Human Metabolome Database Version 3.5

Showing metabocard for 11,12-Epoxyeicosatrienoic acid (HMDB04673)

Record Information
Version 3.5
Creation Date 2006-08-13 18:02:12 -0600
Update Date 2013-02-08 17:13:17 -0700
HMDB ID HMDB04673
Secondary Accession Numbers
  • HMDB03978
Metabolite Identification
Common Name 11,12-Epoxyeicosatrienoic acid
Description 11,12-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid (EET). Induction of CYP2C8 in native coronary artery endothelial cells by beta-naphthoflavone enhances the formation of 11,12-epoxyeicosatrienoic acid, as well as endothelium-derived hyperpolarizing factor-mediated hyperpolarization and relaxation. Transfection of coronary arteries with CYP2C8 antisense oligonucleotides resulted in decreased levels of CYP2C and attenuated the endothelium-derived hyperpolarizing factor-mediated vascular responses. Thus, a CYP-epoxygenase product is an essential component of the endothelium-derived hyperpolarizing factor-mediated relaxation in the porcine coronary artery, and CYP2C8 fulfills the criteria for the coronary endothelium-derived hyperpolarization factor synthase. The role of EETs in regulation of the cerebral circulation has become more important, since it was realized that EETs are produced in another specialized cell type of the brain, the astrocytes. It has become evident that EETs released from astrocytes may mediate cerebral functional hyperemia. Molecular and pharmacological evidence hve shown that neurotransmitter release and spillover onto astrocytes can generate EETs. Since these EETs may reach the vasculature via astrocyte foot-processes, they have the same potential as their endothelial counterparts to hyperpolarize and dilate cerebral vessels. P450 enzymes contain heme in their catalytic domain and nitric oxide (NO) appears to bind to these heme moieties and block formation of P450 products, including EETs. Thus, there appears to be crosstalk between P450 enzymes and NO/NO synthase. The role of fatty acid metabolites and cerebral blood flow becomes even more complex in light of data demonstrating that cyclooxygenase products can act as substrates for P450 enzymes. (PMID: 17494091 Link_out, 17468203 Link_out, 17434916 Link_out, 17406062 Link_out, 17361113 Link_out, 15581597 Link_out, 11413051 Link_out, 10519554 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoate
  2. (5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoic acid
  3. (5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoate
  4. (5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoic acid
  5. 10-(3-(2-Octenyl)oxiranyl)-5,8-Decadienoate
  6. 10-(3-(2-Octenyl)oxiranyl)-5,8-Decadienoic acid
  7. 11,12-EET
  8. 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoate
  9. 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid
  10. 11,12-Epoxy-5,8,14-eicosatrienoate
  11. 11,12-Epoxy-5,8,14-eicosatrienoic acid
  12. 11,12-Epoxyeicosatrienoate
  13. 11,12-Epoxyeicosatrienoic acid
  14. 11,12-Oxido-5,8,14-eicosatrienoate
  15. 11,12-Oxido-5,8,14-eicosatrienoic acid
Chemical Formula C20H32O3
Average Molecular Weight 320.4663
Monoisotopic Molecular Weight 320.23514489
IUPAC Name (5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Traditional IUPAC Name (5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
CAS Registry Number 81276-02-0
SMILES CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=O
