1045:), human tumor cell growth, and human tumor metastasis in animal models implanted with certain types of human cancer cells. The possible beneficial effects of omega-3 fatty acid-rich diets in pathological states involving inflammation, hypertension, blood clotting, heart attacks and other cardiac diseases, strokes, brain seizures, pain perception, acute kidney injury, and cancer are suggested to result, at least in part, from the conversion of dietary EPA and DHA to EEQs and EPAs, respectively, and the cited subsequent actions of these metabolites.
1029:
produced significant reductions in systolic blood pressure and increased peripheral arteriole blood flow and reactivity in patients at high to intermediate risk for cardiovascular events; an EPA/DHA-rich diet also reduced the risk while high serum levels of DHA and EPA were associated with a low risk of neovascular age-related macular degeneration. Since such diets lead to large increases in the serum and urine levels of EPAs, EEQs, and the dihydroxy metabolites of these epoxides but relatively little or no increases in EETs or
26:
902:). 5,6-EEQ isomers are generally either not formed or formed in undetectable amounts while 8,9-EEQ isomers are formed in relatively small amounts by the cited CYPs. The EET-forming CYP epoxygenases often metabolize EPA to EEQs (as well as DHA to EDPs) at rates that exceed their rates in metabolizing arachidonic acid to EETs; that is, EPA (and DHA) appear to be preferred over arachidonic acid as substrates for many CYP epoxygenases.
1000:(EETs). In comparison to the many activities attributed to the EETs in animal model studies, a limited set of studies indicate that EEQs (and EPAs) mimic EETs in their abilities to dilate arterioles, reduce hypertension, inhibit inflammation (the anti-inflammatory actions of EEQ are less potent than those of the EETs) and thereby reduce occlusion of arteries to protect the heart and prevent
797:(EDPs) isomers. In general, the same epoxygenases that accomplish these metabolic conversions also metabolize the omega-6 fatty acid, EPA, to 10 epoxide isomers, the EEQs. These epoxygenases fall into several subfamilies including the cytochrome P4501A (i.e.CYP1A), CYP2B, CYP2C, CYP2E, and CYP2J subfamilies, and within the CYP3A subfamily, CYP3A4. In humans,
941:
dihydroxyeicosatetraenoic acids (diHETEs). The omega-3 fatty acid epoxides, EEQs and EPAs, appear to be preferred over EETs as substates for sEH. sEH converts 17,18-EEQ isomers to 17,18-dihydroxy-eicosatrienoic acid isomers (17,18-diHETEs), 14,15-EEQ isomers to 14,15-diHETE isomers, 11,12-EEQ isomers
837:
metabolize EPA to EEQs, in most cases forming principally 17,18-EEQ with smaller amounts of 5,6-EEQ, 8,9-EEQ, 11,12-EEQ, and 14,15-EEQ isomers. However, CYP2C11, CYP2C18, and CYP2S1 also form 14,15-EEQ isomers while CYP2C19 also forms 11,12-EEQ isomers. The isomers formed by these CYPs vary greatly
1028:
properties in relieving certain types of pain. Often, the EEQs (and EPAs) exhibit greater potency and/or effectiveness than EET in these actions. In human studies potentially relevant to one or more of these activities, consumption of long chain omega-3 fatty acid (i.e. EPA- and DHA-rich) diet
921:
as well as endogenously-formed compounds; since many of these same compounds also induce increases in the levels of the epoxygenases, CYP oxygenase levels and consequently EEQ levels in humans vary widely and are highly dependent on recent consumption history; numerous other factors, including
1037:-producing metabolites of arachidonic acid, DHA, and/or EEQs, it is suggested that the diet-induced increases in EPAs and/or EEQs are responsible for this beneficial effects. In direct contrast to the EETs which have stimulating effects in the following activities (see
969:(mEH or epoxide hydrolase 2 ) can metabolize EEQs to their dihydroxy products but is regarded as not contributing significantly to EEQ inactivation in vivo except possibly in rare tissues where the sEH level is exceptionally low while the mEH level is high.
588:. These epoxygenases can metabolize EPA to as many as 10 epoxides that differ in the site and/or stereoisomer of the epoxide formed; however, the formed EEQs, while differing in potency, often have similar bioactivities and are commonly considered together.
917:. These tissues are known to metabolize arachidonic acid to EETs; it has been shown or is presumed that they also metabolize EPA to EEQs. Note, however, that the CYP epoxygenases, similar to essentially all CYP450 enzymes, are involved in the metabolism of
2014:
Merino J, Sala-Vila A, Kones R, Ferre R, Plana N, Girona J, Ibarretxe D, Heras M, Ros E, Masana L (2014). "Increasing long-chain n-3PUFA consumption improves small peripheral artery function in patients at intermediate-high cardiovascular risk".
