633:
7632:
7565:Meclofenamic acid
7371:melegueta peppers
7242:Nonivamide (PAVA)
6978:melegueta peppers
6898:
6897:
6844:
6843:
6756:
6755:
6676:Meclofenamic acid
6599:Stevia rebaudiana
6459:
6458:
6421:Meclofenamic acid
6327:
6326:
6217:melegueta peppers
6190:Phenacyl chloride
6145:N-Methylmaleimide
6135:Methyl salicylate
6080:Hydrogen peroxide
6033:Diallyl disulfide
5895:melegueta peppers
4073:10.1159/000235774
3918:(1 Pt 2): 315β9.
3553:10.1111/jth.12472
2956:10.1172/JCI116709
2562:10.1111/bcp.12086
1396:Isoliquiritigenin
1388:metalloproteinase
1226:gene polymorphism
947:positive feedback
569:, however, is an
465:to 20-HETE by an
393:Chemical compound
391:
390:
248:CompTox Dashboard
115:Interactive image
7685:
7500:Cannabigerovarin
7232:N-Oleoyldopamine
7138:Euodia ruticarpa
7104:Dihydrocapsaicin
6911:
6910:
6907:
6857:
6856:
6853:
6769:
6768:
6765:
6513:Cooling Agent 10
6472:
6471:
6468:
6340:
6339:
6336:
5858:4-Hydroxynonenal
5848:
5847:
5844:
5829:
5820:
5813:
5806:
5797:
5796:
5791:
5790:
5762:
5756:
5755:
5718:
5712:
5711:
5675:
5669:
5668:
5632:
5626:
5625:
5615:
5605:
5581:
5575:
5574:
5564:
5540:
5534:
5533:
5523:
5491:
5485:
5484:
5474:
5450:
5441:
5440:
5404:
5395:
5394:
5384:
5374:
5342:
5336:
5335:
5325:
5315:
5283:
5277:
5276:
5239:
5230:
5229:
5192:
5186:
5185:
5167:
5138:
5132:
5131:
5095:
5089:
5088:
5078:
5046:
5037:
5036:
5007:
5001:
5000:
4963:
4957:
4956:
4928:
4922:
4921:
4911:
4887:
4881:
4880:
4878:
4877:
4871:
4832:
4823:
4817:
4816:
4806:
4782:
4773:
4772:
4736:
4725:
4724:
4706:
4696:
4672:
4663:
4662:
4660:
4659:
4611:
4605:
4604:
4576:
4570:
4569:
4559:
4527:
4518:
4517:
4507:
4483:
4477:
4476:
4466:
4442:
4436:
4435:
4399:
4393:
4392:
4386:
4382:
4380:
4372:
4362:
4330:
4324:
4323:
4313:
4303:
4279:
4273:
4272:
4244:
4238:
4237:
4227:
4217:
4208:(17): 13868β76.
4193:
4187:
4186:
4176:
4165:10.1172/JCI27546
4144:
4138:
4137:
4101:
4095:
4094:
4084:
4052:
4046:
4045:
4035:
4025:
3993:
3987:
3986:
3976:
3944:
3938:
3937:
3927:
3903:
3897:
3896:
3886:
3854:
3848:
3847:
3811:
3805:
3804:
3794:
3771:Clinical Science
3762:
3756:
3755:
3745:
3713:
3707:
3706:
3696:
3664:
3658:
3657:
3640:(11): H1359β67.
3629:
3623:
3622:
3612:
3580:
3574:
3573:
3555:
3531:
3520:
3519:
3509:
3492:(10): 2096β105.
3477:
3466:
3465:
3455:
3423:
3417:
3416:
3380:
3374:
3373:
3344:
3338:
3337:
3327:
3318:(19): 12306β12.
3303:
3297:
3296:
3279:(4): H1194β200.
3268:
3262:
3261:
3232:
3226:
3225:
3215:
3191:
3185:
3184:
3155:
3149:
3148:
3112:
3106:
3105:
3095:
3086:(20): 11658β62.
3071:
3065:
3064:
3054:
3030:
3019:
3018:
3008:
2984:
2978:
2977:
2967:
2935:
2929:
2928:
2918:
2909:(39): 33157β64.
2894:
2883:
2882:
2872:
2840:
2834:
2833:
2823:
2813:
2789:
2783:
2782:
2780:
2779:
2761:
2746:Gastroenterology
2737:
2731:
2730:
2720:
2696:
2690:
2689:
2660:
2654:
2653:
2625:
2619:
2618:
2590:
2584:
2583:
2573:
2541:
2535:
2534:
2524:
2492:
2481:
2480:
2462:
2438:
2427:
2426:
2416:
2388:
2379:
2378:
2368:
2336:
2323:
2322:
2312:
2280:
2274:
2273:
2263:
2231:
2218:
2217:
2180:
2174:
2173:
2137:
2128:
2127:
2098:
2092:
2091:
2063:
2057:
2056:
2046:
2006:
1997:
1996:
1960:
1951:
1950:
1940:
1908:
1895:
1894:
1884:
1852:
1835:
1834:
1824:
1792:
1773:
1772:
1744:
1738:
1737:
1705:
1696:
1695:
1667:
1658:
1657:
1647:
1623:
1614:
1613:
1603:
1571:
1565:
1564:
1536:
1431:MAPK/ERK pathway
1340:CYP2U1 mutations
1190:Other activities
1133:Lewis rats (see
1066:protein kinase C
1060:Renal absorption
977:superoxide anion
939:alpha adrenergic
736:prostaglandin G2
692:) that regulate
605:compounds (e.g.
603:alpha adrenergic
591:vasoconstriction
463:arachidonic acid
421:arachidonic acid
370:
355:
349:
343:
336:Chemical formula
272:
271:
256:
254:
238:
227:
216:
199:
179:
157:
137:
117:
93:
28:
21:
17:
7693:
7692:
7688:
7687:
7686:
7684:
7683:
7682:
7658:
7657:
7656:
7651:
7629:
7620:Tolfenamic acid
7540:Flufenamic acid
7436:
7343:Resiniferatoxin
7336:Ruta graveolens
7099:Diacyl glycerol
6894:
6878:
6840:
6836:
6816:
6802:
6752:
6738:Tolfenamic acid
6731:Ruta graveolens
6671:Flufenamic acid
6634:
6583:Ruta graveolens
6494:(intracellular)
6455:
6451:Tolfenamic acid
6406:Flufenamic acid
6384:
6360:Diacyl glycerol
6323:
6267:
5953:Cannabichromene
5863:4-Oxo-2-nonenal
5835:
5824:
5794:
5763:
5759:
5719:
5715:
5680:Cancer Research
5676:
5672:
5643:(20): 7369β75.