InChI Identifier InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6+,12-9+,13-10+
InChI Key DXOYQVHGIODESM-ATELOPIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hepoxilins
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Epoxy Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
Direct Parent Hepoxilins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.270E-04 g/L ALOGPS
LogP 6.25 ALOGPS
LogP 5.65 ChemAxon
LogS -5.99 ALOGPS
pKa (strongest acidic) 4.82 ChemAxon
pKa (strongest basic) -4.2 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 49.83 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 98.36 ChemAxon
Polarizability 38.52 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Epidermis
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 map00590 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023399
KNApSAcK ID Not Available
Chemspider ID 4510033 Link_out
KEGG Compound ID C14770 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04673 Link_out
Metagene Link HMDB04673 Link_out
METLIN ID 7069 Link_out
PubChem Compound 5353269 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Fang X, Kaduce TL, VanRollins M, Weintraub NL, Spector AA: Conversion of epoxyeicosatrienoic acids (EETs) to chain-shortened epoxy fatty acids by human skin fibroblasts. J Lipid Res. 2000 Jan;41(1):66-74. Pubmed: 10627503 Link_out
  2. Sacerdoti D, Gatta A, McGiff JC: Role of cytochrome P450-dependent arachidonic acid metabolites in liver physiology and pathophysiology. Prostaglandins Other Lipid Mediat. 2003 Oct;72(1-2):51-71. Pubmed: 14626496 Link_out
  3. Archer SL, Gragasin FS, Wu X, Wang S, McMurtry S, Kim DH, Platonov M, Koshal A, Hashimoto K, Campbell WB, Falck JR, Michelakis ED: Endothelium-derived hyperpolarizing factor in human internal mammary artery is 11,12-epoxyeicosatrienoic acid and causes relaxation by activating smooth muscle BK(Ca) channels. Circulation. 2003 Feb 11;107(5):769-76. Pubmed: 12578883 Link_out
  4. Potente M, Michaelis UR, Fisslthaler B, Busse R, Fleming I: Cytochrome P450 2C9-induced endothelial cell proliferation involves induction of mitogen-activated protein (MAP) kinase phosphatase-1, inhibition of the c-Jun N-terminal kinase, and up-regulation of cyclin D1. J Biol Chem. 2002 May 3;277(18):15671-6. Epub 2002 Feb 26. Pubmed: 11867622 Link_out
  5. Lundblad MS, Stark K, Eliasson E, Oliw E, Rane A: Biosynthesis of epoxyeicosatrienoic acids varies between polymorphic CYP2C enzymes. Biochem Biophys Res Commun. 2005 Feb 25;327(4):1052-7. Pubmed: 15652503 Link_out
  6. Node K, Huo Y, Ruan X, Yang B, Spiecker M, Ley K, Zeldin DC, Liao JK: Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science. 1999 Aug 20;285(5431):1276-9. Pubmed: 10455056 Link_out
  7. Luo G, Zeldin DC, Blaisdell JA, Hodgson E, Goldstein JA: Cloning and expression of murine CYP2Cs and their ability to metabolize arachidonic acid. Arch Biochem Biophys. 1998 Sep 1;357(1):45-57. Pubmed: 9721182 Link_out
  8. Schafer W, Werner K, Schweer H, Schneider J, Zahradnik HP: Formation of cytochrome P450 metabolites of arachidonic acid by human placenta. Adv Exp Med Biol. 1997;433:411-3. Pubmed: 9561183 Link_out
  9. VanRollins M, Kaduce TL, Knapp HR, Spector AA: 14,15-Epoxyeicosatrienoic acid metabolism in endothelial cells. J Lipid Res. 1993 Nov;34(11):1931-42. Pubmed: 8263417 Link_out