1319:
Frömel T, Fleming I (2015). "Whatever happened to the epoxyeicosatrienoic Acid-like endothelium-derived hyperpolarizing factor? The identification of novel classes of lipid mediators and their role in vascular homeostasis".
1403:
Frömel T, Kohlstedt K, Popp R, Yin X, Awwad K, Barbosa-Sicard E, Thomas AC, Lieberz R, Mayr M, Fleming I (2013). "Cytochrome P4502S1: A novel monocyte/macrophage fatty acid epoxygenase in human atherosclerotic plaques".
1928:
Merle BM, Benlian P, Puche N, Bassols A, Delcourt C, Souied EH, Nutritional AMD Treatment II Study Group (2014). "Circulating omega-3 Fatty acids and neovascular age-related macular degeneration".
1362:
Westphal C, Konkel A, Schunck WH (2015). "Cytochrome P450 Enzymes in the
Bioactivation of Polyunsaturated Fatty Acids and Their Role in Cardiovascular Disease". In Hrycay EG, Bandiera SM (eds.).
638:-eicosapentaenoic acid. Certain cytochrome P450 epoxygenases metabolize EPA by converting one of these double bounds to an epoxide thereby forming one of 5 possible eicosatetraenoic acid epoxide
962:)-diHETE. Since the diHETE products are as a rule generally far less active than their epoxide precursors, the sEH pathway of EET metabolism is regarded as a critical EEQ-inactivating pathway.
385:)-EEQ: InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12-/t18-,19+/m1/s1
976:-like reaction. This pathway may serve to limit the action of EETs or store them for future release. EETs are also inactivated by being further metabolized through three other pathways:
367:)-EEQ: InChI=1S/C20H30O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,12-3-,13-10-
331:)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,12-9-,13-10-
313:)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h3-4,6-7,9-10,12-13,18-19H,2,5,8,11,14-17H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-
349:)-EEQ: InChI=1S/C20H30O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h3-4,6,8-10,12-13,18-19H,2,5,7,11,14-17H2,1H3,(H,21,22)/b4-3-,8-6-,12-9-,13-10-
1269:
Fer M, Dréano Y, Lucas D, Corcos L, Salaün JP, Berthou F, Amet Y (2008). "Metabolism of eicosapentaenoic and docosahexaenoic acids by recombinant human cytochromes P450".
95:
894:, which are classified as CYP monooxygenase rather than CYP epoxygeanses because they metabolize arachidonic acid to monohydroxy eicosatetraenoic acid products (see
1590:
Shahabi P, Siest G, Meyer UA, Visvikis-Siest S (2014). "Human cytochrome P450 epoxygenases: Variability in expression and role in inflammation-related disorders".
175:
159:
143:
127:
111:
942:
to 11,12-diHETE isomers, 8,9-EEQ isomers to 8,9-diHETE isomers, and 5,6-EEQ isomers to 5,6-diHETE isomers. The product diHETEs, like their epoxy precursors, are
898:), i.e. 19-hydroxyeicosatetraenoic acid and/or 20-hydroxyeicosatetranoic acid, take on epoxygease activity in converting EPA primarily to 17,18-EEQ isomers (see
1887:
Augood C, Chakravarthy U, Young I, Vioque J, De Jong PT, Bentham G, Rahu M, Seland J, Soubrane G, Tomazzoli L, Topouzis F, Vingerling JR, Fletcher AE (2008).
401:
1889:"Oily fish consumption, dietary docosahexaenoic acid and eicosapentaenoic acid intakes, and associations with neovascular age-related macular degeneration"
1963:
Fischer R, Konkel A, Mehling H, Blossey K, Gapelyuk A, Wessel N, von
Schacky C, Dechend R, Muller DN, Rothe M, Luft FC, Weylandt K, Schunck WH (2014).
1809:
Fleming I (2014). "The pharmacology of the cytochrome P450 epoxygenase/soluble epoxide hydrolase axis in the vasculature and cardiovascular disease".
1547:
Xu M, Ju W, Hao H, Wang G, Li P (2013). "Cytochrome P450 2J2: Distribution, function, regulation, genetic polymorphisms and clinical significance".
930:
In cells, EEQs are rapidly metabolized by the same enzyme that similarly metabolizes other epoxy fatty acids including the EETs viz., cytosolic
905:
The EEQ-forming cytochromes are widely distributed in the tissues of humans and other mammals, including blood vessel endothelium, blood vessel
606:
double bonds between carbons 5 and 6, 8 and 9, 11 and 12, 14 and 15, and 17 and 18; each of these double bonds is designated with the notation
1379:
296:
2184:
895:
2099:
Westphal C, Konkel A, Schunck WH (2011). "CYP-eicosanoids--a new link between omega-3 fatty acids and cardiac disease?".
546:
966:
1720:
Konkel A, Schunck WH (2011). "Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids".