5633:
5629:
5582:
5578:
5555:(10): 3819β24.
5541:
5537:
5492:
5488:
5451:
5444:
5405:
5398:
5343:
5339:
5298:(12): e116247.
5284:
5280:
5240:
5233:
5193:
5189:
5139:
5135:
5096:
5092:
5047:
5040:
5008:
5004:
4964:
4960:
4929:
4925:
4902:(11): 1216β23.
4888:
4884:
4875:
4873:
4869:
4830:
4824:
4820:
4783:
4776:
4737:
4728:
4694:10.1.1.541.9456
4673:
4666:
4657:
4655:
4612:
4608:
4577:
4573:
4528:
4521:
4484:
4480:
4443:
4439:
4400:
4396:
4384:
4383:
4374:
4373:
4331:
4327:
4301:10.1.1.335.1764
4280:
4276:
4245:
4241:
4194:
4190:
4159:(6): 1696β702.
4145:
4141:
4112:(11): 1365β74.
4102:
4098:
4053:
4049:
3994:
3990:
3945:
3941:
3904:
3900:
3855:
3851:
3812:
3808:
3777:(12): 695β700.
3763:
3759:
3714:
3710:
3665:
3661:
3630:
3626:
3581:
3577:
3532:
3523:
3478:
3469:
3424:
3420:
3381:
3377:
3356:(3): H1089β95.
3345:
3341:
3304:
3300:
3269:
3265:
3233:
3229:
3192:
3188:
3156:
3152:
3113:
3109:
3072:
3068:
3031:
3022:
2985:
2981:
2936:
2932:
2895:
2886:
2841:
2837:
2804:(11): 2334β42.
2790:
2786:
2777:
2775:
2738:
2734:
2711:(11): 1215β22.
2697:
2693:
2661:
2657:
2626:
2622:
2591:
2587:
2542:
2538:
2493:
2484:
2439:
2430:
2389:
2382:
2337:
2326:
2281:
2277:
2232:
2221:
2181:
2177:
2138:
2131:
2099:
2095:
2064:
2060:
2007:
2000:
1961:
1954:
1909:
1898:
1867:(12): 1429β40.
1853:
1838:
1793:
1776:
1745:
1741:
1720:(2): H1018β26.
1706:
1699:
1678:(12): 2263β75.
1668:
1661:
1624:
1617:
1572:
1568:
1537:
1528:
1524:
1512:
1496:
1482:
1444:
1368:
1363:
1342:
1270:
1258:ischemic stroke
1214:
1209:
1207:Genetic studies
1204:
1192:
1152:
1144:
1119:sodium chloride
1115:
1099:
1090:
1062:
1025:
1008:
1002:-activation .
911:
906:
901:
885:
784:12-lipoxygenase
717:Glucuronidation
714:
706:Coeliac disease
702:Krohn's disease
662:
617:carbon monoxide
583:
555:
517:stereoisomers.
467:omega oxidation
451:Cytochrome P450
447:
442:
425:vascular system
394:
387:
382:
368:
358:
352:
346:
338:
324:
321:
316:
315:
304:
301:
300:
294:
293:
287:
286:
275:
265:DTXSID601009895
257:
250:
241:
228:
202:
182:
169:
160:
140:
120:
107:
96:
83:
69:
61:
60:
12:
11:
5:
7691:
7681:
7680:
7675:
7670:
7653:
7652:
7638:
7635:
7634:
7631:
7630:
7628:
7627:
7622:
7617:
7612:
7607:
7602:
7597:
7592:
7587:
7582:
7577:
7572:
7567:
7562:
7557:
7552:
7547:
7542:
7537:
7532:
7527:
7522:
7517:
7507:
7497:
7487:
7477:
7472:
7467:
7462:
7457:
7444:
7442:
7438:
7437:
7435:
7434:
7429:
7419:
7414:
7398:
7384:
7374:
7356:
7340:
7328:
7323:
7318:
7313:
7310:Dorrigo pepper
7303:
7289:
7282:Phorbol esters
7279:
7274:
7269:
7259:
7249:
7239:
7234:
7229:
7224:
7214:
7207:
7202:
7192:
7182:
7172:
7167:
7162:
7157:
7152:
7142:
7130:
7116:
7111:
7101:
7096:
7091:
7069:
7059:
7052:Cannabidivarin
7049:
7039:
7020:camphor laurel
7013:
7001:
6996:
6991:
6981:
6963:
6958:
6953:
6948:
6943:
6938:
6933:
6928:
6923:
6917:
6915:
6908:
6900:
6899:
6896:
6895:
6893:
6892:
6886:
6884:
6880:
6879:
6877:
6876:
6863:
6861:
6854:
6846:
6845:
6842:
6841:
6839:
6838:
6834:
6830:
6824:
6822:
6818:
6817:
6815:
6814:
6809:
6804:
6800:
6796:
6791:
6786:
6781:
6775:
6773:
6766:
6758:
6757:
6754:
6753:
6751:
6750:
6745:
6740:
6735:
6723:
6718:
6713:
6708:
6703:
6698:
6688:
6683:
6681:Mefenamic acid
6678:
6673:
6668:
6663:
6658:
6653:
6648:
6642:
6640:
6636:
6635:
6633:
6632:
6627:
6622:
6603:
6587:
6575:
6570:
6565:
6555:
6550:
6545:
6540:
6535:
6530:
6525:
6515:
6510:
6505:
6500:
6495:
6489:
6484:
6478:
6476:
6469:
6461:
6460:
6457:
6456:
6454:
6453:
6448:
6443:
6438:
6433:
6428:
6423:
6418:
6413:
6408:
6403:
6398:
6392:
6390:
6386:
6385:
6383:
6382:
6377:
6374:St John's wort
6367:
6362:
6357:
6354:St John's wort
6346:
6344:
6337:
6329:
6328:
6325:
6324:
6322:
6321:
6316:
6311:
6301:
6296:
6286:
6281:
6275:
6273:
6269:
6268:
6266:
6265:
6260:
6250:
6240:
6235:
6225:
6220:
6202:
6199:Dorrigo pepper
6192:
6187:
6182:
6177:
6167:
6157:
6147:
6142:
6132:
6127:
6120:Sichuan pepper
6113:
6097:
6092:
6090:Isothiocyanate
6087:
6082:
6077:
6072:
6067:
6057:
6052:
6047:
6035:
6030:
6020:
6010:
6000:
5995:
5990:
5983:Cinnamaldehyde
5980:
5970:
5960:
5950:
5945:
5940:
5935:
5913:
5903:
5898:
5880:
5875:
5870:
5865:
5860:
5854:
5852:
5845:
5837:
5836:
5823:
5822:
5815:
5808:
5800:
5793:
5792:
5757:
5713:
5686:(7): 2357β64.
