1.02011-09-21 00:29:21 UTC2020-04-21 18:03:41 UTCFDB02339911,12-Epoxyeicosatrienoic acid11,12-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) [HMDB](5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoate(5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoic acid(5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoate(5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoic acid10-(3-(2-octenyl)oxiranyl)-5,8-Decadienoate10-(3-(2-octenyl)oxiranyl)-5,8-Decadienoic acid11,12-EET11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoate11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid11,12-epoxy-5,8,14-eicosatrienoate11,12-epoxy-5,8,14-eicosatrienoic acid11,12-Epoxyeicosatrienoate11,12-Epoxyeicosatrienoic acid11,12-Oxido-5,8,14-eicosatrienoate11,12-Oxido-5,8,14-eicosatrienoic acidC20H32O3320.4663320.23514489(5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid11,12-epoxyeicosatrienoic acid81276-02-0CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=OInChI=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+DXOYQVHGIODESM-ATELOPIESA-N belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.HepoxilinsOrganic compoundsLipids and lipid-like moleculesFatty AcylsEicosanoidsAliphatic heteromonocyclic compoundsCarbonyl compoundsCarboxylic acidsDialkyl ethersEpoxidesEpoxy fatty acidsHydrocarbon derivativesMedium-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsUnsaturated fatty acidsAliphatic heteromonocyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeDialkyl etherEpoxy fatty acidEtherFatty acidHepoxilinHeterocyclic fatty acidHydrocarbon derivativeMedium-chain fatty acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxiraneUnsaturated fatty acidSolidlogp6.25logs-5.99solubility3.27e-04 g/llogp5.65pka_strongest_acidic4.82pka_strongest_basic-4.2iupac(5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acidaverage_mass320.4663mono_mass320.23514489smilesCCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=OformulaC20H32O3inchiInChI=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+inchikeyDXOYQVHGIODESM-ATELOPIESA-Npolar_surface_area49.83refractivity98.36polarizability38.52rotatable_bond_count14acceptor_count3donor_count1physiological_charge-1formal_charge0Arachidonic Acid MetabolismSMP00075map00590Specdb::CMs15723Specdb::CMs38784Specdb::MsMs300853Specdb::MsMs300854Specdb::MsMs300855Specdb::MsMs343225Specdb::MsMs343226Specdb::MsMs343227HMDB04673#<Reference:0x0000555675c43418>#<Reference:0x0000555675c43238>#<Reference:0x0000555675c43058>#<Reference:0x0000555675c42e78>#<Reference:0x0000555675c42c70>#<Reference:0x0000555675c42a40>#<Reference:0x0000555675c427c0>#<Reference:0x0000555675c42568>#<Reference:0x0000555675c42310>#<Reference:0x0000555675c42090>#<Reference:0x0000555675c41e88>#<Reference:0x0000555675c41cd0>#<Reference:0x0000555675c41b18>#<Reference:0x0000555675c41938>#<Reference:0x0000555675c41780>#<Reference:0x0000555675c415c8>#<Reference:0x0000555675c41410>#<Reference:0x0000555675c41258>#<Reference:0x0000555675c410a0>#<Reference:0x0000555675c40ee8>#<Reference:0x0000555675c40d30>#<Reference:0x0000555675c40b78>#<Reference:0x0000555675c409c0>#<Reference:0x0000555675c40808>#<Reference:0x0000555675c40650>#<Reference:0x0000555675c40498>#<Reference:0x0000555675c402e0>#<Reference:0x0000555675c40128>#<Reference:0x0000555675c3fed0>#<Reference:0x0000555675c3fc78>#<Reference:0x0000555675c3f9f8>#<Reference:0x0000555675c3f840>#<Reference:0x0000555675c3f688>#<Reference:0x0000555675c3f4a8>#<Reference:0x0000555675c3f2a0>#<Reference:0x0000555675c3f098>#<Reference:0x0000555675c3ee90>#<Reference:0x0000555675c3ec88>#<Reference:0x0000555675c3ea80>#<Reference:0x0000555675c3e8c8>#<Reference:0x0000555675c3e670>#<Reference:0x0000555675c3e440>#<Reference:0x0000555675c3e260>#<Reference:0x0000555675c3e030>#<Reference:0x0000555675c3de78>#<Reference:0x0000555675c3dc70>#<Reference:0x0000555675c3da90>#<Reference:0x0000555675c3d8d8>#<Reference:0x0000555675c3d720>#<Reference:0x0000555675c3d568>#<Reference:0x0000555675c3d3b0>#<Reference:0x0000555675c3d1a8>#<Reference:0x0000555675c3cfc8>#<Reference:0x0000555675c3ce10>#<Reference:0x0000555675c3cc30>#<Reference:0x0000555675c3ca28>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Cytochrome P450 2D6Q6NWU0CYP2D6Cytochrome P450, family 1, subfamily A, polypeptide 1A0N0X8CYP1A1