2229:
794:
762:
2224:
931:
777:, which possess two double bonds, to 4 different epoxide isomers, i.e. two different 9,10-epoxide isomers termed
1038:
1005:
997:
899:
770:
1965:"Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway"
1449:"Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450"
601:
2219:
2214:
2204:
1852:
Fleming I (2016). "The factor in EDHF: Cytochrome P450 derived lipid mediators and vascular signaling".
615:
578:
2194:
2189:
985:
922:
individual genetic differences, also contribute to the variability in CYP450 epoxygenase expression.
790:
2136:"Ω-3 polyunsaturated fatty acids-derived lipid metabolites on angiogenesis, inflammation and cancer"
25:
2209:
935:
43:
1834:
1702:
1572:
1429:
786:
597:
574:
1677:
Bellien J, Joannides R (2013). "Epoxyeicosatrienoic acid pathway in human health and diseases".
1447:
Lucas D, Goulitquer S, Marienhagen J, Fer M, Dreano Y, Schwaneberg U, Amet Y, Corcos L (2010).
2199:
2161:
2116:
2081:
2032:
1996:
1945:
1910:
1869:
1826:
1788:
1737:
1694:
1659:
1607:
1564:
1529:
1480:
1421:
1385:
1375:
1337:
1286:
1248:
1194:
1145:
1093:
733:
of each epoxide. For example, they metabolize EPA at its 17,18 double bond to a mixture of 17
2151:
2143:
2108:
2071:
2063:
2024:
1986:
1976:
1937:
1900:
1861:
1818:
1778:
1768:
1729:
1686:
1649:
1641:
1599:
1556:
1519:
1511:
1470:
1460:
1413:
1367:
1329:
1278:
1238:
1230:
1184:
1176:
1135:
1127:
1083:
1073:
766:
497:
62:
1120:"The role of long chain fatty acids and their epoxide metabolites in nociceptive signaling"
1165:"Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer"
981:
582:
2147:
2112:
2067:
1131:
236:
220:
204:
259:
252:
2156:
2135:
2076:
2051:
1991:
1964:
1783:
1756:
1654:
1629:
1524:
1499:
1475:
1448:
1364:
Monooxygenase, Peroxidase and
Peroxygenase Properties and Mechanisms of Cytochrome P450
1243:
1218:
1189:
1164:
1140:
1119:
1088:
1065:
1034:
977:
778:
540:
2178:
1603:
782:
774:
283:
1838:
1706:
1576:
1433:
1042:
1030:
769:, which possess four double bonds, to 8 different epoxide isomers which are termed
2028:
1180:
1733:
1690:
1560:
1366:. Advances in Experimental Medicine and Biology. Vol. 851. pp. 151–87.
1234:
1371:
639:
585:
1645:
1078:
1865:
1417:
1282:
1219:"Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism"
1113:
1111:
1109:
1107:
972:
In addition to the sEH pathway, EETs may be acylated into phospholipids in an
943:
918:
914:
730:
525:
1905:
1888:
1025:
973:
2165:
2120:
2085:
2036:
2000:
1949:
1914:
1873:
1830:
1792:
1741:
1698:
1663:
1611:
1568:
1533:
1484:
1425:
1389:
1341:
1290:
1252:
1198:
1149:
1097:
2134:
Wang W, Zhu J, Lyu F, Panigrahy D, Ferrara KW, Hammock B, Zhang G (2014).
1941:
1822:
1773:
1333:
1223:
Biochimica et
Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids
910:
906:
570:
1981:
1465:
765:
to epoxide-containing products. They metabolize the omega-6 fatty acids
879:
871:
818:
814:
270:
1515:
1804:
1802:
1001:
891:
887:
883:
875:
834:
830:
826:
822:
810:
806:
802:
798:
750:
1630:"Soluble epoxide hydrolase: Gene structure, expression and deletion"
1500:"The role of epoxyeicosatrienoic acids in the cardiovascular system"
1498:
Yang L, Mäki-Petäjä K, Cheriyan J, McEniery C, Wilkinson IB (2015).
539:
Except where otherwise noted, data are given for materials in their
946:
mixtures; for instance, sEH converts 17,18-EEQ to a mixture of 17(
909:
plaques, heart muscle, kidneys, pancreas, intestine, lung, brain,
186:
174:
158:
142:
126:
110:
94:
75:
2050:
Iliff JJ, Jia J, Nelson J, Goyagi T, Klaus J, Alkayed NJ (2010).
996:
EEQs, similar to EDPs, have not be studied nearly as well as the
838:
with, for example, the 17,18-EEQs made by CYP1A2 consisting of 17
938:
781:
or leukotoxins and two different 12,13-epoxides isomers termed
1722:
Biochimica et
Biophysica Acta (BBA) - Proteins and Proteomics
1314:
1312:
1310:
1308:
1306:
1304:
1302:
1300:
1041:), EEQs (and EPAs) inhibit new blood vessel formation (i.e.
934:(also termed sEH or the EPHX2), to form their corresponding
722:-eicosatetraenoic acid). The epoxydases typically make both
1264:
1262:
1212:
1210:
1208:
749:-EEQ. The EEQ products therefore consist of as many as ten
854:-EEQ and those made by CYP2D6 consisting principally of 17
706:-eicosatetraenoic acid), and 17,18-EEQ (i.e. 17,18-epoxy-5
761:
Cellular cytochrome P450 epoxygenases metabolize various
1757:"Anti-inflammatory effects of epoxyeicosatrienoic acids"
793:, which possesses six double bonds, to twelve different
2052:"Epoxyeicosanoid signaling in CNS function and disease"
1066:"Arachidonic acid cytochrome P450 epoxygenase pathway"
690:-eicosatetraenoic acid), 14,15-EEQ (i.e. 14,15-epoxy-5
674:-eicosatetraenoic acid), 11,12-EEQ (i.e. 11,12-epoxy-5
1006:
Epoxyeicosatrienoic acid § Clinical significance
417:)-EEQ: CC/C=C\C/C=C\C/C=C\C/C=C\CC1(O1)CCCC(=O)O
642:. These regioisomers are: 5,6-EEQ (i.e. 5,6-epoxy-8
482:)-EEQ: CCC1O1C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
469:)-EEQ: CC/C=C\CC1O1C/C=C\C/C=C\C/C=C\CCCC(=O)O
456:)-EEQ: CC/C=C\C/C=C\CC1O1C/C=C\C/C=C\CCCC(=O)O
443:)-EEQ: CC/C=C\C/C=C\C/C=C\CC1O1C/C=C\CCCC(=O)O
430:)-EEQ: CC/C=C\C/C=C\C/C=C\C/C=C\CC1O1CCCC(=O)O
1024:Inflammation); they also mimic EETs in possessing
658:-eicosatetraenoic acid), 8,9-EEQ (i.e. 8,9-epoxy-5
1118:Wagner K, Vito S, Inceoglu B, Hammock BD (2014).
573:that various cell types make by metabolizing the
1930:Investigative Ophthalmology & Visual Science
61:
1755:Thomson SJ, Askari A, Bishop-Bailey D (2012).
8:
1623:
1621:
1357:
1355:
1353:
1351:
1059:
1057:
2140:Prostaglandins & Other Lipid Mediators
2101:Prostaglandins & Other Lipid Mediators
2056:Prostaglandins & Other Lipid Mediators
1893:The American Journal of Clinical Nutrition
1761:International Journal of Vascular Medicine
1124:Prostaglandins & Other Lipid Mediators
17:
2155:
2075:
1990:
1980:
1904:
1782:
1772:
1653:
1523:
1474:
1464:
1242:
1188:
1139:
1087:
1077:
1504:British Journal of Clinical Pharmacology
984:, and elongation by enzymes involved in
2017:The Journal of Nutritional Biochemistry
1271:Archives of Biochemistry and Biophysics
1053:
870:-EEQ. In addition to the cited CYP's,
785:or isoleukotoxins. They metabolize the
406:
301:
1679:Journal of Cardiovascular Pharmacology
1163:Zhang G, Kodani S, Hammock BD (2014).
1039:Epoxyeicosatrienoic acid § Cancer
388:Key: GPQVVJQEBXAKBJ-YQLHGUCYSA-N
370:Key: RGZIXZYRGZWDMI-QXBXTPPVSA-N
352:Key: QHOKDYBJJBDJGY-BVILWSOJSA-N
334:Key: YKIOHMXLFWMWKD-JJUYGIQRSA-N
316:Key: AKBOADNSBQNXRS-LTKCOYKYSA-N
251:
235:
219:
203:
7:
2148:10.1016/j.prostaglandins.2014.07.002
2113:10.1016/j.prostaglandins.2011.09.001
2068:10.1016/j.prostaglandins.2009.06.004
1132:10.1016/j.prostaglandins.2014.09.001
569:s) are a set of biologically active
862:-EEQ with far smaller amounts of 17
596:EPA is a straight-chain, 20 carbon
273:
1322:Antioxidants & Redox Signaling
14:
1604:10.1016/j.pharmthera.2014.05.011
509:
24:
1592:Pharmacology & Therapeutics
896:20-Hydroxyeicosatetraenoic acid
543:(at 25 °C , 100 kPa).
1628:Harris TR, Hammock BD (2013).
1012:Regulation of blood pressure,
515:
503:
1:
2029:10.1016/j.jnutbio.2014.02.004
1969:The Journal of Lipid Research
1453:The Journal of Lipid Research
1181:10.1016/j.plipres.2013.11.003
1070:The Journal of Lipid Research
618:used here. EPA is therefore 5
1734:10.1016/j.bbapap.2010.09.009
1691:10.1097/FJC.0b013e318273b007
1561:10.3109/03602532.2013.806537
1406:Basic Research in Cardiology
1235:10.1016/j.bbalip.2014.07.020
967:microsomal epoxide hydrolase
1372:10.1007/978-3-319-16009-2_6
1217:Spector AA, Kim HY (2015).