5670:
5627:
5576:
5535:
5486:
5442:
5396:
5357:(12): e15647.
5337:
5278:
5231:
5187:
5133:
5090:
5061:(6): 1051β64.
5038:
5002:
4958:
4923:
4882:
4818:
4797:(9): 1719β26.
4774:
4747:(2): 1677β82.
4726:
4664:
4626:(3β4): 75β85.
4606:
4571:
4519:
4478:
4437:
4394:
4345:(8): 1606β12.
4325:
4274:
4239:
4188:
4139:
4096:
4047:
3988:
3959:(8): 1288β96.
3939:
3898:
3849:
3822:(10): 1031β8.
3806:
3757:
3728:(3): R248β51.
3708:
3679:(6): R1543β8.
3659:
3624:
3575:
3521:
3467:
3418:
3375:
3339:
3298:
3263:
3227:
3206:(4): 2648β56.
3186:
3150:
3107:
3066:
3020:
2999:(12): 8501β7.
2979:
2950:(3): 1357β65.
2930:
2884:
2835:
2784:
2732:
2691:
2655:
2620:
2585:
2556:(4): 587β602.
2536:
2482:
2428:
2380:
2351:(1β4): 45β53.
2324:
2275:
2219:
2175:
2142:Histopathology
2129:
2093:
2058:
1998:
1952:
1896:
1836:
1774:
1739:
1697:
1659:
1638:(8): 6305β14.
1615:
1566:
1525:
1523:
1520:
1511:
1508:
1504:thromboxane A2
1495:
1492:
1481:
1478:
1443:
1440:
1367:
1364:
1362:
1359:
1341:
1338:
1269:
1266:
1262:genetic marker
1213:
1210:
1208:
1205:
1203:
1200:
1191:
1188:
1151:
1148:
1143:
1140:
1135:Laboratory rat
1114:
1111:
1098:
1095:
1089:
1086:
1061:
1058:
1024:
1021:
1011:Sprague Dawley
1007:
1004:
988:thromboxane A2
943:norepinephrine
910:
907:
905:
904:Rodent studies
902:
900:
897:
884:
881:
876:Beta oxidation
744:thromboxane B2
740:thromboxane A2
732:cyclooxygenase
719:of 20-HETE by
713:
710:
690:prostaglandins
688:, and several
661:
658:
651:, and various
607:norepinephrine
595:angiotensin II
582:
579:
560:rodent studies
554:
551:
446:
443:
441:
438:
419:metabolite of
392:
389:
388:
383:
379:standard state
376:
373:
372:
366:
360:
359:
356:
350:
344:
339:
334:
331:
330:
326:
325:
323:
322:
319:
311:
310:
309:
306:
305:
303:
302:
298:
297:
295:
291:
290:
282:
281:
280:
277:
276:
274:
273:
260:
258:
246:
243:
242:
240:
239:
231:
229:
221:
218:
217:
210:
204:
203:
201:
200:
192:
190:
184:
183:
181:
180:
172:
170:
165:
162:
161:
159:
158:
150:
148:
142:
141:
139:
138:
130:
128:
122:
121:
119:
118:
110:
108:
101:
98:
97:
95:
94:
86:
84:
79:
76:
75:
71:
70:
67:
63:
62:
42:
41:
35:
34:
30:
29:
9:
6:
4:
3:
2:
7690:
7679:
7676:
7674:
7671:
7669:
7666:
7665:
7663:
7650:
7649:
7645:
7642:
7636:
7626:
7623:
7621:
7618:
7616:
7613:
7611:
7608:
7606:
7603:
7601:
7600:Ruthenium red
7598:
7596:
7593:
7591:
7588:
7586:
7583:
7581:
7580:Niflumic acid
7578:
7576:
7573:
7571:
7568:
7566:
7563:
7561:
7558:
7556:
7553:
7551:
7548:
7546:
7543:
7541:
7538:
7536:
7533:
7531:
7528:
7526:
7523:
7521:
7518:
7515:
7511:
7508:
7505:
7501:
7498:
7495:
7491:
7488:
7485:
7481:
7478:
7476:
7473:
7471:
7468:
7466:
7463:
7461:
7458:
7455:
7454:
7449:
7448:Ξ±-Spinasterol
7446:
7445:
7443:
7439:
7433:
7430:
7427:
7423:
7420:
7418:
7415:
7412:
7411:
7407:
7402:
7399:
7396:
7392:
7388:
7385:
7382:
7378:
7375:
7372:
7368:
7364:
7360:
7357:
7354:
7353:
7349:
7344:
7341:
7338:
7337:
7332:
7329:
7327:
7324:
7322:
7319:
7317:
7314:
7311:
7307:
7304:
7301:
7297:
7293:
7290:
7287:
7283:
7280:
7278:
7275:
7273:
7270:
7267:
7263:
7260:
7257:
7253:
7250:
7247:
7243:
7240:
7238:
7235:
7233:
7230:
7228:
7225:
7222:
7218:
7215:
7212:
7208:
7206:
7203:
7200:
7196:
7193:
7190:
7186:
7183:
7180:
7176:
7175:Homocapsaicin
7173:
7171:
7168:
7166:
7163:
7161:
7158:
7156:
7153:
7150:
7146:
7143:
7140:
7139:
7134:
7131:
7128:
7124:
7120:
7117:
7115:
7112:
7109:
7105:
7102:
7100:
7097:
7095:
7092:
7089:
7088:wild bergamot
7085:
7081:
7077:
7073:
7070:
7067:
7063:
7060:
7057:
7053:
7050:
7047:
7043:
7040:
7037:
7036:camphor basil
7033:
7029:
7025:
7021:
7017:
7014:
7011:
7010:
7005:
7002:
7000:
6997:
6995:
6992:
6989:
6985:
6982:
6979:
6975:
6971:
6967:
6964:
6962:
6959:
6957:
6954:
6952:
6949:
6947:
6944:
6942:
6939:
6937:
6934:
6932:
6929:
6927:
6924:
6922:
6919:
6918:
6916:
6912:
6909:
6906:
6901:
6891:
6890:Ruthenium red
6888:
6887:
6885:
6881:
6874:
6873:
6868:
6865:
6864:
6862:
6858:
6855:
6852:
6847:
6837:
6831:
6829:
6826:
6825:
6823:
6819:
6813:
6810:
6808:
6805:
6803:
6797:
6795:
6792:
6790:
6787:
6785:
6782:
6780:
6777:
6776:
6774:
6770:
6767:
6764:
6759:
6749:
6746:
6744:
6741:
6739:
6736:
6733:
6732:
6727:
6724:
6722:
6721:Ruthenium red
6719:
6717:
6714:
6712:
6709:
6707:
6704:
6702:
6701:Niflumic acid
6699:
6696:
6692:
6689:
6687:
6684:
6682:
6679:
6677:
6674:
6672:
6669:
6667:
6664:
6662:
6659:
6657:
6654:
6652:
6649:
6647:
6644:
6643:
6641:
6637:
6631:
6628:
6626:
6623:
6621:; indirectly)
6620:
6616:
6612:
6608:
6604:
6601:
6600:
6595:
6591:
6588:
6585:
6584:
6579:
6576:
6574:
6571:
6569:
6566:
6563:
6559:
6556:
6554:
6551:
6549:
6546:
6544:
6541:
6539:
6536:
6534:
6531:
6529:
6528:Frescolat MGA
6526:
6523:
6519:
6516:
6514:
6511:
6509:
6506:
6504:
6501:
6499:
6496:
6493:
6490:
6488:
6485:
6483:
6480:
6479:
6477:
6473:
6470:
6467:
6462:
6452:
6449:
6447:
6444:
6442:
6439:
6437:
6434:
6432:
6431:Niflumic acid
6429:
6427:
6424:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6393:
6391:
6387:
6381:
6378:
6375:
6371:
6368:
6366:
6363:
6361:
6358:
6355:
6351:
6348:
6347:
6345:
6341:
6338:
6335:
6330:
6320:
6319:Ruthenium red
6317:
6315:
6312:
6309:
6305:
6302:
6300:
6297:
6294:
6290:
6287:
6285:
6282:
6280:
6277:
6276:
6274:
6270:
6264:
6261:
6258:
6254:
6251:
6248:
6244:
6241:
6239:
6236:
6233:
6229:
6226:
6224:
6221:
6218:
6214:
6210:
6206:
6203:
6200:
6196:
6193:
6191:
6188:
6186:
6183:
6181:
6178:
6175:
6171:
6168:
6165:
6161:
6158:
6155:
6151:
6148:
6146:
6143:
6140:
6136:
6133:
6131:
6130:Methylglyoxal
6128:
6125:
6121:
6117:
6114:
6111:
6110:
6105:
6101:
6098:
6096:
6093:
6091:
6088:
6086:
6083:
6081:
6078:
6076:
6073:
6071:
6068:
6065:
6061:
6058:
6056:
6053:
6051:
6048:
6045:
6044:
6039:
6036:
6034:
6031:
6028:
6024:
6021:
6018:
6014:
6011:
6008:
6004:
6003:Cuminaldehyde
6001:
5999:
5996:
5994:
5991:
5988:
5984:
5981:
5978:
5974:
5971:
5968:
5964:
5961:
5958:
5954:
5951:
5949:
5946:
5944:
5941:
5939:
5936:
5933:
5929:
5925:
5921:
5917:
5914:
5911:
5907:
5904:
5902:
5899:
5896:
5892:
5888:
5884:
5881:
5879:
5876:
5874:
5871:
5869:
5866:
5864:
5861:
5859:
5856:
5855:
5853:
5849:
5846:
5843:
5838:
5834:
5831:
5821:
5816:
5814:
5809:
5807:
5802:
5801:
5798:
5788:
5784:
5780:
5776:
5773:(2): 263β70.
5772:
5768:
5761:
5753:
5749:
5745:
5741:
5737:
5733:
5730:(2): 526β33.
5729:
5725:
5717:
5709:
5705:
5701:
5697:
5693:
5689:
5685:
5681:
5674:
5666:
5662:
5658:
5654:
5650:
5646:
5642:
5638:
5631:
5623:
5619:
5614:
5609:
5604:
5599:
5595:
5591:
5587:
5580:
5572:
5568:
5563:
5558:
5554:
5550:
5546:
5539:
5531:
5527:
5522:
5517:
5513:
5509:
5506:(3): 619β29.
5505:
5501:
5497:
5490:
5482:
5478:
5473:
5468:
5464:
5460:
5456:
5449:
5447:
5438:
5434:
5430:
5426:
5422:
5418:
5415:(1): 105β18.
5414:
5410:
5403:
5401:
5392:
5388:
5383:
5378:
5373:
5368:
5364:
5360:
5356:
5352:
5348:
5341:
5333:
5329:
5324:
5319:
5314:
5309:
5305:
5301:
5297:
5293:
5289:
5282:
5274:
5270:
5266:
5262:
5258:
5254:
5250:
5246:
5238:
5236:
5227:
5223:
5219:
5215:
5211:
5207:
5203:
5199:
5191:
5183:
5179:
5175:
5171:
5166:
5161:
5157:
5153:
5150:(2): 373β81.
5149:
5145:
5137:
5129:
5125:
5121:
5117:
5113:
5109:
5106:(1): 99β110.
5105:
5101:
5094:
5086:
5082:
5077:
5072:
5068:
5064:
5060:
5056:
5052:
5045:
5043:
5034:
5030:
5026:
5022:
5018:
5014:
5006:
4998:
4994:
4990:
4986:
4982:
4978:
4975:(4): 369β74.
4974:
4970:
4962:
4954:
4950:
4946:
4942:
4938:
4934:
4927:
4919:
4915:
4910:
4905:
4901:
4897:
4893:
4886:
4868:
4864:
4860:
4856:
4852:
4848:
4844:
4840:
4836:
4829:
4822:
4814:
4810:
4805:
4800:
4796:
4792:
4788:
4781:
4779:
4770:
4766:
4762:
4758:
4754:
4750:
4746:
4742:
4735:
4733:
4731:
4722:
4718:
4714:
4710:
4705:
4700:
4695:
4690:
4687:(2): 373β80.
4686:
4682:
4678:
4671:
4669:
4653:
4649:
4645:
4641:
4637:
4633:
4629:
4625:
4621:
4617:
4610:
4602:
4598:
4594:
4590:
4586:
4582:
4575:
4567:
4563:
4558:
4553:
4549:
4545:
4542:(3): 187β94.
4541:
4537:
4533:
4526:
4524:
4515:
4511:
4506:
4501:
4498:(6): 1142β8.
4497:
4493:
4489:
4482:
4474:
4470:
4465:
4460:
4457:(4): 766β71.
4456:
4452:
4448:
4441:
4433:
4429:
4425:
4421:
4417:
4413:
4410:(3): 453β61.
4409:
4405:
4398:
4390:
4385:|first8=
4378:
4370:
4366:
4361:
4356:
4352:
4348:
4344:
4340:
4336:
4329:
4321:
4317:
4312:
4307:
4302:
4297:
4293:
4289:
4285:
4278:
4270:
4266:
4262:
4258:
4255:(10): 893β9.