  10. Thum T, Borlak J: Mechanistic role of cytochrome P450 monooxygenases in oxidized low-density lipoprotein-induced vascular injury: therapy through LOX-1 receptor antagonism? Circ Res. 2004 Jan 9;94(1):e1-13. Epub 2003 Dec 4. Pubmed: 14656932 Link_out
  11. Potente M, Fisslthaler B, Busse R, Fleming I: 11,12-Epoxyeicosatrienoic acid-induced inhibition of FOXO factors promotes endothelial proliferation by down-regulating p27Kip1. J Biol Chem. 2003 Aug 8;278(32):29619-25. Epub 2003 May 28. Pubmed: 12773534 Link_out
  12. Fisslthaler B, Popp R, Michaelis UR, Kiss L, Fleming I, Busse R: Cyclic stretch enhances the expression and activity of coronary endothelium-derived hyperpolarizing factor synthase. Hypertension. 2001 Dec 1;38(6):1427-32. Pubmed: 11751730 Link_out
  13. Fukao M, Mason HS, Kenyon JL, Horowitz B, Keef KD: Regulation of BK(Ca) channels expressed in human embryonic kidney 293 cells by epoxyeicosatrienoic acid. Mol Pharmacol. 2001 Jan;59(1):16-23. Pubmed: 11125019 Link_out
  14. Daikh BE, Lasker JM, Raucy JL, Koop DR: Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. J Pharmacol Exp Ther. 1994 Dec;271(3):1427-33. Pubmed: 7996455 Link_out
  15. Pritchard KA Jr, Wong PY, Stemerman MB: Atherogenic concentrations of low-density lipoprotein enhance endothelial cell generation of epoxyeicosatrienoic acid products. Am J Pathol. 1990 Jun;136(6):1383-91. Pubmed: 2356865 Link_out
  16. Sun J, Sui X, Bradbury JA, Zeldin DC, Conte MS, Liao JK: Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids. Circ Res. 2002 May 17;90(9):1020-7. Pubmed: 12016269 Link_out
  17. Zeldin DC, Foley J, Ma J, Boyle JE, Pascual JM, Moomaw CR, Tomer KB, Steenbergen C, Wu S: CYP2J subfamily P450s in the lung: expression, localization, and potential functional significance. Mol Pharmacol. 1996 Nov;50(5):1111-7. Pubmed: 8913342 Link_out
  18. Rifkind AB, Lee C, Chang TK, Waxman DJ: Arachidonic acid metabolism by human cytochrome P450s 2C8, 2C9, 2E1, and 1A2: regioselective oxygenation and evidence for a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes. Arch Biochem Biophys. 1995 Jul 10;320(2):380-9. Pubmed: 7625847 Link_out
  19. Spiecker M, Liao JK: Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids. Arch Biochem Biophys. 2005 Jan 15;433(2):413-20. Pubmed: 15581597 Link_out
  20. Fleming I, Michaelis UR, Bredenkotter D, Fisslthaler B, Dehghani F, Brandes RP, Busse R: Endothelium-derived hyperpolarizing factor synthase (Cytochrome P450 2C9) is a functionally significant source of reactive oxygen species in coronary arteries. Circ Res. 2001 Jan 19;88(1):44-51. Pubmed: 11139472 Link_out
  21. Popp R, Brandes RP, Ott G, Busse R, Fleming I: Dynamic modulation of interendothelial gap junctional communication by 11,12-epoxyeicosatrienoic acid. Circ Res. 2002 Apr 19;90(7):800-6. Pubmed: 11964373 Link_out
  22. Revtyak GE, Hughes MJ, Johnson AR, Campbell WB: Histamine stimulation of prostaglandin and HETE synthesis in human endothelial cells. Am J Physiol. 1988 Aug;255(2 Pt 1):C214-25. Pubmed: 3407766 Link_out
  23. Fitzpatrick FA, Ennis MD, Baze ME, Wynalda MA, McGee JE, Liggett WF: Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. Influence of stereochemistry. J Biol Chem. 1986 Nov 15;261(32):15334-8. Pubmed: 3095326 Link_out
