15-Hydroxyeicosatetraenoic acid

163: 2503:

pathways and enzymes that metabolize leukotriene A4 to its down-stream products. Preliminary studies have found that the eoxins have pro-inflammatory actions, suggest that they are involved in severe asthma, aspirin-induced asthma attacks, and perhaps other allergic reactions. The production of eoxins by Reed-Sternburg cells has also led to suggestion that they are involve in the lymphoma of Hodgkins disease. Drugs blocking the 15-lipoxygenases may be useful for inhibiting inflammation by reducing the production of the eoxins.

24: 2358:, adducting to, for example, the cysteines in transcription and transcription-related regulatory factors and enzymes to form their alkylated and thereby often inactivated products. It is presumed that the preceding activities of 15-oxo-ETE reflect its adduction to the indicated elements. 15-Oxo-ETE, at 2-10 μM, also inhibits the proliferation of cultured 2370:

cells and at the extremely high concentration of 100 μM inhibits the proliferation of cultured MBA-MD-231 and MCF7 breast cancer cells as well as SKOV3 ovarian cancer cells. They may use a similar "protein-adduction" mechanism; if so the target protein(s) for these effects have not been defined or

5479:

Kumar, K. A.; Arunasree, K. M.; Roy, K. R.; Reddy, N. P.; Aparna, A; Reddy, G. V.; Reddanna, P (2009). "Effects of (15S)-hydroperoxyeicosatetraenoic acid and (15S)-hydroxyeicosatetraenoic acid on the acute- lymphoblastic-leukaemia cell line Jurkat: Activation of the Fas-mediated death pathway".

2502:

viz, leukotriene A4; the latter metabolite is then converted to C4, D4, and E4 in succession. Formation of the eoxins is initiated by a 15-lipoxyenase-mediated metabolism of arachiconic acid to a 14,15-epoxide, eoxin A4 followed by its serial conversion to epoxins C4, D4, and E4 using the same

5279:

Shappell, S. B.; Gupta, R. A.; Manning, S; Whitehead, R; Boeglin, W. E.; Schneider, C; Case, T; Price, J; Jack, G. S.; Wheeler, T. M.; Matusik, R. J.; Brash, A. R.; Dubois, R. N. (2001). "15S-Hydroxyeicosatetraenoic acid activates peroxisome proliferator-activated receptor gamma and inhibits

2151:)-HpETE-forming enzymes and consequential fall in cellular 15-HETE production that occurs in human prostate cancer cells may be one mechanism by which this and perhaps other human cancer cells (e.g. those of the colon, rectum, and lung) avoid the apoptosis-inducing actions of 15( 6087:

O'Flaherty, J. T.; Rogers, L. C.; Paumi, C. M.; Hantgan, R. R.; Thomas, L. R.; Clay, C. E.; High, K; Chen, Y. Q.; Willingham, M. C.; Smitherman, P. K.; Kute, T. E.; Rao, A; Cramer, S. D.; Morrow, C. S. (2005). "5-Oxo-ETE analogs and the proliferation of cancer cells".

5391:

Chen, G. G.; Xu, H; Lee, J. F.; Subramaniam, M; Leung, K. L.; Wang, S. H.; Chan, U. P.; Spelsberg, T. C. (2003). "15-hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway".

542:

and perhaps other responses. Clinically, drugs that are stable analogs, and therefore mimic the anti-inflammatory actions of the lipoxins and drugs that block the production or actions of the pro-inflammatory eoxins may prove useful for treating acute and chronic

4219:

James A, Daham K, Backman L, Brunnström A, Tingvall T, Kumlin M, Edenius C, Dahlén SE, Dahlén B, Claesson HE (2013). "The influence of aspirin on release of eoxin C4, leukotriene C4 and 15-HETE, in eosinophilic granulocytes isolated from patients with asthma".

4789:

Ma, J; Zhang, L; Zhang, J; Liu, M; Wei, L; Shen, T; Ma, C; Wang, Y; Chen, Y; Zhu, D (2013). "15-lipoxygenase-1/15-hydroxyeicosatetraenoic acid promotes hepatocellular cancer cells growth through protein kinase B and heat shock protein 90 complex activation".

5196:

Wang, Y; Liang, D; Wang, S; Qiu, Z; Chu, X; Chen, S; Li, L; Nie, X; Zhang, R; Wang, Z; Zhu, D (2010). "Role of the G-protein and tyrosine kinase--Rho/ROK pathways in 15-hydroxyeicosatetraenoic acid induced pulmonary vasoconstriction in hypoxic rats".

3580:

Hammond, V. J.; Morgan, A. H.; Lauder, S; Thomas, C. P.; Brown, S; Freeman, B. A.; Lloyd, C. M.; Davies, J; Bush, A; Levonen, A. L.; Kansanen, E; Villacorta, L; Chen, Y. E.; Porter, N; Garcia-Diaz, Y. M.; Schopfer, F. J.; O'Donnell, V. B. (2012).

2045:)-HETE in cells, it is likely that the two metabolites share similar activities. In many studies, however, is not clear that these activities reflect their intrinsic action or reflect their conversion to the metabolites sited above. 2329:

which then moves to the nucleus, binds ARE, and induces production of, e.g. hemoxygenase-1, NADPH-quinone oxidoreductase, and possibly glutamate-cysteine ligase modifier. By these actions, 15-oxo-ETE may dampen inflammatory and/or

5235:

Naruhn, S; Meissner, W; Adhikary, T; Kaddatz, K; Klein, T; Watzer, B; Müller-Brüsselbach, S; Müller, R (2010). "15-hydroxyeicosatetraenoic acid is a preferential peroxisome proliferator-activated receptor beta/delta agonist".

3198:

Bylund, J; Kunz, T; Valmsen, K; Oliw, E. H. (1998). "Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes".

1502:-eicosatrienoic acid (i.e., 11,14,15-THETA) by a soluble epoxide hydrolase activity or, by acid in a non-enzymatic reaction (the R, S configuration of the hydroxy residues in the latter two metabolites has not been defined). 5643:

MacCarrone, M; Ranalli, M; Bellincampi, L; Salucci, M. L.; Sabatini, S; Melino, G; Finazzi-Agrò, A (2000). "Activation of different lipoxygenase isozymes induces apoptosis in human erythroleukemia and neuroblastoma cells".

1069:

The newly formed products formed by the pathways cited in the previous section are bioactive but may also flow into down-stream pathways to form other metabolites with a different sets of bioactivity. The initially formed

5572:

Tang, D. G.; Bhatia, B; Tang, S; Schneider-Broussard, R (2007). "15-lipoxygenase 2 (15-LOX2) is a functional tumor suppressor that regulates human prostate epithelial cell differentiation, senescence, and growth (size)".

8518: 8379: 8160: 7254: 7244: 1920:)-HETE, oxidized by NAD-dependent 5-hydroxyprostaglandin dehydrogenase to form 15-oxo-ETE which product can be converted its 13-cysteinyl-glycyl-glutamyl and then 13-cysteinyl-glycine products as described above for 5( 4316:

Lee, S. H.; Rangiah, K; Williams, M. V.; Wehr, A. Y.; Dubois, R. N.; Blair, I. A. (2007). "Cyclooxygenase-2-mediated metabolism of arachidonic acid to 15-oxo-eicosatetraenoic acid by rat intestinal epithelial cells".

2064:, i.e. BLT2. This receptor activation may mediate, at least in part, certain cell-stimulating activities of the two metabolites. BLT2 may be responsible in part or whole for mediating the growth-promoting and anti- 3915:

Kühn, H; Barnett, J; Grunberger, D; Baecker, P; Chow, J; Nguyen, B; Bursztyn-Pettegrew, H; Chan, H; Sigal, E (1993). "Overexpression, purification and characterization of human recombinant 15-lipoxygenase".

2371:

even suggested. This 15-oxo-ETE action may prove to inhibit the remodeling of blood vessels and reduce the growth of the cited cell types and cancers. At sub-micromolar concentrations, 15-oxo-ETE has weak

5136:

Pandey, V; Sultan, M; Kashofer, K; Ralser, M; Amstislavskiy, V; Starmann, J; Osprian, I; Grimm, C; Hache, H; Yaspo, M. L.; Sültmann, H; Trauner, M; Denk, H; Zatloukal, K; Lehrach, H; Wierling, C (2014).

7806: 7778: 7649: 4918:

Kiran Kumar, Y. V.; Raghunathan, A; Sailesh, S; Prasad, M; Vemuri, M. C.; Reddanna, P (1993). "Differential effects of 15-HPETE and 15-HETE on BHK-21 cell proliferation and macromolecular composition".

8495: 739:

enzymes. This release is stimulated or enhanced by cell stimulation. The freed arachidonic acid is then converted to 15-hydroperoxy/hydroxy products by one or more of the following five pathways.

3538:

Bergholte, J. M.; Soberman, R. J.; Hayes, R; Murphy, R. C.; Okita, R. T. (1987). "Oxidation of 15-hydroxyeicosatetraenoic acid and other hydroxy fatty acids by lung prostaglandin dehydrogenase".

5058:

Soumya, S. J.; Binu, S; Helen, A; Reddanna, P; Sudhakaran, P. R. (2013). "15(S)-HETE-induced angiogenesis in adipose tissue is mediated through activation of PI3K/Akt/mTOR signaling pathway".

5307:

Tang, S; Bhatia, B; Maldonado, C. J.; Yang, P; Newman, R. A.; Liu, J; Chandra, D; Traag, J; Klein, R. D.; Fischer, S. M.; Chopra, D; Shen, J; Zhau, H. E.; Chung, L. W.; Tang, D. G. (2002).

3061:

Serhan, C. N.; Takano, T; Maddox, J. F. (1999). "Aspirin-Triggered 15-Epi-Lipoxin A4 and Stable Analogs of Lipoxin A4 are Potent Inhibitors of Acute Inflammation: Receptors and Pathways".

3390:

Ochi, H; Morita, I; Murota, S (1992). "Roles of glutathione and glutathione peroxidase in the protection against endothelial cell injury induced by 15-hydroperoxyeicosatetraenoic acid".

6614: 3432:"Selective incorporation of (15S)-hydroxyeicosatetraenoic acid in phosphatidylinositol of human neutrophils: Agonist-induced deacylation and transformation of stored hydroxyeicosanoids" 2198:)-HETE inhibit angiogenesis and the growth of cultured human chronic myelogenous leukemia K-562 cells by a mechanism that is associated with the production of reactive oxygen species. 1714:)-HETE-containing-phospholipids may also be made directly by the action of 15-LO-1 on membrane phosphatidylinositols or phosphatidylethanolamines containing arachidonic acid at the 3632:

Alpert, S. E.; Walenga, R. W.; Mandal, A; Bourbon, N; Kester, M (1999). "15-HETE-substituted diglycerides selectively regulate PKC isotypes in human tracheal epithelial cells".

249:

InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

5093:

Li, J; Zhang, Y; Liu, Y; Shen, T; Zhang, H; Xing, Y; Zhu, D (2015). "PGC-1α plays a major role in the anti-apoptotic effect of 15-HETE in pulmonary artery endothelial cells".

4393:

Maskrey, B. H.; Bermúdez-Fajardo, A; Morgan, A. H.; Stewart-Jones, E; Dioszeghy, V; Taylor, G. W.; Baker, P. R.; Coles, B; Coffey, M. J.; Kühn, H; O'Donnell, V. B. (2007).

2910:

Sigal, E; Dicharry, S; Highland, E; Finkbeiner, W. E. (1992). "Cloning of human airway 15-lipoxygenase: Identity to the reticulocyte enzyme and expression in epithelium".

5348:

Kudryavtsev, I. A.; Golenko, O. D.; Gudkova, M. V.; Myasishcheva, N. V. (2002). "Arachidonic acid metabolism in growth control of A549 human lung adenocarcinoma cells".

4564:

Serhan, C. N. (1989). "On the relationship between leukotriene and lipoxin production by human neutrophils: Evidence for differential metabolism of 15-HETE and 5-HETE".

7018: 120: 5608:

Ochi, H; Morita, I; Murota, S (1992). "Mechanism for endothelial cell injury induced by 15-hydroperoxyeicosatetraenoic acid, an arachidonate lipoxygenase product".

3821:

Jubiz, W; Rådmark, O; Lindgren, J. A.; Malmsten, C; Samuelsson, B (1981). "Novel leukotrienes: Products formed by initial oxygenation of arachidonic acid at C-15".

5780:

Mahipal, S. V.; Subhashini, J; Reddy, M. C.; Reddy, M. M.; Anilkumar, K; Roy, K. R.; Reddy, G. V.; Reddanna, P (2007). "Effect of 15-lipoxygenase metabolites, 15-(

4754:

Cabral, M; Martín-Venegas, R; Moreno, J. J. (2013). "Role of arachidonic acid metabolites on the control of non-differentiated intestinal epithelial cell growth".

1378:

produced by ALOX15 rather than ALOX12, the enzyme responsible for making the various other hepoxilins in humans. The two novel hepoxilins are termed respectively

7969: 8500: 7905: 3583:"Novel keto-phospholipids are generated by monocytes and macrophages, detected in cystic fibrosis, and activate peroxisome proliferator-activated receptor-γ" 4434:

Thomas, C. P.; Morgan, L. T.; Maskrey, B. H.; Murphy, R. C.; Kühn, H; Hazen, S. L.; Goodall, A. H.; Hamali, H. A.; Collins, P. W.; O'Donnell, V. B. (2010).

7768: 7692: 396:)-HETE. Both of these metabolites, depending on the cell type which forms them, can be further metabolized to 15-oxo-eicosatetraenoic acid (15-oxo-ETE), 5( 1061:)-HETEs and other products. However, the uncontrolled overproduction of the 15-hydroperoxy products may react with other elements to produce cell injury. 459:)-HpETE. Both stereoisomers may also be formed as result of the metabolism of arachidonic acid by cellular microsomes or as a result of arachidonic acid 8698: 6271: 4525:"Formation of a novel dihydroxy acid from arachidonic acid by lipoxygenase-catalyzed double oxygenation in rat mononuclear cells and human leukocytes" 643:

at carbon positions 5, 8, 11, and 13 with Z indicating cis and E indicating trans isomerism. Both stereoisomers are produced from their corresponding

7259: 7122: 7096: 4488:

Serhan, C. N. (2005). "Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution".

4003: 8479: 8358: 8139: 5007:

Soumya, S. J.; Binu, S; Helen, A; Anil Kumar, K; Reddanna, P; Sudhakaran, P. R. (2012). "Effect of 15-lipoxygenase metabolites on angiogenesis: 15(

2120: 3012:"Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2" 8814: 8533: 7720: 2088:. These growth-stimulating effects could contribute to the progression of the cited cancer types in animal models or even humans and the excess 4436:"Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation" 3306:

Marshall, Paul J.; Kulmacz, Richard J. (1988). "Prostaglandin H synthase: Distinct binding sites for cyclooxygenase and peroxidase substrates".

8736: 8706: 8683: 8678: 8663: 8578: 8553: 7863: 7710: 7011: 3736:

Claesson, H. E. (2009). "On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma".

8673: 8618: 8583: 7843: 5986:"15-oxo-Eicosatetraenoic acid, a metabolite of macrophage 15-hydroxyprostaglandin dehydrogenase that inhibits endothelial cell proliferation" 4072:"Identification of 13-hydroxy-14,15-epoxyeicosatrienoic acid as an acid-stable endothelium-derived hyperpolarizing factor in rabbit arteries" 3124:-eicosatetraenoic acid synthesis within the cyclooxygenase active site of murine COX-2. Why acetylated COX-1 does not synthesize 15-(R)-hete" 8711: 8404: 7697: 7466: 7446: 7441: 7431: 7411: 7396: 7386: 7195: 7165: 7140: 265: 5828:"15-Oxoeicosatetraenoic acid is a 15-hydroxyprostaglandin dehydrogenase-derived electrophilic mediator of inflammatory signaling pathways" 4354:"Membrane translocation of 15-lipoxygenase in hematopoietic cells is calcium-dependent and activates the oxygenase activity of the enzyme" 2342:

but not other human lipoxygenases. This effect could also have anti-inflammatory and anti-oxidative effects by blocking the formation of

8819: 8643: 8638: 8633: 8434: 8424: 8263: 8258: 8195: 7873: 7816: 7471: 7406: 7401: 7391: 7290: 7285: 7280: 7205: 7185: 7160: 7150: 7145: 7135: 7130: 7112: 3674:"Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells" 2321:) while concurrently activating anti-oxidant responses upregulated through the anti-oxidant response element (ARE) by forcing cytosolic 8469: 8464: 8333: 8123: 7730: 7654: 7544: 7539: 7456: 7426: 7381: 7376: 7371: 7190: 7180: 7175: 7170: 8829: 8809: 8789: 8784: 8608: 8343: 8240: 8114: 7868: 7639: 7481: 7451: 7200: 7004: 6172:

O'Flaherty, J. T.; Kuroki, M; Nixon, A. B.; Wijkander, J; Yee, E; Lee, S. L.; Smitherman, P. K.; Wykle, R. L.; Daniel, L. W. (1996).

5731:"15-LOX metabolites and angiogenesis: Angiostatic effect of 15(S)-HPETE involves induction of apoptosis in adipose endothelial cells" 2072:)-HETE in cultured human breast cancer cells; human cancer colon cells, human hepatocellular HepG2 and SMMC7721 cancer cells; mouse 8804: 8794: 8726: 8658: 8459: 8080: 7853: 7801: 7763: 7735: 7634: 7624: 7416: 6266: 2456: 4692:

O'Flaherty, J. T.; Wooten, R. E.; Samuel, M. P.; Thomas, M. J.; Levine, E. A.; Case, L. D.; Akman, S. A.; Edwards, I. J. (2013).

3672:

Feltenmark, S; Gautam, N; Brunnström, A; Griffiths, W; Backman, L; Edenius, C; Lindbom, L; Björkholm, M; Claesson, H. E. (2008).

3227: 2432: 2363: 2174:)-HETE, particularly when induced by high concentrations (e.g. >1-10 micromolar), may be due to a less specific mechanism: 15( 526:)-HpETE, and many of their derivative metabolites are thought to have physiologically important functions. They appear to act as 2539: 2537: 440:)-HpETE, in addition to having intrinsic biological activities, are key precursors to numerous biologically active derivatives. 6557: 2459:, i.e. they potently inhibit the progression and contribute to the resolution of diverse inflammatory and allergic reactions. 6298: 3774:

Sachs-Olsen, C; Sanak, M; Lang, A. M.; Gielicz, A; Mowinckel, P; Lødrup Carlsen, K. C.; Carlsen, K. H.; Szczeklik, A (2010).

3078: 2534: 2359: 1648: 958: 954: 181: 5788:)-HETE on chronic myelogenous leukemia cell line K-562: Reactive oxygen species (ROS) mediate caspase-dependent apoptosis". 2871:"Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid by human umbilical vein endothelial cells" 2522: 1675:)-eicosatrienoic acid; the latter metabolite is attacked by γ-glutamyl-transferase to form 13-cysteinyl-glycine,15-oxo-5( 1098: 421: 8505: 2544:

Moreno, J. J. (2009). "New aspects of the role of hydroxyeicosatetraenoic acids in cell growth and cancer development".

1718:-2 positions. The phosphatidylethanolamine-bound 15-HETE may be converted to phosphatidylethanolamine-bound 15-oxo-ETE. 6125:"Stimulating properties of 5-oxo-eicosanoids for human monocytes: Synergism with monocyte chemotactic protein-1 and -3" 3163:

Oliw, E. H. (1993). "Bis-Allylic hydroxylation of linoleic acid and arachidonic acid by human hepatic monooxygenases".

3343:"Reaction mechanisms of 15-hydroperoxyeicosatetraenoic acid catalyzed by human prostacyclin and thromboxane synthases" 5309:"Evidence that arachidonate 15-lipoxygenase 2 is a negative cell cycle regulator in normal prostate epithelial cells" 240: 8092: 1478:-eicosatrienoic acid (i.e., 15-H-11,12-EETA) by a hydroperoxide isomerase activity and then to 11,12,15-trihydroxy-5 8048: 7554: 7491: 7318: 7239: 6520: 5435:

Chang, M. S.; Schneider, C; Roberts, R. L.; Shappell, S. B.; Haselton, F. R.; Boeglin, W. E.; Brash, A. R. (2005).

2104:)-HETE may also act through BLT2 to stimulate an immediate contractile response in rat pulmonary arteries and its 1896:)-HpETE, subject to decomposition to form various bifuctional potentially toxic electrophiles such as 4-hydroxy-2( 337: 7234: 7091: 5525:"15-lipoxygenase-2 (15-LOX-2) is expressed in benign prostatic epithelium and reduced in prostate adenocarcinoma" 834: 7888: 1075: 8513: 8374: 8155: 7304: 7249: 1858: 924: 8107: 2436: 928: 4830:"Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth" 2744:

Leeper KV (1993). "Diagnosis and treatment of pulmonary infections in adult respiratory distress syndrome".

2498:. Formation of the leukotrienes is initiated by 5-lipoxygenase metabolism of arachidonic acid to form a 5,6- 1300:

and presumed to be conducted by the same enzymes (Eoxins are also termed 14,15-leukotrienes or 14,15-LTs).

1272:. These metabolic transformations are similar to those in the pathway that metabolizes arachidonic acid to 8910: 8774: 8073: 7788: 7750: 217: 158: 8764: 7611: 2440: 1862: 1601:

derivative, eoxin A4, and further metabolized to eoxin C4, eoxin D4, and eoxin E4 (there is no eoxin B4).

5681:"Arachidonic acid-induced apoptosis in rat hepatoma AS-30D cells is mediated by reactive oxygen species" 2412: 2253:)-HETE binds with and activates peroxisome proliferator-activated receptor gamma. The precursor of 15( 2057: 8033: 4687: 4685: 2229:

in mammalian cells and thereby may contripute to the development and/or progression of human cancers.

487:

stereoisomers are sometimes referred to as 15-HpETE and 15-HETE, proper usage should identify them as

8449: 8323: 7215: 7072: 6291: 2061: 392:

product is extremely short-lived in cells: if not otherwise metabolized, it is rapidly reduced to 15(

3102:

Rowlinson, S. W.; Crews, B. C.; Goodwin, D. C.; Schneider, C; Gierse, J. K.; Marnett, L. J. (2000).

1074:)-HpETE may be further metabolized by its parent cell or pass it to nearby cell by a process termed 8100: 7979: 7947: 7826: 6174:"5-Oxo-eicosatetraenoate is a broadly active, eosinophil-selective stimulus for human granulocytes" 5139:"Comparative analysis and modeling of the severity of steatohepatitis in DDC-treated mouse strains" 4963:)-hydroxyeicosatetraenoic acid induces angiogenesis via activation of PI3K-Akt-mTOR-S6K1 signaling" 4682: 4395:"Activated platelets and monocytes generate four hydroxyphosphatidylethanolamines via lipoxygenase" 2687:"Role of 15-lipoxygenase/15-hydroxyeicosatetraenoic acid in hypoxia-induced pulmonary hypertension" 2408: 2081: 1699: 1137: 1128: 981:, however, COX-1 is inactive while COX-2 attacks arachidonic acid to produce almost exclusively 15( 2163:)-HETE and one of its forming enzymes, particularly 15-LOX-2, appear to act as tumor suppressors. 7915: 7725: 7058: 7041: 6123:

Sozzani, S; Zhou, D; Locati, M; Bernasconi, S; Luini, W; Mantovani, A; O'Flaherty, J. T. (1996).

2183: 1245: 636: 8688: 8298: 8293: 8205: 2093: 1528:-eicosatrienoic acid (i.e., 15-H-11,12-EETA) by a hydroperoxide isomerase activity, possibly a 1110: 588: 5826:

Snyder, N. W.; Golin-Bisello, F; Gao, Y; Blair, I. A.; Freeman, B. A.; Wendell, S. G. (2015).

8942: 8283: 7047: 6979: 6773: 6671: 6426: 3997: 2384: 1931:)-HETE, oxygenated by ALOX5 to form its 5,6-oxido derivative which then rearranges to the 15( 1102: 592: 140: 4483: 4481: 3010:

Mulugeta, S; Suzuki, T; Hernandez, N. T.; Griesser, M; Boeglin, W. E.; Schneider, C (2010).

2773:"A lipoxygenase in rabbit reticulocytes which attacks phospholipids and intact mitochondria" 8937: 8932: 8170: 8028: 7674: 6284: 5839: 5150: 4705: 3869: 3685: 3494:"Substitution of 15-hydroxyeicosatetraenoic acid in the phosphoinositide signaling pathway" 3443: 2961: 2784: 1695: 1506: 1320: 1124: 1106: 226: 96: 36: 5952: 5888:"Inhibitory and mechanistic investigations of oxo-lipids with human lipoxygenase isozymes" 3956:"Pharmaceutical policies in European countries in response to the global financial crisis" 162: 8: 8947: 6716: 5586: 4478: 3749: 2097: 535: 531: 86: 5843: 5154: 4709: 4650:"Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2" 3873: 3689: 3447: 2965: 2788: 2713: 2686: 8131: 7033: 6246: 6203: 6154: 6061: 6034: 6010: 5985: 5961: 5936: 5912: 5887: 5860: 5827: 5757: 5730: 5549: 5524: 5505: 5417: 5373: 5261: 5173: 5138: 5118: 5040: 4900: 4728: 4693: 4625: 4600: 4462: 4435: 4245: 4201: 4147: 4122: 4098: 4071: 4043: 4018: 3980: 3955: 3803: 3708: 3673: 3609: 3582: 3367: 3342: 3283: 3266: 3038: 3011: 2810: 2726: 2662: 2637: 2608: 2583: 2306: 1319:)-dihydroxy-5,9,11,13-eicosatetraenoic acid (8,15-leukotrienes B4) and to two isomeric 5540: 4541: 4524: 4019:"Role of arachidonic acid lipoxygenase metabolites in the regulation of vascular tone" 3892: 3857: 3510: 3493: 2887: 2870: 2846: 2829: 8278: 8122: 7682: 6238: 6195: 6146: 6105: 6066: 6015: 5966: 5917: 5865: 5805: 5762: 5702: 5661: 5625: 5621: 5590: 5554: 5497: 5458: 5409: 5365: 5330: 5289: 5253: 5214: 5178: 5110: 5075: 5032: 4984: 4936: 4932: 4892: 4851: 4807: 4771: 4733: 4671: 4630: 4581: 4577: 4546: 4505: 4467: 4416: 4375: 4334: 4295: 4237: 4193: 4188: 4171: 4152: 4103: 4048: 3985: 3933: 3929: 3897: 3838: 3834: 3795: 3753: 3713: 3649: 3614: 3555: 3551: 3515: 3471: 3466: 3431: 3407: 3403: 3372: 3323: 3319: 3288: 3247: 3243: 3208: 3180: 3176: 3145: 3084: 3074: 3043: 2989: 2984: 2949: 2927: 2892: 2851: 2802: 2797: 2772: 2753: 2718: 2667: 2638:"Proresolving lipid mediators and mechanisms in the resolution of acute inflammation" 2613: 2561: 2367: 1857:)-hydroxy-ETE). The latter two metabolites may also be made by 15-LO's metabolism of 1049:-eicosatetraenoic acids. This non-enzymatic reaction is promoted in cells undergoing 6250: 6207: 6158: 5509: 5421: 5377: 5265: 5122: 4249: 3645: 2923: 2814: 432:, and other products that have less well-defined activities and functions. Thus, 15( 206: 8528: 8384: 8175: 8043: 7600: 6996: 6970: 6950: 6930: 6922: 6873: 6806: 6767: 6722: 6415: 6404: 6382: 6356: 6321: 6230: 6185: 6136: 6097: 6056: 6046: 6005: 5997: 5956: 5948: 5907: 5899: 5855: 5847: 5797: 5752: 5742: 5692: 5653: 5617: 5582: 5544: 5536: 5489: 5448: 5401: 5357: 5320: 5245: 5206: 5168: 5158: 5102: 5067: 5044: 5024: 4974: 4928: 4882: 4841: 4799: 4763: 4723: 4713: 4661: 4620: 4612: 4573: 4536: 4497: 4457: 4447: 4406: 4365: 4326: 4285: 4229: 4205: 4183: 4142: 4134: 4093: 4083: 4038: 4030: 3975: 3967: 3925: 3887: 3877: 3830: 3807: 3787: 3745: 3703: 3693: 3641: 3604: 3594: 3547: 3505: 3461: 3451: 3399: 3362: 3354: 3315: 3278: 3239: 3172: 3135: 3066: 3033: 3023: 2979: 2969: 2919: 2882: 2841: 2792: 2730: 2708: 2698: 2657: 2649: 2603: 2595: 2553: 2380: 2331: 2085: 1609: 1050: 708: 596: 377: 288: 6234: 4979: 4958: 4904: 4871:"15-LO/15-HETE mediated vascular adventitia fibrosis via p38 MAPK-dependent TGF-β" 4616: 3492:

Legrand, A. B.; Lawson, J. A.; Meyrick, B. O.; Blair, I. A.; Oates, J. A. (1991).

3065:. Advances in Experimental Medicine and Biology. Vol. 447. pp. 133–149. 1268:

which is in turn further metabolized by removal of the glycine residue to form EXE

923:

rather than arachidonic acid. It therefore forms linoleic acid metabolites (e.g.

6395: 6141: 6124: 6101: 5437:"Detection and subcellular localization of two 15S-lipoxygenases in human cornea" 5163: 4803: 4767: 4718: 3775: 3228:"Preparation and characterization of hydroperoxy-eicosatetraenoic acids (HPETEs)" 3070: 2653: 2339: 1655:)-HETE, may be acylated into membrane phosphatidylethanolamine or, similar to 15( 1617: 1536: 1529: 1303:

Metabolized alternatively by 15-LO-1 to various 8,15-diHETEs including the two 8(

1162: 1054: 1000: 996: 732: 448: 5937:"Redox-dependent anti-inflammatory signaling actions of unsaturated fatty acids" 4501: 4034: 845:)-HETE), respectively, or further metabolized through other enzyme pathways; 14( 503:

stereoisomers but can be further metabolized to bioactive products viz., the 15(

8250: 8053: 7573: 7526: 7518: 7510: 7353: 7345: 7337: 7267: 7104: 7030: 6907: 6899: 6858: 6838: 6830: 6822: 6789: 6781: 6754: 6746: 6738: 6730: 6581: 6573: 6565: 6544: 6536: 6487: 6479: 6190: 6173: 6035:"Cellular uptake and antiproliferative effects of 11-oxo-eicosatetraenoic acid" 5523:

Shappell, S. B.; Boeglin, W. E.; Olson, S. J.; Kasper, S; Brash, A. R. (1999).

5106: 4846: 4829: 4352:

Brinckmann, R; Schnurr, K; Heydeck, D; Rosenbach, T; Kolde, G; Kühn, H (1998).

4123:"Human CYP2S1 metabolizes cyclooxygenase- and lipoxygenase-derived eicosanoids" 3862:

Proceedings of the National Academy of Sciences of the United States of America

3791: 3436:

Proceedings of the National Academy of Sciences of the United States of America

2954:

Proceedings of the National Academy of Sciences of the United States of America

2495: 2491: 2487: 2483: 2294: 1294: 1287: 1280: 1273: 1153:)-HETE-bound phospholipoid analogs. Phosphatidylinositol phospholipids with 15( 460: 331: 6221:

Sadeghian H, Jabbari A (2016). "15-Lipoxygenase inhibitors: a patent review".

5903: 5851: 5801: 5361: 5028: 3358: 2703: 2599: 2557: 2415:, to activate its various target cells. As such, it is a potent stimulator of 2285:)-decanal and therefore be involved in cancer development and/or progression. 1323:-14,15-dihydroxy-5-cis-8,10,12-eicosatetraenoic acids (14,15-leukotrienes B4). 8926: 8888: 8878: 8741: 8721: 8716: 8668: 8648: 8444: 8313: 8268: 8023: 6340: 4067: 2577: 2575: 2314: 1644: 1142: 962: 920: 480: 151: 4452: 4121:

Bui, P; Imaizumi, S; Beedanagari, S. R.; Reddy, S. T.; Hankinson, O (2011).

4088: 3769: 3767: 3698: 3599: 3456: 2974: 1663:

to form a 13-cysteinyl-glycyl-glutamine adduct viz., 13-glutatione,15-oxo-5(

8853: 8848: 8756: 8751: 8731: 8693: 8653: 8628: 8623: 8573: 8429: 8328: 8318: 8308: 8303: 8273: 8245: 7858: 7644: 6881: 6814: 6800: 6447: 6242: 6109: 6070: 6019: 6001: 5970: 5921: 5869: 5809: 5766: 5706: 5697: 5680: 5665: 5657: 5594: 5558: 5501: 5462: 5413: 5369: 5334: 5325: 5308: 5293: 5257: 5249: 5218: 5182: 5114: 5079: 5036: 4988: 4896: 4855: 4811: 4775: 4737: 4675: 4666: 4649: 4634: 4509: 4471: 4420: 4411: 4394: 4370: 4353: 4338: 4299: 4290: 4273: 4241: 4197: 4156: 4138: 4107: 4052: 3989: 3882: 3799: 3757: 3717: 3667: 3665: 3663: 3653: 3618: 3376: 3149: 3140: 3103: 3088: 3047: 2722: 2671: 2617: 2565: 2351: 2105: 1936: 1725:) to form its 5,6-trans epoxide derivative which may then rearrange to the 1691: 1605: 1312: 1120: 1022: 745:: Cells metabolize arachidonic acid with 15-lipoxygenase-1 (i.e., 15-LO-1, 728: 544: 539: 6199: 6150: 6090:

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids

5629: 5071: 4940: 4585: 4550: 4392: 4379: 3971: 3937: 3901: 3842: 3559: 3519: 3475: 3411: 3327: 3292: 3251: 3212: 3184: 2993: 2931: 2896: 2855: 2757: 2572: 8883: 8873: 8863: 8746: 8598: 8588: 8563: 8558: 8548: 8543: 8523: 8399: 8389: 8288: 8235: 8225: 8215: 8185: 8180: 8165: 8038: 7687: 7476: 7421: 7027: 6699: 6504: 6470: 5729:

Soumya, S. J.; Binu, S; Helen, A; Reddanna, P; Sudhakaran, P. R. (2014).

5453: 5436: 3764: 2512: 2355: 1660: 1264:

is further metabolized by removal of the γ-L-glutamyl residue to form EXD

1253: 1166: 640: 512: 8480: 8359: 8140: 6051: 5210: 3660: 3028: 2334:

responses. In a cell-free system, 15-oxo-ETE is a moderately potent (IC

939:)-HETE. 15-LOX-2 also differs from 15-LOX-1 in that it does not make 12( 8893: 8868: 8858: 8439: 8209: 8190: 7995: 7932: 7669: 7461: 7436: 6963: 6331: 6307: 5493: 4267: 4265: 4263: 4261: 4259: 3575: 3573: 3571: 3569: 2806: 2424: 2420: 2372: 2139:

cell lines and non-malignant human prostate cells; lung adenocarcinoma

2077: 1647:

of the A, E, and F series to their 15-keto analogs viz., NAD-dependent

1094: 604: 373: 316: 171: 131: 7711: 6033:

Snyder, N. W.; Revello, S. D.; Liu, X; Zhang, S; Blair, I. A. (2013).

5747: 5405: 4887: 4870: 4330: 4233: 3267:"Neutrophil-aggregating activity of monohydroxyeicosatetraenoic acids" 2186:. These species trigger cells to activate their death programs, i.e. 8613: 8603: 8538: 8419: 8409: 8230: 7848: 7773: 7664: 7629: 6892: 5347: 4065: 3487: 3485: 2416: 2347: 2187: 2140: 2073: 2065: 1567: 1559: 1375: 4256: 3858:"A second pathway of leukotriene biosynthesis in porcine leukocytes" 3566: 2869:

Hopkins, N. K.; Oglesby, T. D.; Bundy, G. L.; Gorman, R. R. (1984).

1490:-eicosatrienoic acid (i.e. 11,12,15-THETA) and 11,14,15-trihydroxy-5 330:

Except where otherwise noted, data are given for materials in their

8593: 8568: 8394: 8220: 8200: 8000: 7964: 7878: 7811: 7702: 7659: 7366: 7155: 6851: 6654: 6646: 6638: 6630: 5642: 5230: 5228: 4917: 3953: 3671: 2479: 2475: 2471: 2467: 2376: 2092:

that causes the narrowing of pulmonary arteries in hypoxia-induced

2089: 1636: 1116: 444: 389: 8124: 6171: 5881: 5879: 3482: 2447:

and thereby can stimulate or inhibit cells independently of OXE1.

2444: 2302: 119: 8779: 8414: 6690: 6683: 6679: 5934: 5571: 5002: 5000: 4998: 4921:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

4566:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

4351: 4272:

Lee, S. H.; Williams, M. V.; Dubois, R. N.; Blair, I. A. (2005).

4066:

Chawengsub, Y; Gauthier, K. M.; Nithipatikom, K; Hammock, B. D.;

3918:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

3165:

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism

3005: 3003: 2499: 2343: 2226: 2108:

effect on human umbilical and dermal vascular endothelial cells.

1726: 1598: 978: 908: 559:)-HETE is unambiguously designated by a shortened version of its 527: 508: 425: 193: 6086: 5225: 4691: 2310: 2159:)-HETE and thereby proliferate and spread. In this scenario, 15( 8348: 7937: 7740: 7594: 5935:

Delmastro-Greenwood, M; Freeman, B. A.; Wendell, S. G. (2014).

5876: 4694:"Fatty acid metabolites in rapidly proliferating breast cancer" 4601:"The eosinophil chemoattractant 5-oxo-ETE and the OXE receptor" 3009: 2909: 2404: 2326: 2144: 2143:; human colorectal cancer cells; corneal epithelial cells; and 2127:)-HETE to inhibit the growth of cultured human prostate cancer 1640: 1563: 1552: 1548: 1544: 1540: 1459: 746: 736: 6276: 4995: 4869:

Zhang, L; Li, Y; Chen, M; Su, X; Yi, D; Lu, P; Zhu, D (2014).

4648:

Yokomizo, T; Kato, K; Hagiya, H; Izumi, T; Shimizu, T (2001).

3954:

Vogler, S; Zimmermann, N; Leopold, C; De Joncheere, K (2011).

3264: 3101: 3000: 919:)-HETE. However this enzyme has a preference for metabolizing 6943: 6598: 5610:

Biochimica et Biophysica Acta (BBA) - Molecular Cell Research

5434: 5278: 5234: 4823: 4821: 2517: 2322: 2136: 2132: 1722: 1396:

can be further metabolized by glutathione transferases to 11(

1201: 969:)-HETE and a racemic mixture of 15-HETEs composed of ~22% 15( 560: 429: 109: 23: 5886:

Armstrong, M. M.; Diaz, G; Kenyon, V; Holman, T. R. (2014).

4792:

The International Journal of Biochemistry & Cell Biology

4756:

The International Journal of Biochemistry & Cell Biology

3914: 3820: 3537: 2770: 2201:

Several bifunctional electrophilic breakdown products of 15(

6122: 5825: 5779: 4218: 4120: 3773: 2771:

Schewe, T; Halangk, W; Hiebsch, C; Rapoport, S. M. (1975).

2428: 2318: 2298: 2128: 5522: 5135: 4818: 4753: 4170:

Brash, A. R.; Yu, Z; Boeglin, W. E.; Schneider, C (2007).

4016: 3631: 2827: 2350:. 15-Oxo-ETE is an example of an α,β unsaturated ketone 2265:)-HpETE, break down to the mutagenic products 4-hydroxy-2( 2041:)-HpETE. Since this precursor is rapidly converted to 15( 5885: 5006: 4523:

Maas, R. L.; Turk, J; Oates, J. A.; Brash, A. R. (1982).

4433: 3579: 3491: 3201:

The Journal of Pharmacology and Experimental Therapeutics

2868: 8485:

Tooltip Peroxisome proliferator-activated receptor gamma

8364:

Tooltip Peroxisome proliferator-activated receptor delta

8145:

Tooltip Peroxisome proliferator-activated receptor alpha

7555: 7492: 7319: 4017:

Chawengsub, Y; Gauthier, K. M.; Campbell, W. B. (2009).

3776:"Eoxins: A new inflammatory pathway in childhood asthma" 1562:

by epidermis-type lipoxygenase 3 (eLOX3, encoded by the

6082: 6080: 5728: 5306: 5057: 4749: 4747: 4647: 4169: 3949: 3947: 3226:

Boeynaems, J. M.; Oates, J. A.; Hubbard, W. C. (1980).

2147:

T-cell leukemia cells. The decline in the level of 15(

2123:. This activation may contribute to the ability of 15( 380:. Various cell types metabolize arachidonic acid to 15( 7716:

Tooltip Arachidonate 5-lipoxygenase-activating protein

7305: 5478: 4490:

Prostaglandins, Leukotrienes and Essential Fatty Acids

4315: 4271: 907:: Cells also used 15-lipoxygenase 2 (i.e. 15-LOX-2 or 6032: 3265:

O'Flaherty JT, Thomas MJ, Lees CJ, McCall CE (1981).

3225: 3197: 2636:

Buckley, C. D.; Gilroy, D. W.; Serhan, C. N. (2014).

1643:

analog, 15-oxo-ETE, by the same enzyme that converts

873:

is metabolized by 15-LO-1 to various isomers of 8,15(

499:)-HETE lack some of the activity attributed to their 7889: 7789: 7751: 7026: 6077: 5390: 4744: 3944: 2037:)-HETE but not that of its less stable precursor 15( 1604:

Degraded non-enzymatically to various cell-injuring

1374:)-eicosatrienoic acid; these two products are novel 1256:(i.e. γ-L-glutamyl-L-cysteinylglycine) bound in the 961:(COX-2) to metabolize arachidonic acid primarily to 7612: 5646:

Biochemical and Biophysical Research Communications

3823:

Biochemical and Biophysical Research Communications

2948:Brash, A. R.; Boeglin, W. E.; Chang, M. S. (1997). 2635: 180: 8129:Tooltip Peroxisome proliferator-activated receptor 5984:Wei, C; Zhu, P; Shah, S. J.; Blair, I. A. (2009). 4522: 3060: 2950:"Discovery of a second 15S-lipoxygenase in humans" 1057:of 15-hydroperoxy products may convert then to 15( 8765: 7216: 7073: 5678: 4311: 4309: 2947: 999:, e.g. CYP2C19, metabolize arachidonic acid to a 727:-eicosatetraenoic acid) from its storage site in 550: 8924: 7980: 7948: 7827: 6220: 5607: 5441:Investigative Ophthalmology & Visual Science 5280:proliferation in PC3 prostate carcinoma cells". 5195: 3856:Maas, R. L.; Brash, A. R.; Oates, J. A. (1981). 3389: 2423:, as well as other OXE1-bearing cells including 2121:peroxisome proliferator-activated receptor gamma 1021:: The spontaneous and non-enzymatically induced 483:residue in opposite orientations. While the two 205: 7916: 7059: 5983: 4788: 3678:Proceedings of the National Academy of Sciences 3429: 3305: 2830:"Metabolism of leukotriene D by porcine kidney" 95: 5092: 4306: 3855: 2581: 8108: 7012: 6292: 5821: 5819: 4868: 4002:: CS1 maint: DOI inactive as of April 2024 ( 3533: 3531: 3529: 3425: 3423: 3421: 3341:Yeh, H. C.; Tsai, A. L.; Wang, L. H. (2007). 2943: 2941: 2584:"Cyclooxygenases and lipoxygenases in cancer" 2297:, 15-oxo-ETE inactivates IKKβ (also known as 2020: 428:, a class of pro-inflammatory mediators, the 6214: 4827: 4598: 4212: 4070:; Narsimhaswamy, D; Campbell, W. B. (2009). 2190:, and/or are openly toxic to the cells. 15( 2119:)-HETE also directly bind with and activate 2033:Most studies have analyzed the action of 15( 985:)-HETE along with its presumed precursor 15( 929:9-hydroperoxy/hydroxyl-octadecadienoic acids 801:-14,15-leukotriene A4 as minor products; 15( 583:-eicosatetraenoic acid. In this terminology 4956: 4172:"The hepoxilin connection in the epidermis" 3731: 3729: 3727: 3340: 2305:-mediated pro-inflammatory responses (e.g. 2080:cell line); rat PA adventitia fibroblasts; 61:)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid 8115: 8101: 8049:5-HPETE (arachidonic acid 5-hydroperoxide) 7019: 7005: 6299: 6285: 5816: 5575:Prostaglandins & Other Lipid Mediators 5474: 5472: 4952: 4950: 3780:Journal of Allergy and Clinical Immunology 3738:Prostaglandins & Other Lipid Mediators 3526: 3418: 2938: 2737: 2403:)-hydroxy-ETE is properly a member of the 2390: 2354:. These ketones are highly reactive with 1881:)-HETE by the same pathway that reduces 5( 1833:)-diHETE may then be oxidized to 5-oxo-15( 1428:) which is then further metabolized to 11( 479:stereoisomers differ only in having their 161: 139: 6189: 6140: 6060: 6050: 6009: 5960: 5911: 5859: 5756: 5746: 5696: 5548: 5452: 5324: 5172: 5162: 5095:Respiratory Physiology & Neurobiology 4978: 4886: 4845: 4727: 4717: 4665: 4624: 4540: 4461: 4451: 4410: 4369: 4289: 4187: 4146: 4097: 4087: 4042: 3979: 3891: 3881: 3707: 3697: 3608: 3598: 3509: 3465: 3455: 3366: 3282: 3139: 3037: 3027: 2983: 2973: 2886: 2845: 2796: 2712: 2702: 2661: 2631: 2629: 2627: 2607: 416:)-hydroxyeicosatetraenoic acid (5-oxo-15( 225: 7563:Tooltip Cysteinyl leukotriene receptor E 7500:Tooltip Cysteinyl leukotriene receptor 2 7327:Tooltip Cysteinyl leukotriene receptor 1 3735: 3724: 3430:Brezinski, M. E.; Serhan, C. N. (1990). 2068:(i.e. anti-cell death) activities of 15( 1702:. Phospholipid products contain this 15( 1594:-eicosatetraenoic acid) and 15-oxo-ETE). 1141:-2 position of these phospholipids (see 5469: 4947: 3540:Archives of Biochemistry and Biophysics 3392:Archives of Biochemistry and Biophysics 3347:Archives of Biochemistry and Biophysics 3308:Archives of Biochemistry and Biophysics 2096:or narrowing of portal arteries in the 1097:reactions including those possessed by 957:(i.e. cyclooxygenenase-1 or COX-1) and 925:13-hydoxyperoxy/hydroxy-octadecadienoic 538:agents that are involved in regulating 384:)-hydroperoxyeicosatetraenoic acid (15( 8925: 7310:Tooltip Cysteinyl leukotriene receptor 5482:Biotechnology and Applied Biochemistry 4563: 4487: 4274:"Cyclooxygenase-2-mediated DNA damage" 2743: 2684: 2624: 2543: 2407:family of agonists which binds to the 2360:human umbilical vein endothelial cells 1979:-eicosatetraenoic acid) and 15-epi-LXB 273:CCCCC(/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O 152: 8096: 7000: 6280: 6223:Expert Opinion on Therapeutic Patents 5953:10.1146/annurev-physiol-021113-170341 4957:Zhang, B; Cao, H; Rao, G. N. (2005). 4023:AJP: Heart and Circulatory Physiology 2691:The Journal of Physiological Sciences 2455:LXA4, LXB4, AT-LXA4, and AT-LXB4 are 2166:Some of the inhibitory effects of 15( 2011:-eicosatetraenoic acid, respectively. 1649:15-hydroxyprostaglandin dehydrogenase 1184:-epoxide, 14,15-trans-epoxide-oxido-5 1064: 959:prostaglandin-endoperoxide synthase 2 955:prostaglandin-endoperoxide synthase 1 471:)-HpETE may be rapidly reduced to 15( 447:) metabolize arachidonic acid to the 404:)-dihydroxy-eicosatetraenoic acid (5( 252:Key: JSFATNQSLKRBCI-VAEKSGALSA-N 7898:Tooltip Leukotriene B4 ω-hydroxylase 7794:Tooltip Arachidonate 15-lipoxygenase 7756:Tooltip Arachidonate 12-lipoxygenase 5892:Bioorganic & Medicinal Chemistry 5587:10.1016/j.prostaglandins.2006.05.022 3750:10.1016/j.prostaglandins.2008.12.003 3162: 2443:). It also binds with and activates 2249:)-HETE and with similar potency, 15( 1236:-eicosatetraenoic acid (i.e. eoxin C 1180:Metabolized by 15-LO-1 to its 14,15- 1011:)-HETEs, >90% of which is the 15( 809:)-HpETE are rapidly converted to 15( 7617:Tooltip Arachidonate 5-lipoxygenase 4529:The Journal of Biological Chemistry 3498:The Journal of Biological Chemistry 3128:The Journal of Biological Chemistry 3063:Lipoxygenases and their Metabolites 2875:The Journal of Biological Chemistry 2828:Bernström K, Hammarström S (1981). 2523:Specialized pro-resolving mediators 2293:In cultured human monocytes of the 1853:-eicosatetraenoate (i.e., 5-oxo-15( 1099:prostaglandin-endoperoxide synthase 893:-eicosatetraenoic acids, e.g. 8,15( 422:specialized pro-resolving mediators 196: 13: 5679:Dymkowska, D; Wojtczak, L (2009). 3634:The American Journal of Physiology 2912:The American Journal of Physiology 2457:specialized proresolving mediators 2178:)-HpETE and to a lesser extent 15( 2100:accompanying liver cirrhosis. 15( 1135:)-HpETE is bound primarily at the 753:)-HpETE as a major product and 12( 14: 8959: 8770:Tooltip Selective PPARγ modulator 8029:γ-Linolenic acid (gamolenic acid) 7683:Meclofenamic acid (meclofenamate) 7224:Tooltip Leukotriene B4 receptor 2 7081:Tooltip Leukotriene B4 receptor 1 6615:Arachidonic acid 15-hydroperoxide 6260: 5529:The American Journal of Pathology 4828:Nieves, D; Moreno, J. J. (2006). 4599:Powell, W. S.; Rokach, J (2013). 7988:Tooltip Leukotriene D4 hydrolase 7957:Tooltip Leukotriene C4 hydrolase 7836:Tooltip Leukotriene A4 hydrolase 6521:Arachidonic acid 5-hydroperoxide 6272:15-LOX BRENDA homo sapiens entry 4189:10.1111/j.1742-4658.2007.05909.x 2379:and could serve to recruit this 2182:)-HETE induce the generation of 2084:; and diverse types of vascular 2056:)-HETE bind to and activate the 1452:)-eicosatrienoic acid (14,15-HXA 1260:configuration to carbon 14. EXC 1149:)-HETE thereby forming their 15( 965:but also to small amounts of 11( 651:15-HpETE stereoisomers, i.e. 15( 300: 22: 17:15-Hydroxyeicosatetraenoic acid 8081:Prostanoid signaling modulators 7925:Tooltip Leukotriene C4 synthase 7064:Tooltip Leukotriene B4 receptor 6306: 6165: 6116: 6026: 5977: 5928: 5832:Chemico-Biological Interactions 5773: 5722: 5713: 5672: 5636: 5601: 5565: 5516: 5428: 5394:International Journal of Cancer 5384: 5341: 5313:Journal of Biological Chemistry 5300: 5272: 5189: 5129: 5086: 5051: 4911: 4862: 4782: 4654:Journal of Biological Chemistry 4641: 4592: 4557: 4516: 4440:Journal of Biological Chemistry 4427: 4399:Journal of Biological Chemistry 4386: 4345: 4319:Chemical Research in Toxicology 4278:Journal of Biological Chemistry 4163: 4127:Drug Metabolism and Disposition 4114: 4076:Journal of Biological Chemistry 4059: 4010: 3908: 3849: 3814: 3646:10.1152/ajplung.1999.277.3.L457 3625: 3587:Journal of Biological Chemistry 3383: 3334: 3299: 3258: 3219: 3191: 3156: 3095: 3054: 2924:10.1152/ajplung.1992.262.4.L392 2582:Schneider, C; Pozzi, A (2011). 2301:) thereby blocking this cell's 1865:(i.e. 5-oxo-ETE), respectively. 1793:-eicosatetraenoic acid) or to 5 1761:-eicosatetraenoic acid) and LXB 1516:of 13-hydroxy-14,15-cis-epoxy-5 1161:-2 position can be attacked by 350:15-Hydroxyeicosatetraenoic acid 334:(at 25 °C , 100 kPa). 5011:)-HPETE is angiostatic and 15( 4875:Journal of Cellular Physiology 3104:"Spatial requirements for 15-( 2903: 2862: 2821: 2764: 2678: 1859:5-hydroxyeicosatetraenoic acid 1721:Oxygenated by 5-lipoxygenase ( 1326:Metabolized by 15-LOX-2 to 11( 1200:-eicosatetraenoic acid (i.e., 1093:)-HETE by ubiquitous cellular 1025:of arachidonic acid yields 15( 977:)-HETE. When pretreated with 839:)-hydroxyeicosatetraenoic acid 599:at carbon position 15. Its 15( 551:Nomenclature and stereoisomers 306: 294: 1: 8911:Receptor/signaling modulators 8074:Receptor/signaling modulators 6235:10.1517/13543776.2016.1113259 6039:The Journal of Lipid Research 5541:10.1016/S0002-9440(10)65117-6 5060:Biochemistry and Cell Biology 4980:10.1158/0008-5472.CAN-05-0633 4834:The Journal of Lipid Research 4617:10.1016/j.plipres.2013.09.001 4542:10.1016/S0021-9258(18)34537-X 3511:10.1016/S0021-9258(20)89485-X 3016:The Journal of Lipid Research 2888:10.1016/S0021-9258(18)89853-2 2847:10.1016/S0021-9258(19)68801-0 2746:New Horizons (Baltimore, Md.) 2588:Cancer and Metastasis Reviews 2528: 2437:5-Hydroxyicosatetraenoic acid 2288: 2232: 2015: 1350:)-eicosatrienoic acid and 13( 931:) in greater amounts than 15( 702: 6142:10.4049/jimmunol.157.10.4664 6102:10.1016/j.bbalip.2005.08.009 5622:10.1016/0167-4889(92)90113-p 5164:10.1371/journal.pone.0111006 4933:10.1016/0005-2760(93)90223-v 4804:10.1016/j.biocel.2013.02.018 4768:10.1016/j.biocel.2013.05.009 4719:10.1371/journal.pone.0063076 4578:10.1016/0005-2760(89)90264-6 3930:10.1016/0005-2760(93)90085-n 3835:10.1016/0006-291x(81)91258-4 3552:10.1016/0003-9861(87)90589-3 3404:10.1016/0003-9861(92)90704-z 3320:10.1016/0003-9861(88)90246-9 3244:10.1016/0090-6980(80)90156-2 3177:10.1016/0005-2760(93)90106-j 3071:10.1007/978-1-4615-4861-4_13 2798:10.1016/0014-5793(75)80439-x 2654:10.1016/j.immuni.2014.02.009 1817:-eicosatetraenoate (i.e., 5( 1651:; 15-oxo-ETE, similar to 15( 1566:gene) to make two products, 943:)-HpETE or the leukotriene A 7: 8654:Muraglitazar (muroglitazar) 6452:(Prostacyclin/Epoprostenol) 5941:Annual Review of Physiology 4502:10.1016/j.plefa.2005.05.002 4035:10.1152/ajpheart.00349.2009 2506: 2450: 2441:5-Oxo-eicosatetraenoic acid 2269:)-nonenal, 4-hydroperoxy-2( 2261:)-HpETE may, similar to 15( 2209:)-nonenal, 4-hydroperoxy-2( 1863:5-oxo-eicosatetraenoic acid 1466:)-hydroxy-11,12-cis-epoxy-5 1145:) and may be reduced to 15( 995:: Human and rat microsomal 773:-eicosatetraenoic acid (12( 695:-eicosatetraenoic acid (15( 671:-eicosatetraenoic acid (15( 10: 8964: 8506:15-Deoxy-Δ-prostaglandin J 6191:10.4049/jimmunol.157.1.336 5107:10.1016/j.resp.2014.10.015 4847:10.1194/jlr.M600212-JLR200 4605:Progress in Lipid Research 4222:Int. Arch. Allergy Immunol 3792:10.1016/j.jaci.2010.07.015 2413:G protein-coupled receptor 2205:)-HpETE, e.g. 4-hydroxy-2( 2058:G protein-coupled receptor 1706:)-HETE most likely at the 731:by reactions that involve 8902: 8838: 8478: 8450:Tetradecylthioacetic acid 8357: 8324:Tetradecylthioacetic acid 8138: 8065: 8013: 7978: 7946: 7914: 7887: 7825: 7787: 7749: 7610: 7593: 7553: 7490: 7317: 7303: 7214: 7071: 7057: 7040: 6708: 6670: 6623: 6607: 6597: 6556: 6529: 6513: 6503: 6469: 6440: 6394: 6375: 6368: 6349: 6339: 6330: 6314: 5904:10.1016/j.bmc.2014.05.025 5852:10.1016/j.cbi.2014.10.029 5802:10.1016/j.bcp.2007.04.005 5719:Cells. 32:1021-1027, 2011 5029:10.1007/s00011-012-0463-5 3359:10.1016/j.abb.2007.03.012 2704:10.1007/s12576-012-0196-9 2600:10.1007/s10555-011-9310-3 2558:10.1016/j.bcp.2008.07.033 2462: 2082:baby hamster kidney cells 2062:leukotriene B4 receptor 2 1659:)-HpETE, conjugated with 328: 281: 261: 236: 79: 67: 35: 30: 21: 5790:Biochemical Pharmacology 5685:Acta Biochimica Polonica 5350:Biochemistry. Biokhimiia 2546:Biochemical Pharmacology 2409:oxoeicosanoid receptor 1 1700:phosphatidylethanolamine 1212:), and thereafter to 14( 1129:phosphatidylethanolamine 1076:transcellular metabolism 833:-eicosatetraenoic acid ( 627:-eicosatetraenoic acid. 70:15-HETE, 15(S)-HETE, 15( 8034:Dihomo-γ-linolenic acid 6267:15-LOX Gene Atlas entry 5362:10.1023/A:1020526119866 5199:Journal of Biochemistry 5015:)-HETE is angiogenic". 4453:10.1074/jbc.M109.078428 4089:10.1074/jbc.M109.025627 3974:(inactive 2024-04-05). 3699:10.1073/pnas.0710127105 3600:10.1074/jbc.M112.405407 3457:10.1073/pnas.87.16.6248 2975:10.1073/pnas.94.12.6148 2685:Zhu, D; Ran, Y (2012). 2309:-induced production of 2184:reactive oxygen species 1690:Acylated into membrane 1597:Converted to its 14,15- 1420:)-eicosatrienoic acid ( 1246:leukotriene C4 synthase 1111:glutathione peroxidases 388:)-HpETE). This initial 376:, i.e. a metabolite of 8689:Perfluorononanoic acid 8299:Perfluorooctanoic acid 8294:Perfluorononanoic acid 6002:10.1124/mol.109.057489 5990:Molecular Pharmacology 5698:10.18388/abp.2009_2506 5658:10.1006/bbrc.2000.2597 5326:10.1074/jbc.M111936200 5250:10.1124/mol.109.060541 5238:Molecular Pharmacology 4667:10.1074/jbc.M011361200 4412:10.1074/jbc.M611776200 4371:10.1182/blood.V91.1.64 4291:10.1074/jbc.M504178200 4139:10.1124/dmd.110.035121 3883:10.1073/pnas.78.9.5523 3141:10.1074/jbc.275.9.6586 2385:inflammatory responses 2094:pulmonary hypertension 1900:)-nonenal and 4-oxo-2( 1687:)-eicosatrienoic acid. 1539:(CYP) enzymes such as 1165:to form corresponding 1089:Rapidly reduced to 15( 1003:of 15-HETEs, i.e., 15( 589:absolute configuration 443:Some cell types (e.g. 8284:Palmitoylethanolamide 7970:Serine-borate complex 7136:CGS-23131 (LY-223982) 6178:Journal of Immunology 6129:Journal of Immunology 5072:10.1139/bcb-2013-0037 5017:Inflammation Research 3972:10.5655/smr.v4i2.1004 3640:(3 Pt 1): L457–L464. 2918:(4 Pt 1): L392–L398. 1440:)-cysteinyl-glycyl-(5 1125:phosphatidylinositols 1103:prostacyclin synthase 1053:. Cells forming this 420:)-HETE), a subset of 8501:5-Oxo-15-hydroxy-ETE 8171:Aluminium clofibrate 7906:17-Octadecynoic acid 7676:Hypericum perforatum 5454:10.1167/iovs.04-1166 2338:=1 μM) inhibitor of 1696:phosphatidylinositol 1558:Metabolized in skin 1107:thromboxane synthase 993:Microsome metabolism 947:isomer cited above. 869:-14,15-leukotriene A 707:Human cells release 412:)-diHETE), 5-oxo-15( 37:Preferred IUPAC name 8001:Ubenimex (bestatin) 7879:Ubenimex (bestatin) 6717:bronchoconstriction 6052:10.1194/jlr.M040741 5844:2015CBI...234..144S 5319:(18): 16189–16201. 5155:2014PLoSO...9k1006P 4710:2013PLoSO...863076O 4660:(15): 12454–12459. 4405:(28): 20151–20163. 4284:(31): 28337–28346. 4082:(45): 31280–31290. 3960:Southern Med Review 3874:1981PNAS...78.5523M 3690:2008PNAS..105..680F 3593:(50): 41651–41666. 3448:1990PNAS...87.6248B 3029:10.1194/jlr.M001719 2966:1997PNAS...94.6148B 2881:(22): 14048–14053. 2789:1975FEBSL..60..149S 2375:activity for human 2273:)-nonenal, 4-oxo-2( 2213:)-nonenal, 4-oxo-2( 2098:portal hypertension 973:)-HETE and ~78% 15( 637:cis–trans isomerism 536:paracrine signaling 324: g·mol 18: 7769:3-Methoxytropolone 7693:N-Stearoyldopamine 5494:10.1042/BA20070264 2435:cancer cells (see 2307:lipopolysaccharide 2155:)-HpETE and/or 15( 1861:(i.e. 5-HETE) and 1216:)-glutothionyl-15( 1065:Further metabolism 491:stereoisomers. 15( 338:Infobox references 16: 8920: 8919: 8279:Oleylethanolamide 8090: 8089: 8009: 8008: 7678:(St. John's Wort) 7604: 7589: 7588: 7585: 7584: 7299: 7298: 7051: 6994: 6993: 6666: 6665: 6593: 6592: 6499: 6498: 6465: 6464: 6461: 6460: 6135:(10): 4664–4671. 6045:(11): 3070–3077. 5898:(15): 4293–4297. 5748:10.7717/peerj.635 5488:(Pt 2): 121–133. 5406:10.1002/ijc.11447 5211:10.1093/jb/mvq010 4973:(16): 7283–7291. 4888:10.1002/jcp.24443 4446:(10): 6891–6903. 4331:10.1021/tx700130p 4325:(11): 1665–1675. 4234:10.1159/000351422 4182:(14): 3494–3502. 3786:(4): 859–867.e9. 3504:(12): 7570–7577. 3442:(16): 6248–6252. 3080:978-0-306-46044-9 2960:(12): 6148–6152. 2840:(18): 9579–9582. 2368:colorectal cancer 2086:endothelial cells 1801:)-dihydroperoxy-6 1408:)-glutathionyl-(5 905:15-Lipoxygenase-2 743:15-Lipoxygenase-1 607:is designated 15( 346:Chemical compound 344: 343: 121:Interactive image 8955: 8771: 8767: 8529:Arachidonic acid 8486: 8482: 8385:Arachidonic acid 8365: 8361: 8176:Arachidonic acid 8146: 8142: 8130: 8126: 8117: 8110: 8103: 8094: 8093: 8044:Arachidonic acid 7989: 7985: 7958: 7954: 7926: 7922: 7899: 7895: 7837: 7833: 7795: 7791: 7757: 7753: 7717: 7713: 7618: 7614: 7608: 7607: 7598: 7564: 7560: 7501: 7497: 7328: 7324: 7315: 7314: 7311: 7307: 7225: 7221: 7082: 7078: 7069: 7068: 7065: 7061: 7055: 7054: 7045: 7021: 7014: 7007: 6998: 6997: 6768:vasoconstriction 6605: 6604: 6511: 6510: 6373: 6372: 6347: 6346: 6337: 6336: 6322:Arachidonic acid 6301: 6294: 6287: 6278: 6277: 6255: 6254: 6218: 6212: 6211: 6193: 6169: 6163: 6162: 6144: 6120: 6114: 6113: 6084: 6075: 6074: 6064: 6054: 6030: 6024: 6023: 6013: 5981: 5975: 5974: 5964: 5932: 5926: 5925: 5915: 5883: 5874: 5873: 5863: 5823: 5814: 5813: 5784:)-HPETE and 15-( 5777: 5771: 5770: 5760: 5750: 5726: 5720: 5717: 5711: 5710: 5700: 5676: 5670: 5669: 5640: 5634: 5633: 5605: 5599: 5598: 5581:(1–4): 135–146. 5569: 5563: 5562: 5552: 5520: 5514: 5513: 5476: 5467: 5466: 5456: 5432: 5426: 5425: 5388: 5382: 5381: 5356:(9): 1021–1026. 5345: 5339: 5338: 5328: 5304: 5298: 5297: 5276: 5270: 5269: 5232: 5223: 5222: 5193: 5187: 5186: 5176: 5166: 5133: 5127: 5126: 5090: 5084: 5083: 5055: 5049: 5048: 5004: 4993: 4992: 4982: 4954: 4945: 4944: 4915: 4909: 4908: 4890: 4866: 4860: 4859: 4849: 4825: 4816: 4815: 4798:(6): 1031–1041. 4786: 4780: 4779: 4762:(8): 1620–1628. 4751: 4742: 4741: 4731: 4721: 4689: 4680: 4679: 4669: 4645: 4639: 4638: 4628: 4596: 4590: 4589: 4561: 4555: 4554: 4544: 4520: 4514: 4513: 4496:(3–4): 141–162. 4485: 4476: 4475: 4465: 4455: 4431: 4425: 4424: 4414: 4390: 4384: 4383: 4373: 4349: 4343: 4342: 4313: 4304: 4303: 4293: 4269: 4254: 4253: 4216: 4210: 4209: 4191: 4167: 4161: 4160: 4150: 4118: 4112: 4111: 4101: 4091: 4063: 4057: 4056: 4046: 4029:(2): H495–H507. 4014: 4008: 4007: 4001: 3993: 3983: 3951: 3942: 3941: 3912: 3906: 3905: 3895: 3885: 3868:(9): 5523–5527. 3853: 3847: 3846: 3818: 3812: 3811: 3771: 3762: 3761: 3744:(3–4): 120–125. 3733: 3722: 3721: 3711: 3701: 3669: 3658: 3657: 3629: 3623: 3622: 3612: 3602: 3577: 3564: 3563: 3535: 3524: 3523: 3513: 3489: 3480: 3479: 3469: 3459: 3427: 3416: 3415: 3387: 3381: 3380: 3370: 3338: 3332: 3331: 3303: 3297: 3296: 3286: 3262: 3256: 3255: 3223: 3217: 3216: 3195: 3189: 3188: 3171:(2–3): 258–263. 3160: 3154: 3153: 3143: 3134:(9): 6586–6591. 3099: 3093: 3092: 3058: 3052: 3051: 3041: 3031: 3007: 2998: 2997: 2987: 2977: 2945: 2936: 2935: 2907: 2901: 2900: 2890: 2866: 2860: 2859: 2849: 2825: 2819: 2818: 2800: 2768: 2762: 2761: 2741: 2735: 2734: 2716: 2706: 2682: 2676: 2675: 2665: 2633: 2622: 2621: 2611: 2594:(3–4): 277–294. 2579: 2570: 2569: 2541: 2381:white blood cell 2332:oxidative stress 1947:viz., 15-epi-LXA 1873:)-HpETE may be: 1710:-2 position. 15( 1514:diastereoisomers 1173:)-HETE at their 1085:)-HpETE may be: 1051:oxidative stress 1015:) stereoisomer. 997:cytochrome P450s 953:: Cells can use 777:)-HpETE) and 14( 709:arachidonic acid 675:)-HpETE) and 15( 597:functional group 463:. Similar to 15( 378:arachidonic acid 323: 308: 302: 296: 289:Chemical formula 229: 209: 198: 184: 165: 154: 143: 123: 99: 26: 19: 15: 8963: 8962: 8958: 8957: 8956: 8954: 8953: 8952: 8923: 8922: 8921: 8916: 8898: 8834: 8769: 8702: 8699:Prostaglandin J 8509: 8484: 8474: 8363: 8353: 8254: 8144: 8134: 8128: 8121: 8091: 8086: 8061: 8057: 8005: 7987: 7984: 7974: 7956: 7952: 7942: 7924: 7920: 7910: 7897: 7893: 7883: 7835: 7831: 7821: 7793: 7783: 7755: 7745: 7715: 7616: 7597: 7581: 7577: 7562: 7559: 7549: 7530: 7522: 7514: 7499: 7496: 7486: 7357: 7349: 7341: 7326: 7323: 7309: 7295: 7271: 7263: 7223: 7220: 7210: 7126: 7108: 7100: 7080: 7077: 7063: 7044: 7036: 7025: 6995: 6990: 6983: 6974: 6954: 6934: 6926: 6911: 6903: 6885: 6877: 6862: 6842: 6834: 6826: 6818: 6810: 6793: 6785: 6777: 6758: 6750: 6742: 6734: 6726: 6704: 6694: 6687: 6662: 6658: 6650: 6642: 6634: 6619: 6589: 6585: 6577: 6569: 6552: 6548: 6540: 6525: 6495: 6491: 6483: 6457: 6451: 6436: 6430: 6419: 6408: 6390: 6386: 6364: 6360: 6326: 6310: 6305: 6263: 6258: 6219: 6215: 6170: 6166: 6121: 6117: 6085: 6078: 6031: 6027: 5982: 5978: 5933: 5929: 5884: 5877: 5824: 5817: 5778: 5774: 5727: 5723: 5718: 5714: 5677: 5673: 5641: 5637: 5606: 5602: 5570: 5566: 5521: 5517: 5477: 5470: 5433: 5429: 5389: 5385: 5346: 5342: 5305: 5301: 5282:Cancer Research 5277: 5273: 5233: 5226: 5194: 5190: 5149:(10): e111006. 5134: 5130: 5091: 5087: 5056: 5052: 5005: 4996: 4967:Cancer Research 4955: 4948: 4916: 4912: 4867: 4863: 4826: 4819: 4787: 4783: 4752: 4745: 4690: 4683: 4646: 4642: 4597: 4593: 4562: 4558: 4535:(12): 7056–67. 4521: 4517: 4486: 4479: 4432: 4428: 4391: 4387: 4350: 4346: 4314: 4307: 4270: 4257: 4217: 4213: 4168: 4164: 4119: 4115: 4064: 4060: 4015: 4011: 3995: 3994: 3952: 3945: 3913: 3909: 3854: 3850: 3819: 3815: 3772: 3765: 3734: 3725: 3670: 3661: 3630: 3626: 3578: 3567: 3536: 3527: 3490: 3483: 3428: 3419: 3388: 3384: 3339: 3335: 3304: 3300: 3263: 3259: 3224: 3220: 3196: 3192: 3161: 3157: 3100: 3096: 3081: 3059: 3055: 3008: 3001: 2946: 2939: 2908: 2904: 2867: 2863: 2826: 2822: 2769: 2765: 2742: 2738: 2683: 2679: 2634: 2625: 2580: 2573: 2542: 2535: 2531: 2509: 2482:are analogs of 2465: 2453: 2419:, particularly 2397: 2340:12-lipoxygenase 2337: 2291: 2277:)-nonenal, and 2245:)-HpETE and 15( 2239: 2225:)-decanal, are 2217:)-nonenal, and 2194:)-HpETE and 15( 2170:)-HpETE and 15( 2115:)-HpETE and 15( 2052:)-HpETE and 15( 2031: 2025:)-HpETE and 15( 2018: 1982: 1950: 1946: 1942: 1912:)-HETE may be: 1764: 1732: 1694:, particularly 1632:)-HETE may be: 1570:(HxA3, i.e., 13 1537:cytochrome P450 1535:Metabolized by 1530:cytochrome P450 1455: 1436:)-dihydroxy-14( 1425: 1404:)-dihydroxy-14( 1395: 1390: 1383: 1298: 1291: 1284: 1277: 1271: 1267: 1263: 1251: 1243: 1239: 1211: 1207: 1163:phospholipase C 1123:, particularly 1067: 1055:racemic mixture 1033:)-hydroperoxy-5 1001:racemic mixture 946: 935:)-HpETE and 15( 915:)-HpETE and 15( 900: 872: 805:)-HpETE and 12( 757:)-hydroperoxy-5 733:phospholipase C 705: 679:)-hydroperoxy-5 655:)-hydroperoxy-5 595:of the hydroxy 553: 495:)-HpETE and 15( 347: 340: 335: 321: 311: 305: 299: 291: 277: 274: 269: 268: 257: 254: 253: 250: 244: 243: 232: 212: 199: 187: 174: 146: 126: 113: 102: 89: 75: 63: 62: 12: 11: 5: 8961: 8951: 8950: 8945: 8940: 8935: 8918: 8917: 8915: 8914: 8907: 8903: 8900: 8899: 8897: 8896: 8891: 8886: 8881: 8876: 8871: 8866: 8861: 8856: 8851: 8842: 8840: 8836: 8835: 8833: 8832: 8823: 8822: 8817: 8812: 8807: 8798: 8797: 8792: 8787: 8782: 8777: 8760: 8759: 8754: 8749: 8744: 8739: 8734: 8729: 8724: 8719: 8714: 8709: 8704: 8700: 8696: 8691: 8686: 8681: 8676: 8671: 8666: 8661: 8656: 8651: 8646: 8641: 8636: 8631: 8626: 8621: 8616: 8611: 8606: 8601: 8596: 8591: 8586: 8581: 8576: 8571: 8566: 8561: 8556: 8551: 8546: 8541: 8536: 8531: 8526: 8521: 8516: 8511: 8507: 8503: 8498: 8489: 8487: 8476: 8475: 8473: 8472: 8467: 8462: 8453: 8452: 8447: 8442: 8437: 8432: 8427: 8422: 8417: 8412: 8407: 8402: 8397: 8392: 8387: 8382: 8377: 8368: 8366: 8355: 8354: 8352: 8351: 8346: 8337: 8336: 8331: 8326: 8321: 8316: 8311: 8306: 8301: 8296: 8291: 8286: 8281: 8276: 8271: 8266: 8261: 8256: 8252: 8248: 8243: 8238: 8233: 8228: 8223: 8218: 8213: 8212:) (in rodents) 8203: 8198: 8193: 8188: 8183: 8178: 8173: 8168: 8163: 8158: 8149: 8147: 8136: 8135: 8120: 8119: 8112: 8105: 8097: 8088: 8087: 8085: 8084: 8077: 8070: 8066: 8063: 8062: 8060: 8059: 8055: 8051: 8046: 8041: 8039:Diacylglycerol 8036: 8031: 8026: 8017: 8015: 8011: 8010: 8007: 8006: 8004: 8003: 7998: 7992: 7990: 7982: 7976: 7975: 7973: 7972: 7967: 7961: 7959: 7950: 7944: 7943: 7941: 7940: 7935: 7929: 7927: 7918: 7912: 7911: 7909: 7908: 7902: 7900: 7891: 7885: 7884: 7882: 7881: 7876: 7871: 7866: 7861: 7856: 7851: 7846: 7840: 7838: 7829: 7823: 7822: 7820: 7819: 7814: 7809: 7804: 7798: 7796: 7785: 7784: 7782: 7781: 7776: 7771: 7766: 7760: 7758: 7747: 7746: 7744: 7743: 7738: 7733: 7728: 7723: 7706: 7705: 7700: 7695: 7690: 7685: 7680: 7672: 7667: 7662: 7657: 7652: 7647: 7642: 7637: 7632: 7627: 7621: 7619: 7605: 7591: 7590: 7587: 7586: 7583: 7582: 7580: 7579: 7575: 7567: 7565: 7557: 7551: 7550: 7548: 7547: 7542: 7533: 7532: 7528: 7524: 7520: 7516: 7512: 7504: 7502: 7494: 7488: 7487: 7485: 7484: 7479: 7474: 7469: 7464: 7459: 7454: 7449: 7444: 7439: 7434: 7429: 7424: 7419: 7414: 7409: 7404: 7399: 7394: 7389: 7384: 7379: 7374: 7369: 7360: 7359: 7355: 7351: 7347: 7343: 7339: 7331: 7329: 7321: 7312: 7301: 7300: 7297: 7296: 7294: 7293: 7288: 7283: 7274: 7273: 7269: 7265: 7261: 7260:20-Hydroxy-LTB 7257: 7252: 7247: 7242: 7237: 7228: 7226: 7218: 7212: 7211: 7209: 7208: 7203: 7198: 7193: 7188: 7183: 7178: 7173: 7168: 7163: 7158: 7153: 7148: 7143: 7138: 7133: 7128: 7124: 7123:20-Carboxy-LTB 7116: 7115: 7110: 7106: 7102: 7098: 7097:20-Hydroxy-LTB 7094: 7085: 7083: 7075: 7066: 7052: 7038: 7037: 7024: 7023: 7016: 7009: 7001: 6992: 6991: 6989: 6988: 6987: 6986: 6981: 6977: 6976:(Dinoprostone) 6972: 6959: 6958: 6957: 6956: 6952: 6939: 6938: 6937: 6936: 6932: 6928: 6924: 6915: 6914: 6913: 6909: 6905: 6901: 6889: 6888: 6887: 6883: 6879: 6875: 6866: 6865: 6864: 6860: 6847: 6846: 6845: 6844: 6840: 6836: 6832: 6828: 6824: 6820: 6816: 6812: 6808: 6797: 6796: 6795: 6791: 6787: 6783: 6779: 6775: 6763: 6762: 6761: 6760: 6756: 6752: 6748: 6744: 6740: 6736: 6732: 6728: 6724: 6712: 6710: 6706: 6705: 6703: 6702: 6697: 6692: 6685: 6676: 6674: 6668: 6667: 6664: 6663: 6661: 6660: 6656: 6652: 6648: 6644: 6640: 6636: 6632: 6627: 6625: 6621: 6620: 6618: 6617: 6611: 6609: 6602: 6595: 6594: 6591: 6590: 6588: 6587: 6583: 6579: 6575: 6571: 6567: 6562: 6560: 6554: 6553: 6551: 6550: 6546: 6542: 6538: 6533: 6531: 6527: 6526: 6524: 6523: 6517: 6515: 6508: 6501: 6500: 6497: 6496: 6494: 6493: 6489: 6485: 6481: 6476: 6474: 6467: 6466: 6463: 6462: 6459: 6458: 6456: 6455: 6449: 6444: 6442: 6438: 6437: 6435: 6434: 6428: 6423: 6422: 6417: 6412: 6411: 6409:(Dinoprostone) 6406: 6401: 6399: 6392: 6391: 6389: 6388: 6384: 6379: 6377: 6370: 6366: 6365: 6363: 6362: 6358: 6353: 6351: 6344: 6341:Prostaglandins 6334: 6328: 6327: 6325: 6324: 6318: 6316: 6312: 6311: 6304: 6303: 6296: 6289: 6281: 6275: 6274: 6269: 6262: 6261:External links 6259: 6257: 6256: 6213: 6184:(1): 336–342. 6164: 6115: 6096:(3): 228–236. 6076: 6025: 5996:(3): 516–525. 5976: 5927: 5875: 5815: 5796:(2): 202–214. 5772: 5721: 5712: 5691:(4): 711–715. 5671: 5652:(2): 345–350. 5635: 5616:(3): 247–252. 5600: 5564: 5535:(1): 235–245. 5515: 5468: 5447:(3): 849–856. 5427: 5400:(5): 837–843. 5383: 5340: 5299: 5288:(2): 497–503. 5271: 5244:(2): 171–184. 5224: 5205:(5): 751–764. 5188: 5128: 5085: 5066:(6): 498–505. 5050: 5023:(7): 707–718. 4994: 4946: 4927:(1): 102–108. 4910: 4881:(2): 245–257. 4861: 4840:(12): 2681–9. 4817: 4781: 4743: 4681: 4640: 4611:(4): 651–665. 4591: 4572:(2): 158–168. 4556: 4515: 4477: 4426: 4385: 4344: 4305: 4255: 4228:(2): 135–142. 4211: 4162: 4133:(2): 180–190. 4113: 4058: 4009: 3943: 3907: 3848: 3829:(3): 976–986. 3813: 3763: 3723: 3684:(2): 680–685. 3659: 3624: 3565: 3546:(2): 444–450. 3525: 3481: 3417: 3398:(2): 407–411. 3382: 3353:(2): 159–168. 3333: 3314:(1): 162–170. 3298: 3257: 3232:Prostaglandins 3218: 3190: 3155: 3094: 3079: 3053: 3022:(3): 575–585. 2999: 2937: 2902: 2861: 2820: 2783:(1): 149–152. 2763: 2752:(4): 550–562. 2736: 2697:(3): 163–172. 2677: 2648:(3): 315–327. 2623: 2571: 2532: 2530: 2527: 2526: 2525: 2520: 2515: 2508: 2505: 2492:leukotriene D4 2484:leukotriene A4 2464: 2461: 2452: 2449: 2396: 2389: 2335: 2295:THP1 cell line 2290: 2287: 2241:Similar to 15( 2238: 2231: 2030: 2019: 2017: 2014: 2013: 2012: 1980: 1963:)-trihydroxy-7 1948: 1944: 1940: 1927:Similar to 15( 1925: 1916:Similar to 15( 1906: 1905: 1892:Similar to 15( 1890: 1885:)-HpETE to 15( 1877:Reduced to 15( 1867: 1866: 1777:)-trihydroxy-6 1762: 1745:)-trihydroxy-7 1730: 1719: 1688: 1645:prostaglandins 1626: 1625: 1602: 1595: 1556: 1555:to 15-oxo-ETE. 1533: 1532:, i.e. CYP2J2. 1505:Isomerized to 1503: 1457: 1453: 1423: 1393: 1388: 1381: 1324: 1301: 1296: 1289: 1282: 1275: 1269: 1265: 1261: 1249: 1241: 1237: 1209: 1205: 1178: 1157:)-HETE in the 1119:into membrane 1114: 1109:, and various 1066: 1063: 963:prostaglandins 951:Cyclooxygenase 944: 898: 870: 813:)-HETE and 12( 704: 701: 587:refers to the 563:name viz., 15( 552: 549: 475:)-HETE. These 461:auto-oxidation 436:)-HETE and 15( 345: 342: 341: 336: 332:standard state 329: 326: 325: 319: 313: 312: 309: 303: 297: 292: 287: 284: 283: 279: 278: 276: 275: 272: 264: 263: 262: 259: 258: 256: 255: 251: 248: 247: 239: 238: 237: 234: 233: 231: 230: 222: 220: 214: 213: 211: 210: 202: 200: 192: 189: 188: 186: 185: 177: 175: 170: 167: 166: 156: 148: 147: 145: 144: 136: 134: 128: 127: 125: 124: 116: 114: 107: 104: 103: 101: 100: 92: 90: 85: 82: 81: 77: 76: 69: 65: 64: 40: 39: 33: 32: 28: 27: 9: 6: 4: 3: 2: 8960: 8949: 8946: 8944: 8941: 8939: 8936: 8934: 8931: 8930: 8928: 8913: 8912: 8908: 8905: 8904: 8901: 8895: 8892: 8890: 8889:Rivoglitazone 8887: 8885: 8882: 8880: 8879:Netoglitazone 8877: 8875: 8872: 8870: 8867: 8865: 8862: 8860: 8857: 8855: 8852: 8850: 8847: 8844: 8843: 8841: 8839:Non-selective 8837: 8831: 8828: 8825: 8824: 8821: 8818: 8816: 8813: 8811: 8808: 8806: 8803: 8800: 8799: 8796: 8793: 8791: 8788: 8786: 8783: 8781: 8778: 8776: 8773: 8768: 8762: 8761: 8758: 8755: 8753: 8750: 8748: 8745: 8743: 8742:Sodelglitazar 8740: 8738: 8735: 8733: 8730: 8728: 8725: 8723: 8722:Rosiglitazone 8720: 8718: 8717:Rivoglitazone 8715: 8713: 8710: 8708: 8705: 8703: 8697: 8695: 8692: 8690: 8687: 8685: 8682: 8680: 8677: 8675: 8672: 8670: 8669:Netoglitazone 8667: 8665: 8662: 8660: 8657: 8655: 8652: 8650: 8649:Lobeglitazone 8647: 8645: 8642: 8640: 8637: 8635: 8632: 8630: 8627: 8625: 8622: 8620: 8617: 8615: 8612: 8610: 8607: 8605: 8602: 8600: 8597: 8595: 8592: 8590: 8587: 8585: 8582: 8580: 8577: 8575: 8572: 8570: 8567: 8565: 8562: 8560: 8557: 8555: 8552: 8550: 8547: 8545: 8542: 8540: 8537: 8535: 8534:Balaglitazone 8532: 8530: 8527: 8525: 8522: 8520: 8517: 8515: 8512: 8510: 8504: 8502: 8499: 8497: 8494: 8491: 8490: 8488: 8483: 8477: 8471: 8468: 8466: 8463: 8461: 8458: 8455: 8454: 8451: 8448: 8446: 8445:Sodelglitazar 8443: 8441: 8438: 8436: 8433: 8431: 8428: 8426: 8423: 8421: 8418: 8416: 8413: 8411: 8408: 8406: 8403: 8401: 8398: 8396: 8393: 8391: 8388: 8386: 8383: 8381: 8378: 8376: 8373: 8370: 8369: 8367: 8362: 8356: 8350: 8347: 8345: 8342: 8339: 8338: 8335: 8332: 8330: 8327: 8325: 8322: 8320: 8317: 8315: 8314:Sodelglitazar 8312: 8310: 8307: 8305: 8302: 8300: 8297: 8295: 8292: 8290: 8287: 8285: 8282: 8280: 8277: 8275: 8272: 8270: 8269:Lobeglitazone 8267: 8265: 8262: 8260: 8257: 8255: 8251:Leukotriene B 8249: 8247: 8244: 8242: 8239: 8237: 8234: 8232: 8229: 8227: 8224: 8222: 8219: 8217: 8214: 8211: 8207: 8204: 8202: 8199: 8197: 8194: 8192: 8189: 8187: 8184: 8182: 8179: 8177: 8174: 8172: 8169: 8167: 8164: 8162: 8159: 8157: 8154: 8151: 8150: 8148: 8143: 8137: 8133: 8127: 8118: 8113: 8111: 8106: 8104: 8099: 8098: 8095: 8083: 8082: 8078: 8076: 8075: 8071: 8068: 8067: 8064: 8058: 8054:Leukotriene A 8052: 8050: 8047: 8045: 8042: 8040: 8037: 8035: 8032: 8030: 8027: 8025: 8024:Linoleic acid 8022: 8019: 8018: 8016: 8012: 8002: 7999: 7997: 7994: 7993: 7991: 7986: 7977: 7971: 7968: 7966: 7963: 7962: 7960: 7955: 7945: 7939: 7936: 7934: 7931: 7930: 7928: 7923: 7913: 7907: 7904: 7903: 7901: 7896: 7886: 7880: 7877: 7875: 7872: 7870: 7867: 7865: 7862: 7860: 7857: 7855: 7852: 7850: 7847: 7845: 7842: 7841: 7839: 7834: 7824: 7818: 7815: 7813: 7810: 7808: 7805: 7803: 7800: 7799: 7797: 7792: 7786: 7780: 7777: 7775: 7772: 7770: 7767: 7765: 7762: 7761: 7759: 7754: 7748: 7742: 7739: 7737: 7734: 7732: 7729: 7727: 7724: 7722: 7719: 7714: 7708: 7707: 7704: 7701: 7699: 7696: 7694: 7691: 7689: 7686: 7684: 7681: 7679: 7677: 7673: 7671: 7668: 7666: 7663: 7661: 7658: 7656: 7653: 7651: 7648: 7646: 7643: 7641: 7638: 7636: 7633: 7631: 7628: 7626: 7623: 7622: 7620: 7615: 7609: 7606: 7602: 7596: 7592: 7578: 7574:Leukotriene E 7572: 7569: 7568: 7566: 7561: 7552: 7546: 7543: 7541: 7538: 7535: 7534: 7531: 7527:Leukotriene E 7525: 7523: 7519:Leukotriene D 7517: 7515: 7511:Leukotriene C 7509: 7506: 7505: 7503: 7498: 7489: 7483: 7480: 7478: 7475: 7473: 7470: 7468: 7465: 7463: 7460: 7458: 7455: 7453: 7450: 7448: 7445: 7443: 7440: 7438: 7435: 7433: 7430: 7428: 7425: 7423: 7420: 7418: 7415: 7413: 7410: 7408: 7405: 7403: 7400: 7398: 7395: 7393: 7390: 7388: 7385: 7383: 7380: 7378: 7375: 7373: 7370: 7368: 7365: 7362: 7361: 7358: 7354:Leukotriene E 7352: 7350: 7346:Leukotriene D 7344: 7342: 7338:Leukotriene C 7336: 7333: 7332: 7330: 7325: 7316: 7313: 7308: 7302: 7292: 7289: 7287: 7284: 7282: 7279: 7276: 7275: 7272: 7268:Leukotriene B 7266: 7264: 7258: 7256: 7253: 7251: 7248: 7246: 7243: 7241: 7238: 7236: 7233: 7230: 7229: 7227: 7222: 7213: 7207: 7204: 7202: 7199: 7197: 7194: 7192: 7189: 7187: 7184: 7182: 7179: 7177: 7174: 7172: 7169: 7167: 7164: 7162: 7159: 7157: 7154: 7152: 7149: 7147: 7144: 7142: 7139: 7137: 7134: 7132: 7129: 7127: 7121: 7118: 7117: 7114: 7111: 7109: 7105:Leukotriene B 7103: 7101: 7095: 7093: 7090: 7087: 7086: 7084: 7079: 7070: 7067: 7062: 7056: 7053: 7049: 7043: 7039: 7035: 7032: 7029: 7022: 7017: 7015: 7010: 7008: 7003: 7002: 6999: 6984: 6978: 6975: 6969: 6968: 6967: 6965: 6961: 6960: 6955: 6949: 6948: 6947: 6945: 6941: 6940: 6935: 6929: 6927: 6921: 6920: 6919: 6916: 6912: 6906: 6904: 6898: 6897: 6896: 6894: 6890: 6886: 6880: 6878: 6872: 6871: 6870: 6867: 6863: 6857: 6856: 6855: 6853: 6849: 6848: 6843: 6837: 6835: 6829: 6827: 6821: 6819: 6813: 6811: 6805: 6804: 6803: 6802: 6798: 6794: 6788: 6786: 6780: 6778: 6772: 6771: 6770: 6769: 6765: 6764: 6759: 6753: 6751: 6745: 6743: 6737: 6735: 6729: 6727: 6721: 6720: 6719: 6718: 6714: 6713: 6711: 6707: 6701: 6698: 6695: 6688: 6681: 6678: 6677: 6675: 6673: 6669: 6659: 6653: 6651: 6645: 6643: 6637: 6635: 6629: 6628: 6626: 6622: 6616: 6613: 6612: 6610: 6606: 6603: 6600: 6596: 6586: 6580: 6578: 6572: 6570: 6564: 6563: 6561: 6559: 6555: 6549: 6543: 6541: 6535: 6534: 6532: 6528: 6522: 6519: 6518: 6516: 6512: 6509: 6506: 6502: 6492: 6486: 6484: 6478: 6477: 6475: 6472: 6468: 6453: 6446: 6445: 6443: 6439: 6432: 6425: 6424: 6421: 6420:(Alprostadil) 6414: 6413: 6410: 6403: 6402: 6400: 6397: 6393: 6387: 6381: 6380: 6378: 6374: 6371: 6367: 6361: 6355: 6354: 6352: 6348: 6345: 6342: 6338: 6335: 6333: 6329: 6323: 6320: 6319: 6317: 6313: 6309: 6302: 6297: 6295: 6290: 6288: 6283: 6282: 6279: 6273: 6270: 6268: 6265: 6264: 6252: 6248: 6244: 6240: 6236: 6232: 6228: 6224: 6217: 6209: 6205: 6201: 6197: 6192: 6187: 6183: 6179: 6175: 6168: 6160: 6156: 6152: 6148: 6143: 6138: 6134: 6130: 6126: 6119: 6111: 6107: 6103: 6099: 6095: 6091: 6083: 6081: 6072: 6068: 6063: 6058: 6053: 6048: 6044: 6040: 6036: 6029: 6021: 6017: 6012: 6007: 6003: 5999: 5995: 5991: 5987: 5980: 5972: 5968: 5963: 5958: 5954: 5950: 5946: 5942: 5938: 5931: 5923: 5919: 5914: 5909: 5905: 5901: 5897: 5893: 5889: 5882: 5880: 5871: 5867: 5862: 5857: 5853: 5849: 5845: 5841: 5837: 5833: 5829: 5822: 5820: 5811: 5807: 5803: 5799: 5795: 5791: 5787: 5783: 5776: 5768: 5764: 5759: 5754: 5749: 5744: 5740: 5736: 5732: 5725: 5716: 5708: 5704: 5699: 5694: 5690: 5686: 5682: 5675: 5667: 5663: 5659: 5655: 5651: 5647: 5639: 5631: 5627: 5623: 5619: 5615: 5611: 5604: 5596: 5592: 5588: 5584: 5580: 5576: 5568: 5560: 5556: 5551: 5546: 5542: 5538: 5534: 5530: 5526: 5519: 5511: 5507: 5503: 5499: 5495: 5491: 5487: 5483: 5475: 5473: 5464: 5460: 5455: 5450: 5446: 5442: 5438: 5431: 5423: 5419: 5415: 5411: 5407: 5403: 5399: 5395: 5387: 5379: 5375: 5371: 5367: 5363: 5359: 5355: 5351: 5344: 5336: 5332: 5327: 5322: 5318: 5314: 5310: 5303: 5295: 5291: 5287: 5283: 5275: 5267: 5263: 5259: 5255: 5251: 5247: 5243: 5239: 5231: 5229: 5220: 5216: 5212: 5208: 5204: 5200: 5192: 5184: 5180: 5175: 5170: 5165: 5160: 5156: 5152: 5148: 5144: 5140: 5132: 5124: 5120: 5116: 5112: 5108: 5104: 5100: 5096: 5089: 5081: 5077: 5073: 5069: 5065: 5061: 5054: 5046: 5042: 5038: 5034: 5030: 5026: 5022: 5018: 5014: 5010: 5003: 5001: 4999: 4990: 4986: 4981: 4976: 4972: 4968: 4964: 4962: 4953: 4951: 4942: 4938: 4934: 4930: 4926: 4922: 4914: 4906: 4902: 4898: 4894: 4889: 4884: 4880: 4876: 4872: 4865: 4857: 4853: 4848: 4843: 4839: 4835: 4831: 4824: 4822: 4813: 4809: 4805: 4801: 4797: 4793: 4785: 4777: 4773: 4769: 4765: 4761: 4757: 4750: 4748: 4739: 4735: 4730: 4725: 4720: 4715: 4711: 4707: 4704:(5): e63076. 4703: 4699: 4695: 4688: 4686: 4677: 4673: 4668: 4663: 4659: 4655: 4651: 4644: 4636: 4632: 4627: 4622: 4618: 4614: 4610: 4606: 4602: 4595: 4587: 4583: 4579: 4575: 4571: 4567: 4560: 4552: 4548: 4543: 4538: 4534: 4530: 4526: 4519: 4511: 4507: 4503: 4499: 4495: 4491: 4484: 4482: 4473: 4469: 4464: 4459: 4454: 4449: 4445: 4441: 4437: 4430: 4422: 4418: 4413: 4408: 4404: 4400: 4396: 4389: 4381: 4377: 4372: 4367: 4363: 4359: 4355: 4348: 4340: 4336: 4332: 4328: 4324: 4320: 4312: 4310: 4301: 4297: 4292: 4287: 4283: 4279: 4275: 4268: 4266: 4264: 4262: 4260: 4251: 4247: 4243: 4239: 4235: 4231: 4227: 4223: 4215: 4207: 4203: 4199: 4195: 4190: 4185: 4181: 4177: 4173: 4166: 4158: 4154: 4149: 4144: 4140: 4136: 4132: 4128: 4124: 4117: 4109: 4105: 4100: 4095: 4090: 4085: 4081: 4077: 4073: 4069: 4062: 4054: 4050: 4045: 4040: 4036: 4032: 4028: 4024: 4020: 4013: 4005: 3999: 3991: 3987: 3982: 3977: 3973: 3969: 3965: 3961: 3957: 3950: 3948: 3939: 3935: 3931: 3927: 3923: 3919: 3911: 3903: 3899: 3894: 3889: 3884: 3879: 3875: 3871: 3867: 3863: 3859: 3852: 3844: 3840: 3836: 3832: 3828: 3824: 3817: 3809: 3805: 3801: 3797: 3793: 3789: 3785: 3781: 3777: 3770: 3768: 3759: 3755: 3751: 3747: 3743: 3739: 3732: 3730: 3728: 3719: 3715: 3710: 3705: 3700: 3695: 3691: 3687: 3683: 3679: 3675: 3668: 3666: 3664: 3655: 3651: 3647: 3643: 3639: 3635: 3628: 3620: 3616: 3611: 3606: 3601: 3596: 3592: 3588: 3584: 3576: 3574: 3572: 3570: 3561: 3557: 3553: 3549: 3545: 3541: 3534: 3532: 3530: 3521: 3517: 3512: 3507: 3503: 3499: 3495: 3488: 3486: 3477: 3473: 3468: 3463: 3458: 3453: 3449: 3445: 3441: 3437: 3433: 3426: 3424: 3422: 3413: 3409: 3405: 3401: 3397: 3393: 3386: 3378: 3374: 3369: 3364: 3360: 3356: 3352: 3348: 3344: 3337: 3329: 3325: 3321: 3317: 3313: 3309: 3302: 3294: 3290: 3285: 3280: 3276: 3272: 3271:Am. J. Pathol 3268: 3261: 3253: 3249: 3245: 3241: 3237: 3233: 3229: 3222: 3214: 3210: 3206: 3202: 3194: 3186: 3182: 3178: 3174: 3170: 3166: 3159: 3151: 3147: 3142: 3137: 3133: 3129: 3125: 3123: 3119: 3115: 3111: 3107: 3098: 3090: 3086: 3082: 3076: 3072: 3068: 3064: 3057: 3049: 3045: 3040: 3035: 3030: 3025: 3021: 3017: 3013: 3006: 3004: 2995: 2991: 2986: 2981: 2976: 2971: 2967: 2963: 2959: 2955: 2951: 2944: 2942: 2933: 2929: 2925: 2921: 2917: 2913: 2906: 2898: 2894: 2889: 2884: 2880: 2876: 2872: 2865: 2857: 2853: 2848: 2843: 2839: 2835: 2831: 2824: 2816: 2812: 2808: 2804: 2799: 2794: 2790: 2786: 2782: 2778: 2774: 2767: 2759: 2755: 2751: 2747: 2740: 2732: 2728: 2724: 2720: 2715: 2710: 2705: 2700: 2696: 2692: 2688: 2681: 2673: 2669: 2664: 2659: 2655: 2651: 2647: 2643: 2639: 2632: 2630: 2628: 2619: 2615: 2610: 2605: 2601: 2597: 2593: 2589: 2585: 2578: 2576: 2567: 2563: 2559: 2555: 2551: 2547: 2540: 2538: 2533: 2524: 2521: 2519: 2516: 2514: 2511: 2510: 2504: 2501: 2497: 2493: 2489: 2485: 2481: 2477: 2473: 2469: 2460: 2458: 2448: 2446: 2442: 2438: 2434: 2430: 2426: 2422: 2418: 2414: 2410: 2406: 2402: 2395:)-hydroxy-ETE 2394: 2388: 2386: 2382: 2378: 2374: 2369: 2365: 2361: 2357: 2353: 2349: 2345: 2341: 2333: 2328: 2324: 2320: 2316: 2315:interleukin 6 2312: 2308: 2304: 2300: 2296: 2286: 2284: 2281:-4,5-epoxy-2( 2280: 2276: 2272: 2268: 2264: 2260: 2256: 2252: 2248: 2244: 2236: 2230: 2228: 2224: 2221:-4,5-epoxy-2( 2220: 2216: 2212: 2208: 2204: 2199: 2197: 2193: 2189: 2185: 2181: 2177: 2173: 2169: 2164: 2162: 2158: 2154: 2150: 2146: 2142: 2138: 2134: 2130: 2126: 2122: 2118: 2114: 2109: 2107: 2103: 2099: 2095: 2091: 2087: 2083: 2079: 2075: 2071: 2067: 2063: 2059: 2055: 2051: 2046: 2044: 2040: 2036: 2028: 2024: 2010: 2006: 2002: 1998: 1995:)-trihydroxy- 1994: 1990: 1986: 1978: 1974: 1970: 1966: 1962: 1958: 1954: 1938: 1937:diastereomers 1934: 1930: 1926: 1923: 1919: 1915: 1914: 1913: 1911: 1903: 1899: 1895: 1891: 1888: 1884: 1880: 1876: 1875: 1874: 1872: 1864: 1860: 1856: 1852: 1848: 1844: 1840: 1836: 1832: 1828: 1825:)-diHETE). 5( 1824: 1820: 1816: 1812: 1808: 1804: 1800: 1796: 1792: 1788: 1784: 1780: 1776: 1772: 1768: 1760: 1756: 1752: 1748: 1744: 1740: 1736: 1728: 1724: 1720: 1717: 1713: 1709: 1705: 1701: 1697: 1693: 1692:phospholipids 1689: 1686: 1682: 1678: 1674: 1670: 1666: 1662: 1658: 1654: 1650: 1646: 1642: 1638: 1635: 1634: 1633: 1631: 1623: 1621: 1615: 1613: 1607: 1606:electrophiles 1603: 1600: 1596: 1593: 1589: 1585: 1581: 1577: 1573: 1569: 1565: 1561: 1557: 1554: 1550: 1546: 1542: 1538: 1534: 1531: 1527: 1523: 1519: 1515: 1513: 1509: 1504: 1501: 1497: 1493: 1489: 1485: 1481: 1477: 1473: 1469: 1465: 1461: 1458: 1451: 1447: 1443: 1439: 1435: 1431: 1427: 1419: 1415: 1411: 1407: 1403: 1399: 1391: 1384: 1377: 1373: 1369: 1365: 1361: 1357: 1354:)-hydroxy-14( 1353: 1349: 1345: 1341: 1337: 1333: 1330:)-hydroxy-14( 1329: 1325: 1322: 1318: 1314: 1313:diastereomers 1310: 1306: 1302: 1299: 1292: 1285: 1278: 1259: 1255: 1247: 1235: 1231: 1227: 1223: 1219: 1215: 1203: 1199: 1195: 1191: 1187: 1183: 1179: 1177:-2 positions. 1176: 1172: 1168: 1164: 1160: 1156: 1152: 1148: 1144: 1143:Phospholipase 1140: 1139: 1134: 1130: 1126: 1122: 1121:phospholipids 1118: 1115: 1112: 1108: 1104: 1100: 1096: 1092: 1088: 1087: 1086: 1084: 1079: 1077: 1073: 1062: 1060: 1056: 1052: 1048: 1044: 1040: 1036: 1032: 1028: 1024: 1020: 1016: 1014: 1010: 1006: 1002: 998: 994: 990: 988: 984: 980: 976: 972: 968: 964: 960: 956: 952: 948: 942: 938: 934: 930: 926: 922: 921:linoleic acid 918: 914: 911:) to make 15( 910: 906: 902: 896: 892: 888: 884: 880: 877:)-dihydroxy-5 876: 868: 864: 860: 856: 852: 848: 844: 840: 838: 832: 828: 824: 820: 816: 812: 808: 804: 800: 796: 792: 788: 784: 780: 776: 772: 768: 764: 760: 756: 752: 749:) to form 15( 748: 744: 740: 738: 734: 730: 729:phospholipids 726: 722: 718: 714: 710: 700: 698: 694: 690: 686: 682: 678: 674: 670: 666: 662: 658: 654: 650: 646: 642: 638: 634: 630: 626: 622: 618: 614: 610: 606: 602: 598: 594: 590: 586: 582: 578: 574: 570: 566: 562: 558: 548: 546: 541: 537: 533: 529: 525: 521: 516: 514: 511:(also termed 510: 506: 502: 498: 494: 490: 486: 482: 478: 474: 470: 467:)-HpETEs, 15( 466: 462: 458: 454: 450: 446: 441: 439: 435: 431: 427: 423: 419: 415: 411: 407: 403: 399: 395: 391: 390:hydroperoxide 387: 383: 379: 375: 371: 369: 363: 361: 355: 352:(also termed 351: 339: 333: 327: 320: 318: 315: 314: 293: 290: 286: 285: 280: 271: 270: 267: 260: 246: 245: 242: 235: 228: 224: 223: 221: 219: 216: 215: 208: 204: 203: 201: 195: 191: 190: 183: 179: 178: 176: 173: 169: 168: 164: 160: 157: 155: 153:ECHA InfoCard 150: 149: 142: 138: 137: 135: 133: 130: 129: 122: 118: 117: 115: 111: 106: 105: 98: 94: 93: 91: 88: 84: 83: 78: 73: 66: 60: 56: 52: 48: 44: 38: 34: 29: 25: 20: 8943:Cell biology 8909: 8854:Clinofibrate 8849:Ciprofibrate 8845: 8826: 8802:Antagonists: 8801: 8763: 8757:Troglitazone 8752:Tesaglitazar 8737:Sipoglitazar 8732:Saroglitazar 8707:Ragaglitazar 8694:Pioglitazone 8684:Pemaglitazar 8679:Peliglitazar 8664:Naveglitazar 8629:Lanifibranor 8624:Indeglitazar 8579:Edaglitazone 8574:Darglitazone 8554:Cevoglitazar 8492: 8457:Antagonists: 8456: 8430:Lanifibranor 8371: 8341:Antagonists: 8340: 8329:Troglitazone 8319:Tesaglitazar 8309:Saroglitazar 8304:Pioglitazone 8274:Muraglitazar 8246:Lanifibranor 8152: 8079: 8072: 8020: 7864:JNJ-26993135 7859:Fosinoprilat 7709: 7675: 7645:Caffeic acid 7570: 7537:Antagonists: 7536: 7507: 7364:Antagonists: 7363: 7334: 7278:Antagonists: 7277: 7231: 7120:Antagonists: 7119: 7088: 6966:stimulation: 6962: 6946:stimulation: 6942: 6917: 6891: 6868: 6850: 6801:vasodilation 6799: 6766: 6715: 6505:Leukotrienes 6471:Thromboxanes 6229:(1): 65–88. 6226: 6222: 6216: 6181: 6177: 6167: 6132: 6128: 6118: 6093: 6089: 6042: 6038: 6028: 5993: 5989: 5979: 5944: 5940: 5930: 5895: 5891: 5835: 5831: 5793: 5789: 5785: 5781: 5775: 5738: 5734: 5724: 5715: 5688: 5684: 5674: 5649: 5645: 5638: 5613: 5609: 5603: 5578: 5574: 5567: 5532: 5528: 5518: 5485: 5481: 5444: 5440: 5430: 5397: 5393: 5386: 5353: 5349: 5343: 5316: 5312: 5302: 5285: 5281: 5274: 5241: 5237: 5202: 5198: 5191: 5146: 5142: 5131: 5098: 5094: 5088: 5063: 5059: 5053: 5020: 5016: 5012: 5008: 4970: 4966: 4960: 4924: 4920: 4913: 4878: 4874: 4864: 4837: 4833: 4795: 4791: 4784: 4759: 4755: 4701: 4697: 4657: 4653: 4643: 4608: 4604: 4594: 4569: 4565: 4559: 4532: 4528: 4518: 4493: 4489: 4443: 4439: 4429: 4402: 4398: 4388: 4364:(1): 64–74. 4361: 4357: 4347: 4322: 4318: 4281: 4277: 4225: 4221: 4214: 4179: 4176:FEBS Journal 4175: 4165: 4130: 4126: 4116: 4079: 4075: 4068:Falck, J. R. 4061: 4026: 4022: 4012: 3998:cite journal 3966:(2): 69–79. 3963: 3959: 3924:(1): 80–89. 3921: 3917: 3910: 3865: 3861: 3851: 3826: 3822: 3816: 3783: 3779: 3741: 3737: 3681: 3677: 3637: 3633: 3627: 3590: 3586: 3543: 3539: 3501: 3497: 3439: 3435: 3395: 3391: 3385: 3350: 3346: 3336: 3311: 3307: 3301: 3277:(1): 55–62. 3274: 3270: 3260: 3238:(1): 87–97. 3235: 3231: 3221: 3207:(1): 51–60. 3204: 3200: 3193: 3168: 3164: 3158: 3131: 3127: 3121: 3117: 3113: 3109: 3105: 3097: 3062: 3056: 3019: 3015: 2957: 2953: 2915: 2911: 2905: 2878: 2874: 2864: 2837: 2833: 2823: 2780: 2777:FEBS Letters 2776: 2766: 2749: 2745: 2739: 2694: 2690: 2680: 2645: 2641: 2591: 2587: 2549: 2545: 2466: 2454: 2400: 2398: 2392: 2356:nucleophiles 2352:electrophile 2292: 2282: 2278: 2274: 2270: 2266: 2262: 2258: 2254: 2250: 2246: 2242: 2240: 2234: 2222: 2218: 2214: 2210: 2206: 2202: 2200: 2195: 2191: 2179: 2175: 2171: 2167: 2165: 2160: 2156: 2152: 2148: 2124: 2116: 2112: 2110: 2101: 2069: 2053: 2049: 2047: 2042: 2038: 2034: 2032: 2026: 2022: 2008: 2004: 2000: 1996: 1992: 1988: 1984: 1976: 1972: 1968: 1964: 1960: 1956: 1952: 1932: 1928: 1921: 1917: 1909: 1907: 1901: 1897: 1893: 1886: 1882: 1878: 1870: 1868: 1854: 1850: 1846: 1842: 1838: 1834: 1830: 1826: 1822: 1818: 1814: 1810: 1806: 1802: 1798: 1794: 1790: 1786: 1782: 1778: 1774: 1770: 1766: 1758: 1754: 1750: 1746: 1742: 1738: 1734: 1715: 1711: 1707: 1703: 1684: 1680: 1676: 1672: 1668: 1664: 1656: 1652: 1629: 1627: 1619: 1611: 1610:4-hydroxy-2( 1591: 1587: 1583: 1579: 1575: 1574:-hydroxy-14( 1571: 1568:hepoxilin A3 1525: 1521: 1517: 1511: 1507: 1499: 1495: 1491: 1487: 1483: 1479: 1475: 1471: 1467: 1463: 1449: 1445: 1441: 1437: 1433: 1429: 1421: 1417: 1413: 1409: 1405: 1401: 1397: 1386: 1379: 1371: 1367: 1363: 1359: 1355: 1351: 1347: 1343: 1339: 1335: 1331: 1327: 1316: 1308: 1304: 1257: 1233: 1229: 1225: 1221: 1217: 1213: 1197: 1193: 1189: 1185: 1181: 1174: 1170: 1167:diglycerides 1158: 1154: 1150: 1146: 1136: 1132: 1090: 1082: 1080: 1071: 1068: 1058: 1046: 1042: 1038: 1034: 1030: 1026: 1023:autoxidation 1019:Autoxidation 1018: 1017: 1012: 1008: 1004: 992: 991: 986: 982: 974: 970: 966: 950: 949: 940: 936: 932: 916: 912: 904: 903: 894: 890: 886: 882: 878: 874: 866: 862: 858: 854: 850: 846: 842: 841:), (i.e. 12( 836: 830: 826: 822: 818: 814: 810: 806: 802: 798: 794: 790: 786: 782: 778: 774: 770: 766: 762: 758: 754: 750: 742: 741: 724: 720: 716: 712: 706: 696: 692: 688: 684: 680: 676: 672: 668: 664: 660: 656: 652: 648: 644: 632: 628: 624: 620: 616: 612: 608: 600: 584: 580: 576: 572: 568: 564: 556: 554: 545:inflammatory 540:inflammatory 523: 519: 517: 513:epi-lipoxins 504: 500: 496: 492: 488: 484: 476: 472: 468: 464: 456: 455:)-HpETE, 15( 452: 449:stereoisomer 442: 437: 433: 417: 413: 409: 405: 401: 397: 393: 385: 381: 367: 365: 359: 357: 353: 349: 348: 80:Identifiers 71: 68:Other names 58: 54: 50: 46: 42: 8938:Eicosanoids 8933:Fatty acids 8884:Ronifibrate 8874:Farglitazar 8864:Englitazone 8747:Telmisartan 8674:Oxeglitazar 8619:Imiglitazar 8599:Farglitazar 8589:Englitazone 8584:Efatutazone 8564:Ciglitazone 8559:Chiglitazar 8549:Cannabidiol 8544:Bezafibrate 8524:Aleglitazar 8400:Elafibranor 8390:Bezafibrate 8289:Pemafibrate 8236:Gemfibrozil 8226:Fenofibrate 8216:Elafibranor 8186:Chiglitazar 8181:Bezafibrate 8166:Aleglitazar 8021:Precursors: 7844:Acebilustat 7718:inhibitors: 7688:Minocycline 7477:Zafirlukast 7422:Montelukast 7028:Leukotriene 6985:(Dinoprost) 6709:By function 6700:Virodhamine 6431:(Dinoprost) 6332:Prostanoids 6308:Eicosanoids 5838:: 144–153. 3108:)-hydroxy-5 2834:J Biol Chem 2552:(1): 1–10. 2513:Epi-lipoxin 2421:eosinophils 2325:to release 2257:)-HETE, 15( 1837:)-hydroxy-6 1661:glutathione 1392:. 14,15-HXA 1254:glutathione 1220:)-hydroxy-5 1101:-1 and -2, 817:)-hydroxy-5 641:double bond 639:about each 611:)-hydroxy-5 567:)-hydroxy-5 547:disorders. 522:)-HETE, 15( 507:) class of 282:Properties 159:100.214.805 8948:Immunology 8927:Categories 8894:Simfibrate 8869:Etofibrate 8859:Clofibride 8712:Reglitazar 8440:Seladelpar 8405:Fonadelpar 8210:prasterone 8191:Clofibrate 8132:modulators 7996:Cilastatin 7933:Azelastine 7698:Timegadine 7670:Hyperforin 7601:inhibitors 7467:Tomelukast 7462:Tipelukast 7447:SKF-104353 7442:Ritolukast 7437:Pranlukast 7432:Pobilukast 7412:Masilukast 7397:ICI-198615 7387:Cinalukast 7196:Ticolubant 7166:Moxilubant 7141:CGS-25019C 7034:modulators 6893:leukocytes 6672:Nonclassic 5947:: 79–105. 2529:References 2425:MDA-MB-231 2417:leukocytes 2373:chemotaxis 2348:hepoxilins 2289:15-Oxo-ETE 2141:A549 cells 2106:angiogenic 2078:fibroblast 2016:Activities 1904:)-nonenal. 1460:Isomerized 1376:hepoxilins 1362:)-epoxy-5( 1338:)-epoxy-5( 1131:. The 15( 1095:peroxidase 703:Production 699:)-HpETE). 605:enantiomer 424:viz., the 374:eicosanoid 317:Molar mass 227:44JHK6G39Q 172:IUPHAR/BPS 132:ChemSpider 108:3D model ( 97:54845-95-3 87:CAS Number 8846:Agonists: 8820:T-0070907 8644:LG-101506 8639:LG-100754 8634:LG-100268 8614:Ibuprofen 8604:Genistein 8539:Berberine 8496:5-Oxo-ETE 8493:Agonists: 8435:LG-101506 8425:L-165,041 8420:GW-501516 8410:Genistein 8372:Agonists: 8264:LG-100754 8259:LG-101506 8231:Genistein 8196:CP-775146 8153:Agonists: 7874:SC-57461A 7849:Captopril 7817:PD-146176 7774:Baicalein 7665:Fenleuton 7630:Baicalein 7571:Agonists: 7508:Agonists: 7472:Verlukast 7407:LY-170680 7402:Iralukast 7392:FPL-55712 7335:Agonists: 7291:ZK-158252 7286:LY-255283 7281:CP-195543 7232:Agonists: 7206:ZK-158252 7186:SB-209247 7161:LY-293111 7151:CP-195543 7146:CP-105696 7131:Amelubant 7113:LY-255283 7089:Agonists: 7031:signaling 6852:platelets 6608:Precursor 6514:Precursor 6350:Precursor 6315:Precursor 5101:: 84–91. 2399:5-Oxo-15( 2391:5-Oxo-15( 2377:monocytes 2188:apoptosis 2074:3T3 cells 2066:apoptosis 1983:(i.e., 5( 1765:(i.e., 5( 1729:(LX), LXA 1622:)-nonenal 1614:)-nonenal 1582:)-epoxy-5 1560:epidermis 1422:14,15-HXA 1387:14,15-HXB 1380:14,15-HXA 1252:contains 989:)-HpETE. 635:give the 593:chirality 532:autocrine 445:platelets 8906:See also 8827:Unknown: 8594:Etalocib 8569:Daidzein 8519:15-HpETE 8470:GSK-3787 8465:GSK-0660 8395:Daidzein 8380:15-HpETE 8334:WY-14643 8221:Etomoxir 8201:Daidzein 8161:15-HpETE 8069:See also 7965:Acivicin 7812:Luteolin 7731:BAYx1005 7703:Zileuton 7660:Curcumin 7655:CJ-13610 7545:BAYu9916 7540:BAYu9773 7457:Sulukast 7427:ONO-1078 7382:BAYx7195 7377:BAYu9916 7372:BAYu9773 7367:Ablukast 7255:15-HpETE 7245:12-HpETE 7191:SC-53228 7181:RP-69698 7176:RG-14893 7171:ONO-4057 7156:Etalocib 7042:Receptor 6895:: induce 6854:: induce 6680:Lipoxins 6251:20192361 6243:26560362 6208:35264541 6159:23499393 6110:16154383 6071:23945567 6020:19535459 5971:24161076 5922:24924423 5870:25450232 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15-Hydroxyeicosatetraenoic acid

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