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Record Information
Version3.6
Creation Date2006-08-14 00:02:12 UTC
Update Date2013-02-09 00:13:17 UTC
HMDB IDHMDB04673
Secondary Accession Numbers
  • HMDB03978
Metabolite Identification
Common Name11,12-Epoxyeicosatrienoic acid
Description11,12-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 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 , 11413051 , 10519554 ).
Structure
Thumb
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 FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Traditional Name(5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
CAS Registry Number81276-02-0
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 KeyDXOYQVHGIODESM-ATELOPIESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHepoxilins
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Epoxy Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
Direct ParentHepoxilins
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000327ALOGPS
logP6.25ALOGPS
logP5.65ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.36 m3·mol-1ChemAxon
Polarizability38.52 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Epidermis
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023399
KNApSAcK IDNot Available
Chemspider ID4510033
KEGG Compound IDC14770
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04673
Metagene LinkHMDB04673
METLIN ID7069
PubChem Compound5353269
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  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
  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
  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
  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
  34. Campbell WB: New role for epoxyeicosatrienoic acids as anti-inflammatory mediators. Trends Pharmacol Sci. 2000 Apr;21(4):125-7. Pubmed: 10740283
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  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
  49. Quilley J, McGiff JC: Is EDHF an epoxyeicosatrienoic acid? Trends Pharmacol Sci. 2000 Apr;21(4):121-4. Pubmed: 10740282
  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
  51. Kotlikoff MI: EDHF redux: EETs, TRPV4, and Ca2+ sparks. Circ Res. 2005 Dec 9;97(12):1209-10. Pubmed: 16339490
  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
  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
  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
  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
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Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular weight:
56687.095
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP4B1
Uniprot ID:
P13584
Molecular weight:
58990.64
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Molecular weight:
59085.45
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
General function:
Involved in monooxygenase activity
Specific function:
Has a potential importance for extrahepatic xenobiotic metabolism.
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Molecular weight:
55816.205
General function:
Involved in monooxygenase activity
Specific function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular weight:
57610.165
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2A7
Uniprot ID:
P20853
Molecular weight:
56424.735
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:
EPHX2
Uniprot ID:
P34913
Molecular weight:
62615.22
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP1A1
Uniprot ID:
A0N0X8
Molecular weight:
58164.8
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0
Molecular weight:
55729.9