  24. Anton R, Abian J, Vila L: Characterization of arachidonic acid metabolites through the 12-lipoxygenase pathway in human epidermis by high-performance liquid chromatography and gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 1995;Spec No:S169-82. Pubmed: 8829479 Link_out
  25. Arima S, Endo Y, Yaoita H, Omata K, Ogawa S, Tsunoda K, Abe M, Takeuchi K, Abe K, Ito S: Possible role of P-450 metabolite of arachidonic acid in vasodilator mechanism of angiotensin II type 2 receptor in the isolated microperfused rabbit afferent arteriole. J Clin Invest. 1997 Dec 1;100(11):2816-23. Pubmed: 9389747 Link_out
  26. Fisslthaler B, Popp R, Kiss L, Potente M, Harder DR, Fleming I, Busse R: Cytochrome P450 2C is an EDHF synthase in coronary arteries. Nature. 1999 Sep 30;401(6752):493-7. Pubmed: 10519554 Link_out
  27. Zhu Y, Schieber EB, McGiff JC, Balazy M: Identification of arachidonate P-450 metabolites in human platelet phospholipids. Hypertension. 1995 Apr;25(4 Pt 2):854-9. Pubmed: 7721444 Link_out
  28. McGee J, Fitzpatrick F: Enzymatic hydration of leukotriene A4. Purification and characterization of a novel epoxide hydrolase from human erythrocytes. J Biol Chem. 1985 Oct 15;260(23):12832-7. Pubmed: 2995393 Link_out
  29. Catella F, Lawson JA, Fitzgerald DJ, FitzGerald GA: Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proc Natl Acad Sci U S A. 1990 Aug;87(15):5893-7. Pubmed: 2198572 Link_out
  30. Catella F, Lawson J, Braden G, Fitzgerald DJ, Shipp E, FitzGerald GA: Biosynthesis of P450 products of arachidonic acid in humans: increased formation in cardiovascular disease. Adv Prostaglandin Thromboxane Leukot Res. 1991;21A:193-6. Pubmed: 1705382 Link_out
  31. Michaelis UR, Falck JR, Schmidt R, Busse R, Fleming I: Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells. Arterioscler Thromb Vasc Biol. 2005 Feb;25(2):321-6. Epub 2004 Nov 29. Pubmed: 15569819 Link_out
  32. Lu T, Hong MP, Lee HC: Molecular determinants of cardiac K(ATP) channel activation by epoxyeicosatrienoic acids. J Biol Chem. 2005 May 13;280(19):19097-104. Epub 2005 Mar 10. Pubmed: 15760904 Link_out
  33. Larsen BT, Miura H, Hatoum OA, Campbell WB, Hammock BD, Zeldin DC, Falck JR, Gutterman DD: Epoxyeicosatrienoic and dihydroxyeicosatrienoic acids dilate human coronary arterioles via BK(Ca) channels: implications for soluble epoxide hydrolase inhibition. Am J Physiol Heart Circ Physiol. 2006 Feb;290(2):H491-9. Epub 2005 Oct 28. Pubmed: 16258029 Link_out
  34. Campbell WB: New role for epoxyeicosatrienoic acids as anti-inflammatory mediators. Trends Pharmacol Sci. 2000 Apr;21(4):125-7. Pubmed: 10740283 Link_out
  35. Wu S, Chen W, Murphy E, Gabel S, Tomer KB, Foley J, Steenbergen C, Falck JR, Moomaw CR, Zeldin DC: Molecular cloning, expression, and functional significance of a cytochrome P450 highly expressed in rat heart myocytes. J Biol Chem. 1997 May 9;272(19):12551-9. Pubmed: 9139707 Link_out
  36. Muller DN, Theuer J, Shagdarsuren E, Kaergel E, Honeck H, Park JK, Markovic M, Barbosa-Sicard E, Dechend R, Wellner M, Kirsch T, Fiebeler A, Rothe M, Haller H, Luft FC, Schunck WH: A peroxisome proliferator-activated receptor-alpha activator induces renal CYP2C23 activity and protects from angiotensin II-induced renal injury. Am J Pathol. 2004 Feb;164(2):521-32. Pubmed: 14742258 Link_out
  37. Karara A, Dishman E, Jacobson H, Falck JR, Capdevila JH: Arachidonic acid epoxygenase. Stereochemical analysis of the endogenous epoxyeicosatrienoic acids of human kidney cortex. FEBS Lett. 1990 Jul 30;268(1):227-30. Pubmed: 2384159 Link_out