4254:
4250:
4243:
4235:
4231:
4226:
4221:
4216:
4211:
4207:
4203:
4199:
4192:
4184:
4180:
4175:
4170:
4166:
4162:
4158:
4154:
4150:
4143:
4135:
4131:
4127:
4123:
4119:
4115:
4111:
4107:
4100:
4092:
4088:
4083:
4078:
4074:
4070:
4066:
4062:
4058:
4051:
4043:
4039:
4034:
4029:
4024:
4019:
4015:
4011:
4008:(9): 5211β6.
4007:
4003:
3999:
3992:
3984:
3980:
3975:
3970:
3966:
3962:
3958:
3954:
3950:
3943:
3935:
3931:
3926:
3921:
3917:
3913:
3909:
3902:
3894:
3890:
3885:
3880:
3876:
3872:
3869:(4): F771β9.
3868:
3864:
3860:
3853:
3845:
3841:
3837:
3833:
3829:
3825:
3821:
3817:
3810:
3802:
3798:
3793:
3788:
3784:
3780:
3776:
3772:
3768:
3761:
3753:
3749:
3744:
3739:
3735:
3731:
3727:
3723:
3719:
3712:
3704:
3700:
3695:
3690:
3686:
3682:
3678:
3674:
3670:
3663:
3655:
3651:
3647:
3643:
3639:
3635:
3628:
3620:
3616:
3611:
3606:
3602:
3598:
3594:
3590:
3586:
3579:
3571:
3567:
3563:
3559:
3554:
3549:
3546:(2): 126β37.
3545:
3541:
3537:
3530:
3528:
3526:
3517:
3513:
3508:
3503:
3499:
3495:
3491:
3487:
3483:
3476:
3474:
3472:
3463:
3459:
3454:
3449:
3445:
3441:
3437:
3433:
3429:
3422:
3414:
3410:
3406:
3402:
3398:
3394:
3390:
3386:
3379:
3371:
3367:
3363:
3359:
3355:
3351:
3343:
3335:
3331:
3326:
3321:
3317:
3313:
3309:
3302:
3294:
3290:
3286:
3282:
3278:
3274:
3267:
3259:
3255:
3251:
3247:
3244:(5): 249β53.
3243:
3239:
3231:
3223:
3219:
3214:
3209:
3205:
3201:
3197:
3190:
3182:
3178:
3174:
3170:
3167:(3): 175β81.
3166:
3162:
3154:
3146:
3142:
3138:
3134:
3130:
3126:
3123:(4): 438β43.
3122:
3118:
3111:
3103:
3099:
3094:
3089:
3085:
3081:
3077:
3070:
3062:
3058:
3053:
3048:
3045:(5): 1393β8.
3044:
3040:
3036:
3029:
3027:
3025:
3016:
3012:
3007:
3002:
2998:
2994:
2990:
2983:
2975:
2971:
2966:
2961:
2957:
2953:
2949:
2945:
2941:
2934:
2926:
2922:
2917:
2912:
2908:
2904:
2900:
2893:
2891:
2889:
2880:
2876:
2871:
2866:
2862:
2858:
2855:(2): 267β74.
2854:
2850:
2846:
2839:
2831:
2827:
2822:
2817:
2812:
2807:
2803:
2799:
2795:
2788:
2773:
2769:
2765:
2760:
2755:
2752:(4): 929β31.
2751:
2747:
2743:
2736:
2728:
2724:
2719:
2714:
2710:
2706:
2702:
2695:
2687:
2683:
2679:
2675:
2671:
2667:
2659:
2651:
2647:
2643:
2639:
2636:(1): 210β22.
2635:
2631:
2624:
2616:
2612:
2608:
2604:
2600:
2596:
2589:
2581:
2577:
2572:
2567:
2563:
2559:
2555:
2551:
2547:
2540:
2532:
2528:
2523:
2518:
2514:
2510:
2506:
2502:
2498:
2491:
2489:
2487:
2478:
2474:
2470:
2466:
2461:
2456:
2453:(4): 175β93.
2452:
2448:
2444:
2437:
2435:
2433:
2424:
2420:
2415:
2410:
2406:
2402:
2398:
2394:
2387:
2385:
2376:
2372:
2367:
2362:
2358:
2354:
2350:
2346:
2342:
2335:
2333:
2331:
2329:
2320:
2316:
2311:
2306:
2302:
2298:
2295:(2): 109β18.
2294:
2290:
2286:
2279:
2271:
2267:
2262:
2257:
2253:
2249:
2245:
2241:
2237:
2230:
2228:
2226:
2224:
2215:
2211:
2207:
2203:
2199:
2195:
2192:(3): 204β16.
2191:
2187:
2179:
2171:
2167:
2163:
2159:
2155:
2151:
2148:(2): 202β11.
2147:
2143:
2136:
2134:
2125:
2121:
2117:
2113:
2109:
2105:
2097:
2089:
2085:
2081:
2077:
2074:(2): 105β10.
2073:
2069:
2062:
2054:
2050:
2045:
2040:
2036:
2032:
2028:
2024:
2020:
2016:
2012:
2005:
2003:
1994:
1990:
1986:
1982:
1978:
1974:
1970:
1966:
1959:
1957:
1948:
1944:
1939:
1934:
1930:
1926:
1922:
1918:
1914:
1907:
1905:
1903:
1901:
1892:
1888:
1883:
1878:
1874:
1870:
1866:
1862:
1858:
1851:
1849:
1847:
1845:
1843:
1841:
1832:
1828:
1823:
1818:
1814:
1810:
1806:
1802:
1798:
1791:
1789:
1787:
1785:
1783:
1781:
1779:
1770:
1766:
1762:
1758:
1754:
1750:
1743:
1735:
1731:
1727:
1723:
1719:
1715:
1711:
1704:
1702:
1693:
1689:
1685:
1681:
1677:
1673:
1666:
1664:
1655:
1651:
1646:
1641:
1637:
1633:
1629:
1622:
1620:
1611:
1607:
1602:
1597:
1593:
1589:
1586:(4): 723β35.