1072:. 50 Suppl (Suppl): S52–6.
763:polyunsaturated fatty acids
614:configuration in the IUPAC
19:Epoxyeicosatetraenoic acid
2246:
1646:10.1016/j.gene.2013.05.008
1169:Progress in Lipid Research
1079:10.1194/jlr.R800038-JLR200
1020:Strokes and seizures, and
795:epoxydocosapentaenoic acid
559:Epoxyeicosatetraenoic acid
1866:10.1016/j.vph.2016.03.001
1418:10.1007/s00395-012-0319-8
1283:10.1016/j.abb.2008.01.002
998:epoxyeicosatrienoic acids
932:soluble epoxide hydrolase
846:-EEQ but no detectable 17
771:epoxyeicosatrienoic acids
537:
490:
397:
292:
36:
23:
900:Epoxyeicosatrienoic acid
2185:Metabolic intermediates
1811:Pharmacological Reviews
1549:Drug Metabolism Reviews
1942:10.1167/iovs.14-13916
1906:10.1093/ajcn/88.2.398
1854:Vascular Pharmacology
1823:10.1124/pr.113.007781
1334:10.1089/ars.2014.6150
992:Clinical significance
616:Chemical nomenclature
579:eicosapentaenoic acid
986:fatty acid synthesis
791:docosahexaenoic acid
581:(EPA), with certain
1982:10.1194/jlr.M047357
1774:10.1155/2012/605101
1466:10.1194/jlr.M003061
1064:Spector AA (2009).
533: g·mol
20:
2142:. 113–115: 13–20.
787:omega-3 fatty acid
598:omega-3 fatty acid
575:omega 3 fatty acid
547:Infobox references
18:
2230:Animal physiology
1516:10.1111/bcp.12603
1381:978-3-319-16008-5
1126:. 113–115: 2–12.
954:)-diHETE and 17(
555:Chemical compound
553:
552:
282:17(S),18(S)-EEQ:
176:Interactive image
160:Interactive image
144:Interactive image
128:Interactive image
112:Interactive image
96:Interactive image
2237:
2225:Human physiology
2170:
2169:
2159:
2131:
2125:
2124:
2096:
2090:
2089:
2079:
2047:
2041:
2040:
2011:
2005:
2004:
1994:
1984:
1975:(6): 1150–1164.
1960:
1954:
1953:
1925:
1919:
1918:
1908:
1884:
1878:
1877:
1849:
1843:
1842:
1806:
1797:
1796:
1786:
1776:
1752:
1746:
1745:
1717:
1711:
1710:
1674:
1668:
1667:
1657:
1625:
1616:
1615:
1587:
1581:
1580:
1544:
1538:
1537:
1527:
1495:
1489:
1488:
1478:
1468:
1444:
1438:
1437:
1400:
1394:
1393:
1359:
1346:
1345:
1316:
1295:
1294:
1266:
1257:
1256:
1246:
1214:
1203:
1202:
1192:
1160:
1154:
1153:
1143:
1115:
1102:
1101:
1091:
1081:
1061:
767:arachidonic acid
610:to indicate its
532:
517:
511:
505:
498:Chemical formula
275:
255:
239:
223:
207:
178:
162:
146:
130:
114:
98:
65:
28:
21:
2245:
2244:
2240:
2239:
2238:
2236:
2235:
2234:
2175:
2174:
2173:
2133:
2132:
2128:
2107:(1–4): 99–108.
2098:
2097:
2093:
2049:
2048:
2044:
2013:
2012:
2008:
1962:
1961:
1957:
1927:
1926:
1922:
1886:
1885:
1881:
1851:
1850:
1846:
1808:
1807:
1800:
1754:
1753:
1749:
1719:
1718:
1714:
1676:
1675:
1671:
1627:
1626:
1619:
1589:
1588:
1584:
1546:
1545:
1541:
1497:
1496:
1492:
1446:
1445:
1441:
1402:
1401:
1397:
1382:
1361:
1360:
1349:
1328:(14): 1273–92.
1318:
1317:
1298:
1268:
1267:
1260:
1216:
1215:
1206:
1162:
1161:
1157:
1117:
1116:
1105:
1063:
1062:
1055:
1051:
1016:Heart disease,
994:
982:omega oxidation
965:Membrane-bound
928:
779:coronaric acids
759:
594:
583:cytochrome P450
556:
549:
544:
530:
520:
514:
508:
500:
486:
483:
470:
457:
444:
431:
418:
405:
404:
393:
390:
389:
386:
372:
371:
368:
354:
353:
350:
336:
335:
332:
318:
317:
314:
300:
299:
288:
276:
264:
181:
79:
68:
46:
32:
29:
12:
11:
5:
2243:
2241:
2233:
2232:
2227:
2222:
2220:Blood pressure
2217:
2212:
2207:
2202:
2197:
2192:
2187:
2177:
2176:
2172:
2171:
2126:
2091:
2062:(3–4): 68–84.
2042:
2006:
1955:
1920:
1899:(2): 398–406.
1879:
1844:
1817:(4): 1106–40.
1798:
1747:
1712:
1669:
1617:
1582:
1539:
1490:
1459:(5): 1125–33.
1439:
1395:
1380:
1347:
1296:
1258:
1204:
1155:
1103:
1052:
1050:
1047:
1035:cyclooxygenase
993:
990:
978:beta oxidation
927:
926:EEQ metabolism
924:
783:vernolic acids
758:
755:
593:
590:
554:
551:
550:
545:
541:standard state
538:
535:
534:
528:
522:
521:
518:
512:
506:
501:
496:
493:
492:
488:
487:
485:
484:
473:
471:
460:
458:
447:
445:
434:
432:
421:
419:
408:
400:
399:
398:
395:
394:
392:
391:
387:
376:
375:
373:
369:
358:
357:
355:
351:
340:
339:
337:
333:
322:
321:
319:
315:
304:
303:
295:
294:
293:
290:
289:
287:
286:
279:
277:
269:
266:
265:
263:
262:
256:
240:
224:
208:
191:
189:
183:
182:
180:
179:
163:
147:
131:
115:
99:
82:
80:
73:
70:
69:
67:
66:
49:
47:
42:
39:
38:
34:
33:
30:
13:
10:
9:
6:
4:
3:
2:
2242:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2215:Inflammations
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2182:
2180:
2167:
2163:
2158:
2153:
2149:
2145:
2141:
2137:
2130:
2127:
2122:
2118:
2114:
2110:
2106:
2102:
2095:
2092:
2087:
2083:
2078:
2073:
2069:
2065:
2061:
2057:
2053:
2046:
2043:
2038:
2034:
2030:
2026:
2022:
2018:
2010:
2007:
2002:
1998:
1993:
1988:
1983:
1978:
1974:
1970:
1966:
1959:
1956:
1951:
1947:
1943:
1939:
1936:(3): 2010–9.
1935:
1931:
1924:
1921:
1916:
1912:
1907:
1902:
1898:
1894:
1890:
1883:
1880:
1875:
1871:
1867:
1863:
1859:
1855:
1848:
1845:
1840:
1836:
1832:
1828:
1824:
1820:
1816:
1812:
1805:
1803:
1799:
1794:
1790:
1785:
1780:
1775:
1770:
1766:
1762:
1758:
1751:
1748:
1743:
1739:
1735:
1731:
1728:(1): 210–22.
1727:
1723:
1716:
1713:
1708:
1704:
1700:
1696:
1692:
1688:
1685:(3): 188–96.
1684:
1680:
1673:
1670:
1665:
1661:
1656:
1651:
1647:
1643:
1639:
1635:
1631:
1624:
1622:
1618:
1613:
1609:
1605:
1601:
1598:(2): 134–61.
1597:
1593:
1586:
1583:
1578:
1574:
1570:
1566:
1562:
1558:
1555:(3): 311–52.
1554:
1550:
1543:
1540:
1535:
1531:
1526:
1521:
1517:
1513:
1509:
1505:
1501:
1494:
1491:
1486:
1482:
1477:
1472:
1467:
1462:
1458:
1454:
1450:
1443:
1440:
1435:
1431:
1427:
1423:
1419:
1415:
1411:
1407:
1399:
1396:
1391:
1387:
1383:
1377:
1373:
1369:
1365:
1358:
1356:
1354:
1352:
1348:
1343:
1339:
1335:
1331:
1327:
1323:
1315:
1313:
1311:
1309:
1307:
1305:
1303:
1301:
1297:
1292:
1288:
1284:
1280:
1277:(2): 116–25.
1276:
1272:
1265:
1263:
1259:
1254:
1250:
1245:
1240:
1236:
1232:
1229:(4): 356–65.
1228:
1224:
1220:
1213:
1211:
1209:
1205:
1200:
1196:
1191:
1186:
1182:
1178:
1174:
1170:
1166:
1159:
1156:
1151:
1147:
1142:
1137:
1133:
1129:
1125:
1121:
1114:
1112:
1110:
1108:
1104:
1099:
1095:
1090:
1085:
1080:
1075:
1071:
1067:
1060:
1058:
1054:
1048:
1046:
1044:
1040:
1036:
1032:
1027:
1023:
1019:
1015:
1011:
1007:
1003:
999:
991:
989:
987:
983:
979:
975:
970:
968:
963:
961:
957:
953:
949:
945:
940:
937:
933:
925:
923:
920:
916:
912:
908:
903:
901:
897:
893:
889:
885:
881:
877:
873:
869:
865:
861:
857:
853:
849:
845:
841:
836:
832:
828:
824:
820:
816:
812:
808:
804:
800:
796:
792:
788:
784:
780:
776:
775:linoleic acid
772:
768:
764:
756:
754:
752:
748:
744:
740:
736:
732:
729:
725:
721:
717:
713:
709:
705:
701:
697:
693:
689:
685:
681:
677:
673:
669:
665:
661:
657:
653:
649:
645:
641:
637:
633:
629:
625:
621:
617:
613:
609:
605:
604:
599:
591:
589:
587:
584:
580:
576:
572:
568:
564:
560:
548:
542:
536:
529:
527:
524:
523:
502:
499:
495:
494:
489:
481:
477:
472:
468:
464:
459:
455:
451:
446:
442:
438:
433:
429:
425:
420:
416:
412:
407:
403:
396:
384:
380:
374:
366:
362:
356:
348:
344:
338:
330:
326:
320:
312:
308:
302:
298:
291:
285:
281:
280:
278:
272:
268:
267:
261:
257:
254:
249:
245:
241:
238:
233:
229:
225:
222:
217:
213:
209:
206:
201:
197:
193:
192:
190:
188:
185:
184:
177:
172:
168:
164:
161:
156:
152:
148:
145:
140:
136:
132:
129:
124:
120:
116:
113:
108:
104:
100:
97:
92:
88:
84:
83:
81:
77:
72:
71:
64:
59:
55:
51:
50:
48:
45:
41:
40:
35:
27:
22:
16:
2205:Cell biology
2139:
2129:
2104:
2100:
2094:
2059:
2055:
2045:
2023:(6): 642–6.
2020:
2016:
2009:
1972:
1968:
1958:
1933:
1929:
1923:
1896:
1892:
1882:
1857:
1853:
1847:
1814:
1810:
1764:
1760:
1750:
1725:
1721:
1715:
1682:
1678:
1672:
1640:(2): 61–74.
1637:
1633:
1595:
1591:
1585:
1552:
1548:
1542:
1510:(1): 28–44.
1507:
1503:
1493:
1456:
1452:
1442:
1409:
1405:
1398:
1363:
1325:
1321:
1274:
1270:
1226:
1222:
1172:
1168:
1158:
1123:
1069:
1043:angiogenesis
1031:lipoxygenase
1021:
1017:
1013:
1009:
1008:sections on
995:
971:
964:
959:
955:
951:
947:
929:
904:
867:
863:
859:
855:
851:
847:
843:
839:
773:or EETs and
760:
746:
742:
738:
734:
727:
723:
719:
715:
711:
707:
703:
699:
695:
691:
687:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
643:
640:regioisomers
635:
631:
627:
623:
619:
611:
607:
602:
595:
586:epoxygenases
566:
562:
558:
557:
479:
475:
466:
462:
453:
449:
440:
436:
427:
423:
414:
410:
382:
378:
364:
360:
346:
342:
328:
324:
310:
306:
250:)-EEQ:
247:
243:
237:CHEBI:137269
234:)-EEQ:
231:
227:
221:CHEBI:137267
218:)-EEQ:
215:
211:
205:CHEBI:137193
202:)-EEQ:
199:
195:
173:)-EEQ:
170:
166:
157:)-EEQ:
154:
150:
141:)-EEQ:
138:
134:
125:)-EEQ:
122:
118:
109:)-EEQ:
106:
102:
93:)-EEQ:
90:
86:
60:)-EEQ:
57:
53:
37:Identifiers
15:
2195:Fatty acids
2190:Docosanoids
919:xenobiotics
915:macrophages
741:-EEQ and 17
731:enantiomers
600:containing
491:Properties
260:CHEBI:72852
253:CHEBI:76955
63:131339-23-6
2210:Immunology
2179:Categories
1767:: 605101.
1412:(1): 319.
1175:: 108–23.
1049:References
944:enantiomer
757:Production
526:Molar mass
74:3D model (
44:CAS Number
1860:: 31–40.
1026:analgesia
974:acylation
911:monocytes
592:Structure
258:generic:
31:17,18-EEQ
2200:Epoxides
2166:25019221
2121:21945326
2086:19545642
2037:24746829
2001:24634501
1950:24557349
1915:18689376
1874:26975734
1839:39465144
1831:25244930
1793:22848834
1742:20869469
1707:42452896
1699:23011468
1664:23701967
1612:24882266
1577:22721300
1569:23865864
1534:25655310
1485:19965576
1426:23224081
1390:26002735
1342:25330284
1291:18206980
1253:25093613
1199:24345640
1150:25240260
1098:18952572
907:atheroma
571:epoxides
284:16061089
2157:4306447
2077:2844927
1992:4031946
1784:3405717
1655:3733540
1525:4500322
1476:2853439
1434:9158244
1244:4314516
1190:3914417
1141:4254344
1089:2674692
1002:strokes
936:vicinal
880:CYP4F12
872:CYP4A11
819:CYP2C19
815:CYP2C18
751:isomers
531:318.457
271:PubChem
2164:
2154:
2119:
2084:
2074:
2035:
1999:
1989:
1948:
1913:
1872:
1837:
1829:
1791:
1781:
1740:
1705:
1697:
1662:
1652:
1610:
1575:
1567:
1532:
1522:
1483:
1473:
1432:
1424:
1388:
1378:
1340:
1289:
1251:
1241:
1197:
1187:
1148:
1138:
1096:
1086:
913:, and
892:CYP2E1
890:, and
888:CYP1A2
884:CYP1A1
876:CYP4F8
835:CYP2S1
833:, and
831:CYP3A4
827:CYP2J2
823:CYP2E1
811:CYP2C9
807:CYP2C8
803:CYP1A2
799:CYP1A1
402:SMILES
1835:S2CID
1703:S2CID
1573:S2CID
1430:S2CID
1004:(see
958:),18(
950:),19(
567:EpETE
565:s or
478:),18(
465:),15(
452:),12(
381:),18(
363:),15(
345:),12(
297:InChI
246:),18(
230:),15(
214:),12(
187:ChEBI
169:),18(
153:),15(
137:),12(
76:JSmol
56:),18(
2162:PMID
2117:PMID
2082:PMID
2033:PMID
1997:PMID
1946:PMID
1911:PMID
1870:PMID
1827:PMID
1789:PMID
1765:2012
1738:PMID
1726:1814
1695:PMID
1660:PMID
1634:Gene
1608:PMID
1565:PMID
1530:PMID
1481:PMID
1422:PMID
1386:PMID
1376:ISBN
1338:PMID
1287:PMID
1249:PMID
1227:1851
1195:PMID
1146:PMID
1094:PMID
939:diol
439:),9(
426:),6(
413:),6(
327:),9(
309:),6(
198:),9(
121:),9(
105:),6(
89:),6(
2152:PMC
2144:doi
2109:doi
2072:PMC
2064:doi
2025:doi
1987:PMC
1977:doi
1938:doi
1901:doi
1862:doi
1819:doi
1779:PMC
1769:doi
1730:doi
1687:doi
1650:PMC
1642:doi
1638:526
1600:doi
1596:144
1557:doi
1520:PMC
1512:doi
1471:PMC
1461:doi
1414:doi
1410:108
1368:doi
1330:doi
1279:doi
1275:471
1239:PMC
1231:doi
1185:PMC
1177:doi
1136:PMC
1128:doi
1084:PMC
1074:doi
866:,18
858:,18
850:,18
842:,18
745:,18
737:,18
718:,14
714:,11
702:,17
698:,11
686:,17
682:,14
670:,17
666:,14
662:,11
654:,17
650:,14
646:,11
634:,17
630:,14
626:,11
612:cis
603:cis
563:EEQ
561:s (
474:17(
461:14(
448:11(
377:17(
359:14(
341:11(
274:CID
242:17(
226:14(
210:11(
165:17(
149:14(
133:11(
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2181::
2160:.
2150:.
2138:.
2115:.
2105:96
2103:.
2080:.
2070:.
2060:91
2058:.
2054:.
2031:.
2021:25
2019:.
1995:.
1985:.
1973:55
1971:.
1967:.
1944:.
1934:55
1932:.
1909:.
1897:88
1895:.
1891:.
1868:.
1858:86
1856:.
1833:.
1825:.
1815:66
1813:.
1801:^
1787:.
1777:.
1763:.
1759:.
1736:.
1724:.
1701:.
1693:.
1683:61
1681:.
1658:.
1648:.
1636:.
1632:.
1620:^
1606:.
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1528:.
1518:.
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1479:.
1469:.
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1420:.
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1336:.
1326:22
1324:.
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1285:.
1273:.
1261:^
1247:.
1237:.
1225:.
1221:.
1207:^
1193:.
1183:.
1173:53
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1167:.
1144:.
1134:.
1122:.
1106:^
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1068:.
1056:^
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980:,
886:,
882:,
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874:,
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825:,
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805:,
801:,
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753:.
710:,8
694:,8
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2123:.
2111::
2088:.
2066::
2039:.
2027::
2003:.
1979::
1952:.
1940::
1917:.
1903::
1876:.
1864::
1841:.
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1795:.
1771::
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1732::
1709:.
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1559::
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1370::
1344:.
1332::
1293:.
1281::
1255:.
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1201:.
1179::
1152:.
1130::
1100:.
1076::
1033:/
960:S
956:R
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840:R
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726:/
724:R
720:Z
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712:Z
708:Z
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688:Z
684:Z
680:Z
676:Z
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664:Z
660:Z
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510:H
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58:R
54:S
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