  38. Medhora M, Narayanan J, Harder D: Dual regulation of the cerebral microvasculature by epoxyeicosatrienoic acids. Trends Cardiovasc Med. 2001 Jan;11(1):38-42. Pubmed: 11413051 Link_out
  39. Dray F, Vulliez-Le Normand B, Deroussent A, Briquet I, Gabellec MM, Nakamura S, Wahl LM, Gouyette A, Salahuddin ZS: Active metabolism of arachidonic acid by Kaposi sarcoma cells cultured from lung biopsies (KS-3); identification by HPLC and MS/MS of the predominant metabolite secreted as the 11,12-epoxy-eicosatrienoic acid. Biochim Biophys Acta. 1992 Oct 13;1180(1):83-90. Pubmed: 1390946 Link_out
  40. Michaelis UR, Fisslthaler B, Medhora M, Harder D, Fleming I, Busse R: Cytochrome P450 2C9-derived epoxyeicosatrienoic acids induce angiogenesis via cross-talk with the epidermal growth factor receptor (EGFR). FASEB J. 2003 Apr;17(6):770-2. Epub 2003 Feb 5. Pubmed: 12586744 Link_out
  41. Jacobs ER, Zeldin DC: The lung HETEs (and EETs) up. Am J Physiol Heart Circ Physiol. 2001 Jan;280(1):H1-H10. Pubmed: 11123211 Link_out
  42. Kiss L, Schutte H, Mayer K, Grimm H, Padberg W, Seeger W, Grimminger F: Synthesis of arachidonic acid-derived lipoxygenase and cytochrome P450 products in the intact human lung vasculature. Am J Respir Crit Care Med. 2000 Jun;161(6):1917-23. Pubmed: 10852767 Link_out
  43. Honda HM, Leitinger N, Frankel M, Goldhaber JI, Natarajan R, Nadler JL, Weiss JN, Berliner JA: Induction of monocyte binding to endothelial cells by MM-LDL: role of lipoxygenase metabolites. Arterioscler Thromb Vasc Biol. 1999 Mar;19(3):680-6. Pubmed: 10073973 Link_out
  44. Xiao YF, Ke Q, Seubert JM, Bradbury JA, Graves J, Degraff LM, Falck JR, Krausz K, Gelboin HV, Morgan JP, Zeldin DC: Enhancement of cardiac L-type Ca2+ currents in transgenic mice with cardiac-specific overexpression of CYP2J2. Mol Pharmacol. 2004 Dec;66(6):1607-16. Epub 2004 Sep 10. Pubmed: 15361551 Link_out
  45. Node K, Ruan XL, Dai J, Yang SX, Graham L, Zeldin DC, Liao JK: Activation of Galpha s mediates induction of tissue-type plasminogen activator gene transcription by epoxyeicosatrienoic acids. J Biol Chem. 2001 May 11;276(19):15983-9. Epub 2001 Feb 22. Pubmed: 11279071 Link_out
  46. Fleming I, Fisslthaler B, Michaelis UR, Kiss L, Popp R, Busse R: The coronary endothelium-derived hyperpolarizing factor (EDHF) stimulates multiple signalling pathways and proliferation in vascular cells. Pflugers Arch. 2001 Jul;442(4):511-8. Pubmed: 11510882 Link_out
  47. Falck JR, Reddy LM, Reddy YK, Bondlela M, Krishna UM, Ji Y, Sun J, Liao JK: 11,12-epoxyeicosatrienoic acid (11,12-EET): structural determinants for inhibition of TNF-alpha-induced VCAM-1 expression. Bioorg Med Chem Lett. 2003 Nov 17;13(22):4011-4. Pubmed: 14592496 Link_out
  48. Krotz F, Riexinger T, Buerkle MA, Nithipatikom K, Gloe T, Sohn HY, Campbell WB, Pohl U: Membrane-potential-dependent inhibition of platelet adhesion to endothelial cells by epoxyeicosatrienoic acids. Arterioscler Thromb Vasc Biol. 2004 Mar;24(3):595-600. Epub 2004 Jan 8. Pubmed: 14715644 Link_out
  49. Quilley J, McGiff JC: Is EDHF an epoxyeicosatrienoic acid? Trends Pharmacol Sci. 2000 Apr;21(4):121-4. Pubmed: 10740282 Link_out