1585:
1581:
1577:
1570:
1562:
1558:
1554:
1550:
1546:
1542:
1535:
1533:
1531:
1526:
1519:
1517:
1507:
1505:
1501:
1491:
1488:
1477:
1474:
1468:
1464:
1462:
1458:
1454:
1449:
1442:Other cancers
1439:
1437:
1432:
1428:
1424:
1420:
1416:
1411:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1377:
1373:
1366:Breast cancer
1358:
1355:
1351:
1347:
1337:
1335:
1331:
1326:
1324:
1320:
1315:
1313:
1310:responses to
1309:
1304:
1300:
1295:
1292:
1288:
1284:
1280:
1276:
1265:
1263:
1259:
1255:
1251:
1247:
1242:
1238:
1236:
1232:
1227:
1222:
1220:
1219:gene knockout
1202:Human studies
1199:
1197:
1187:
1185:
1181:
1177:
1171:
1169:
1165:
1164:gene knockout
1160:
1157:
1147:
1139:
1136:
1131:
1129:
1124:
1120:
1110:
1108:
1103:
1094:
1085:
1083:
1079:
1075:
1071:
1070:Na+/K+-ATPase
1067:
1057:
1054:
1050:
1046:
1042:
1038:
1034:
1030:
1020:
1017:
1012:
1003:
1001:
997:
991:
989:
985:
980:
978:
974:
970:
966:
961:
959:
955:
950:
948:
944:
940:
936:
932:
928:
924:
920:
916:
896:
894:
889:
880:
877:
873:
869:
865:
861:
857:
853:
849:
845:
841:
837:
833:
828:
825:
821:
817:
813:
809:
805:
801:
797:
793:
789:
785:
781:
777:
773:
769:
765:
761:
757:
753:
749:
745:
741:
737:
733:
729:
724:
722:
718:
709:
707:
703:
699:
695:
691:
687:
683:
679:
675:
671:
667:
657:
654:
650:
646:
642:
638:
634:
630:
626:
622:
618:
614:
610:
608:
604:
600:
596:
592:
588:
578:
576:
572:
568:
563:
561:
550:
548:
544:
540:
536:
531:
527:
523:
518:
516:
512:
508:
504:
500:
495:
493:
489:
485:
481:
477:
473:
468:
464:
461:, metabolize
460:
456:
452:
437:
435:
431:
426:
422:
418:
414:
410:
406:
402:
398:
386:
380:
374:
367:
365:
362:
361:
340:
337:
333:
332:
327:
318:
317:
314:
307:
296:
289:
288:
285:
278:
270:
266:
262:
261:
259:
249:
245:
244:
237:
233:
232:
230:
224:
220:
219:
215:
211:
209:
206:
205:
198:
194:
193:
191:
189:
186:
185:
178:
174:
173:
171:
168:
164:
163:
156:
152:
151:
149:
147:
144:
143:
136:
132:
131:
129:
127:
124:
123:
116:
112:
111:
109:
105:
100:
99:
92:
88:
87:
85:
82:
78:
77:
72:
64:
58:
54:
50:
46:
40:
36:
31:
27:
22:
16:
7668:Cell biology
7640:
7639:
7480:Cannabigerol
7451:
7404:
7346:
7334:
7296:black pepper
7256:chili pepper
7189:chili pepper
7179:chili pepper
7170:Hepoxilin B3
7165:Hepoxilin A3
7136:
7108:chili pepper
7066:chili pepper
7007:
6960:
6870:
6729:
6656:Clotrimazole
6597:
6581:
6533:Frescolat ML
6441:Progesterone
6350:Adhyperforin
6263:WIN 55,212-2
6256:
6107:
6075:Hepoxilin B3
6070:Hepoxilin A3
6041:
5973:Cannabigerol
5770:
5766:
5760:
5727:
5723:
5716:
5683:
5679:
5673:
5640:
5636:
5630:
5593:
5589:
5579:
5552:
5548:
5538:
5503:
5499:
5489:
5465:(4): 163β9.
5462:
5458:
5412:
5408:
5354:
5350:
5340:
5295:
5291:
5281:
5251:(1): 10β20.
5248:
5244:
5204:(1): 37β48.
5201:
5197:
5190:
5147:
5143:
5136:
5103:
5099:
5093:
5058:
5054:
5016:
5012:
5005:
4972:
4968:
4961:
4939:(3): 145β7.
4936:
4932:
4926:
4899:
4895:
4885:
4874:. Retrieved
4838:
4834:
4821:
4794:
4790:
4744:
4740:
4684:
4681:Hypertension
4680:
4656:. Retrieved
4623:
4619:
4609:
4587:(1): 74β81.
4584:
4580:
4574:
4539:
4535:
4495:
4492:Hypertension
4491:
4481:
4454:
4451:Hypertension
4450:
4440:
4407:
4403:
4397:
4377:cite journal
4342:
4338:
4328:
4291:
4287:
4277:
4252:
4248:
4242:
4205:
4201:
4191:
4156:
4152:
4142:
4109:
4105:
4099:
4064:
4060:
4050:
4005:
4001:
3991:
3956:
3952:
3942:
3915:
3912:Hypertension
3911:
3901:
3866:
3862:
3852:
3819:
3815:
3809:
3774:
3770:
3760:
3725:
3721:
3711:
3676:
3672:
3662:
3637:
3633:
3627:
3595:(1): 67β74.
3592:
3588:
3578:
3543:
3539:
3489:
3485:
3438:(1): 43β54.
3435:
3431:
3421:
3391:(2): 210β6.
3388:
3385:Hypertension
3384:
3378:
3353:
3349:
3342:
3315:
3311:
3301:
3276:
3272:
3266:
3241:
3237:
3230:
3203:
3199:
3189:
3164:
3160:
3153:
3120:
3116:
3110:
3083:
3079:
3069:
3042:
3039:Hypertension
3038:
2996:
2992:
2982:
2947:
2943:
2933:
2906:
2902:
2852:
2848:
2838:
2801:
2797:
2787:
2776:. Retrieved
2749:
2745:
2735:
2708:
2704:
2694:
2672:(2): 201β5.
2669:
2665:
2658:
2633:
2629:
2623:
2598:
2594:
2588:
2553:
2549:
2539:
2507:(1): 37β46.
2504:
2500:
2450:
2446:
2396:
2348:
2344:
2292:
2288:
2278:
2243:
2239:
2189:
2185:
2178:
2145:
2141:
2110:(5): 790β7.
2107:
2103:
2096:
2071:
2067:
2061:
2021:(1): 73β83.
2018:
2014:
1971:(2): 63β71.
1968:
1964:
1920:
1916:
1864:
1860:
1804:
1800:
1755:(1): 55β68.
1752:
1748:
1742:
1717:
1713:
1675:
1671:
1635:
1631:
1583:
1579:
1569:
1544:
1540:
1513:
1497:
1483:
1469:
1465:
1445:
1412:
1380:transfection
1369:
1354:mitochondria
1343:
1333:
1327:
1316:
1296:
1290:
1286:
1282:
1278:
1271:
1243:
1239:
1223:
1215:
1193:
1176:vasodilation
1172:
1161:
1153:
1145:
1132:
1116:
1100:
1091:
1088:Hypertension
1063:
1026:
1009:
996:hypertension
992:
981:
971:(eNOS) with
965:nitric oxide
962:
951:
912:
890:
886:
871:
867:
863:
859:
855:
851:
847:
843:
839:
835:
831:
829:
819:
815:
811:
807:
803:
799:
795:
791:
787:
779:
775:
771:
767:
763:
759:
755:
751:
747:
725:
715:
694:inflammation
663:
613:Nitric oxide
611:
584:
564:
556:
519:
514:
510:
506:
503:stereoisomer
498:
496:
483:
479:
475:
471:
449:A subset of
448:
440:Biosynthesis
412:
408:
404:
400:
396:
395:
74:Identifiers
66:Other names
56:
52:
48:
44:
15:
7678:Eicosanoids
7673:Fatty acids
7615:Tivanisiran
7520:Capsazepine
7432:Zucapsaicin
7300:long pepper
7266:Pacific yew
7155:GSK1016790A
7042:Cannabidiol
7028:camphorweed
6716:RQ-00203078
6711:PF-05105679
6651:Capsazepine
6416:GSK2293017A
6380:Substance P
6365:GSK1702934A
6314:PF-04745637
6253:Umbellulone
6174:Pacific yew
6160:Oleocanthal
6139:wintergreen
6100:Ligustilide
5963:Cannabidiol
5928:horseradish
5165:2434/421160
4294:(1): 63β9.
4288:Circulation
4067:(4): 23β8.
3117:Circulation
2289:Xenobiotica
1923:(1): 1β12.
1494:Vasculature
1312:epinephrine
1252:(SNP) (see
1128:vasopressin
919:vasopressin
893:neutrophils
786:to form 12(
700:with human
666:lauric acid
641:gemfibrozil
599:endothelins
571:epoxygenase
329:Properties
135:CHEBI:34306
7662:Categories
7510:Cannabinol
7410:pooissonii
7401:Tinyatoxin
7352:pooissonii
7316:Probenecid
7306:Polygodial
7262:Paclitaxel
7246:PAVA spray
7133:Evodiamine
7084:pepperwort
6999:Anandamide
6966:Ξ±-Sanshool
6914:Activators
6867:Triptolide
6860:Activators
6772:Activators
6748:TRPM4-IN-5
6666:Elismetrep
6594:stevioside
6522:eucalyptus
6518:Eucalyptol
6482:ADP-ribose
6475:Activators
6411:GSK417651A
6370:Hyperforin
6343:Activators
6223:Tear gases
6195:Polygodial
6185:PF-4840154
6170:Paclitaxel
6038:Dicentrine
5948:Bradykinin
5883:Ξ±-Sanshool
5851:Activators
5833:modulators
5596:: 243β55.
4876:2020-05-24
4658:2018-08-27
2778:2019-08-16
2601:: 413β38.
1547:: 413β38.
1522:References
1419:Pseudogene
1400:MDA-MB-231
1235:Odds ratio
1156:transgenic
1037:Thrombosis
1033:thrombosis
923:endothelin
746:and to 11(
712:Metabolism
621:superoxide
577:products.
417:eicosanoid
364:Molar mass
167:IUPHAR/BPS
146:ChemSpider
102:3D model (
91:79551-86-3
81:CAS Number
7641:See also:
7625:TRPV3-74a
7610:SB-705498
7605:SB-366791
7555:Lanthanum
7550:HC-067047
7470:Asivatrep
7331:Rutamarin
7195:Incensole
7145:Gingerols
7114:Estradiol
7090:, others)
7072:Carvacrol
7062:Capsaicin
6956:13-oxoODE
6946:12S-HpETE
6926:5',6'-EET
6726:Rutamarin
6625:Thio-BCTC
6578:Rutamarin
6508:Coolact P
6299:HC-030031
6164:olive oil
6060:Gingerols
5873:12S-HpETE
4689:CiteSeerX
4296:CiteSeerX
1408:apoptosis
1350:orthologs
1246:haplotype
935:Androgens
824:chirality
728:platelets
587:Androgens
455:microsome
453:(CYP450)
7575:NGD-8243
7560:Mavatrep
7545:GRC-6211
7514:cannabis
7504:cannabis
7494:cannabis
7484:cannabis
7465:AMG-9810
7441:Blockers
7422:Vanillin
7417:Tramadol
7381:cannabis
7359:Shogaols
7292:Piperine
7056:cannabis
7046:cannabis
7024:rosemary
6941:12S-HETE
6936:9-oxoODE
6883:Blockers
6833:PI(4,5)P
6821:Blockers
6799:PI(3,5)P
6706:Ononetin
6691:Nicotine
6639:Blockers
6615:fructose
6607:tastants
6553:Linalool
6538:Geraniol
6498:CIM-0216
6389:Blockers
6304:Nicotine
6279:A-967079
6272:Blockers
6232:cannabis
6205:Shogaols
6150:Nicotine
6116:Linalool
6055:Formalin
6017:turmeric
6013:Curcumin
5987:cinnamon
5977:cannabis
5967:cannabis
5957:cannabis
5943:ASP-7663
5901:Acrolein
5787:19013235
5752:21503433
5744:16081682
5700:15059886
5665:37734580
5657:16243809
5622:23569388
5571:19846914
5530:21120482
5481:22798501
5437:11952881
5429:25701119
5391:21209903
5351:PLOS ONE
5332:25549350
5292:PLOS ONE
5273:25094029
5226:23747687
5182:19189811
5174:24337409
5128:13728834
5120:25178427
5085:23176821
5033:29628049
5019:: 6β13.
4997:34470511
4989:24418943
4953:19097922
4918:18787519
4867:Archived
4855:24984178
4813:18971550
4769:14217802
4761:21625857
4713:18574070
4652:Archived
4640:22173545
4601:17341693
4566:20130494
4514:18936345
4473:16144986
4432:23680415
4424:18300855
4369:18385420
4320:15611369
4234:22389490
4183:16691295
4126:20943934
4091:19713718
4042:11320253
3983:23641057
3893:19211690
3844:30640395
3801:23438293
3752:23220478
3703:21474427
3654:25820395
3619:23658377
3570:26569858
3562:24298905
3516:21610722
3462:27492226
3405:15226275
3370:15130884
3293:21239640
3222:14612451
3181:10841040
3137:15262846
3061:18391101
3015:10722687
2925:16081420
2830:25249502
2772:Archived
2768:24406470
2727:16835590
2650:20869469
2615:15822183
2580:23362865
2531:25427230
2469:16258232
2423:25526688
2375:21722750
2319:20021200
2270:25986599
2246:: 40β9.
2214:16527260
2162:20716162
2124:25872594
2088:20630735
2053:22841774
1985:22706230
1947:23584425
1891:23688133
1831:25813407
1807:: 9β16.
1734:18156192
1710:Falck JR
1692:18433732
1654:14660610
1610:20941528
1561:15822183
1500:receptor
1248:tagging
1154:Cyp4a12-
984:receptor
649:propanol
7595:RN-9893
7590:RN-1734
7460:AMG-517
7426:vanilla
7395:oregano
7367:Sichuan
7345:(RTX) (
7321:Protons
7284:(e.g.,
7217:Menthol
7199:incense
7119:Eugenol
7076:oregano
7016:Camphor
6984:Allicin
6974:Sichuan
6961:20-HETE
6951:13-HODE
6794:ML2-SA1
6695:tobacco
6646:AMG-333
6619:sucrose
6611:glucose
6609:(e.g.,
6592:(e.g.,
6558:Menthol
6492:Calcium
6308:tobacco
6284:AM-0902
6213:Sichuan
6154:tobacco
6043:Lindera
5920:mustard
5906:Allicin
5891:Sichuan
5868:4,5-EET
5830:channel
5708:5252711
5613:3615879
5562:2807614
5521:3839420
5472:3601443
5382:3012715
5359:Bibcode
5323:4280215
5300:Bibcode
5253:Bibcode
5206:Bibcode
5076:3516610
4863:6754178
4721:6884532
4648:7528853
4557:3932492
4360:2488260
4269:8274222
4225:3340178
4174:1459070
4082:2790762
4010:Bibcode
3974:3736709
3934:9039121
3884:2670635
3836:8258666
3792:4106241
3743:3567350
3694:3119152
3610:3684845
3507:3208155
3453:5091366
3334:1648091
3258:1525186
3145:9244739
3102:2501294
2974:7690778
2879:1327375
2870:1907511
2821:4617135
2686:9675028
2571:3791982
2522:4260681
2477:4694718
2414:4385421
2366:3248593
2310:3067055
2261:4575609
2194:Bibcode
2170:3481077
2044:3439529
2023:Bibcode
1993:5258044
1938:4292790
1882:4245146
1822:4575602
1769:9866708
1601:2962793
1254:Tag SNP
1082:nephron
1029:C57BL/6
1027:In the
686:12-HETE
637:opioids
575:epoxide
539:CYP4A22
522:CYP4A11
430:rodents
369:320.473
236:5283157
223:PubChem
155:4446281
7535:DHEA-S
7387:Thymol
7363:ginger
7286:4Ξ±-PDD
7149:ginger
6988:garlic
6970:ginger
6931:9-HODE
6828:ML-SI3
6789:ML-SA1
6784:MK6-83
6605:Sweet
6568:PMD 38
6548:Icilin
6401:DHEA-S
6293:celery
6209:ginger
6104:celery
6095:JT-010
6085:Icilin
6064:ginger
6027:celery
5932:wasabi
5924:radish
5910:garlic
5887:ginger
5785:
5750:
5742:
5706:
5698:
5663:
5655:
5620:
5610:
5569:
5559:
5528:
5518:
5479:
5469:
5435:
5427:
5389:
5379:
5330:
5320:
5271:
5224:
5180:
5172:
5126:
5118:
5083:
5073:
5031:
4995:
4987:
4951:
4916:
4861:
4853:
4811:
4767:
4759:
4719:
4711:
4691:
4646:
4638:
4599:
4564:
4554:
4512:
4471:
4430:
4422:
4367:
4357:
4318:
4298:
4267:
4232:
4222:
4181:
4171:
4134:959890
4132:
4124:
4089:
4079:
4040:
4030:
3981:
3971:
3932:
3891:
3881:
3842:
3834:
3799:
3789:
3750:
3740:
3701:
3691:
3652:
3617:
3607:
3568:
3560:
3514:
3504:
3460:
3450:
3413:434047
3411:
3403:
3368:
3332:
3291:
3256:
3220:
3179:
3143:
3135:
3100:
3059:
3013:
2972:
2965:288277
2962:
2923:
2877:
2867:
2828:
2818:
2766:
2725:
2684:
2648:
2613:
2578:
2568:
2529:
2519:
2475:
2467:
2421:
2411:
2373:
2363:
2317:
2307:
2268:
2258:
2212:
2168:
2160:
2122:
2086:
2051:
2041:
1991:
1983:
1945:
1935:
1889:
1879:
1829:
1819:
1767:
1732:
1690:
1652:
1608:
1598:
1559:
1448:Glioma
1392:Balb/c
1376:BT-474
1361:Cancer
1334:CYP4F2
1323:intron
1016:intima
678:5-HETE
619:, and
601:, and
567:CYP2J2
543:CYP2U1
535:CYP4Z1
530:CYP4F3
528:, and
526:CYP4F2
492:CYP4F8
488:CYP2U1
313:SMILES
197:C14748
33:Names
7525:DCDPC
7391:thyme
7127:clove
7123:basil
7080:thyme
6994:AM404
6921:2-APB
6807:SF-22
6779:EVP21
6763:TRPML
6661:DCDPC
6630:WS-12
6396:DCDPC
6247:onion
6124:thyme
6046:spp.)
6007:cumin
5938:AM404
5748:S2CID
5704:S2CID
5661:S2CID
5433:S2CID
5178:S2CID
5124:S2CID
4993:S2CID
4870:(PDF)
4859:S2CID
4831:(PDF)
4765:S2CID
4717:S2CID
4644:S2CID
4428:S2CID
4130:S2CID
4033:33189
3840:S2CID
3566:S2CID
3409:S2CID
3141:S2CID
2473:S2CID
2166:S2CID
1989:S2CID
1461:769-P
1457:786-O
1423:miRNA
1404:MCF-7
1196:TRPV1
1184:PPARΞ±
653:COX-2
645:Lasix
547:MCF-7
505:, 19(
284:InChI
126:ChEBI
104:JSmol
7530:DHEA
7475:BCTC
7369:and
7326:RhTx
7221:mint
7209:Low
7160:Heat
7094:DHEA
6976:and
6905:TRPV
6851:TRPP
6812:SN-2
6743:TPPO
6562:mint
6503:Cold
6487:BCTC
6466:TRPM
6446:Pyr3
6334:TRPC
6215:and
5893:and
5842:TRPA
5783:PMID
5740:PMID
5696:PMID
5653:PMID
5618:PMID
5567:PMID
5526:PMID
5477:PMID
5425:PMID
5387:PMID
5328:PMID
5269:PMID
5222:PMID
5170:PMID
5116:PMID
5081:PMID
5029:PMID
4985:PMID
4949:PMID
4914:PMID
4851:PMID
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