  50. Treluyer JM, Benech H, Colin I, Pruvost A, Cheron G, Cresteil T: Ontogenesis of CYP2C-dependent arachidonic acid metabolism in the human liver: relationship with sudden infant death syndrome. Pediatr Res. 2000 May;47(5):677-83. Pubmed: 10813596 Link_out
  51. Kotlikoff MI: EDHF redux: EETs, TRPV4, and Ca2+ sparks. Circ Res. 2005 Dec 9;97(12):1209-10. Pubmed: 16339490 Link_out
  52. Mombouli JV, Holzmann S, Kostner GM, Graier WF: Potentiation of Ca2+ signaling in endothelial cells by 11,12-epoxyeicosatrienoic acid. J Cardiovasc Pharmacol. 1999 May;33(5):779-84. Pubmed: 10226866 Link_out
  53. Ulsaker GA, Teien G: Gas chromatographic-mass spectrometric identification of four triene monoepoxides of arachidonic acid in human plasma. Analyst. 1990 Mar;115(3):259-62. Pubmed: 2327589 Link_out
  54. Michaelis UR, Fisslthaler B, Barbosa-Sicard E, Falck JR, Fleming I, Busse R: Cytochrome P450 epoxygenases 2C8 and 2C9 are implicated in hypoxia-induced endothelial cell migration and angiogenesis. J Cell Sci. 2005 Dec 1;118(Pt 23):5489-98. Epub 2005 Nov 15. Pubmed: 16291720 Link_out
  55. Balazy M, Schieber EB, McGiff JC: Identification of arachidonate epoxides in human platelets. Adv Prostaglandin Thromboxane Leukot Res. 1995;23:199-201. Pubmed: 7732834 Link_out
  56. VanRollins M: Epoxygenase metabolites of docosahexaenoic and eicosapentaenoic acids inhibit platelet aggregation at concentrations below those affecting thromboxane synthesis. J Pharmacol Exp Ther. 1995 Aug;274(2):798-804. Pubmed: 7636743 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A43
Reactions: Not Available
Gene Name: CYP3A43
Uniprot ID: Q9HB55 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1B1
Reactions: Not Available
Gene Name: CYP1B1
Uniprot ID: Q16678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C18
Reactions: Not Available
Gene Name: CYP2C18
Uniprot ID: P33260 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2F1
Reactions: Not Available
Gene Name: CYP2F1
Uniprot ID: P24903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4X1
Reactions: Not Available
Gene Name: CYP4X1
Uniprot ID: Q8N118 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2B6
Reactions: Not Available
Gene Name: CYP2B6
Uniprot ID: P20813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A13
Reactions: Not Available
Gene Name: CYP2A13
Uniprot ID: Q16696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4B1
Reactions: Not Available
Gene Name: CYP4B1
Uniprot ID: P13584 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4Z1
Reactions: Not Available
Gene Name: CYP4Z1
Uniprot ID: Q86W10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2S1
Reactions: Not Available
Gene Name: CYP2S1
Uniprot ID: Q96SQ9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2J2
Reactions: Not Available
Gene Name: CYP2J2
Uniprot ID: P51589 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A7
Reactions: Not Available
Gene Name: CYP2A7
Uniprot ID: P20853 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2A6
Reactions: Not Available
Gene Name: CYP2A6
Uniprot ID: P11509 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional epoxide hydrolase 2
Reactions: Not Available
Gene Name: EPHX2
Uniprot ID: P34913 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 1, subfamily A, polypeptide 1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: A0N0X8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: Q6NWU0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA