1.0 2011-09-21 00:29:21 UTC 2020-04-21 18:03:41 UTC FDB023399 11,12-Epoxyeicosatrienoic acid 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, 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 acid 10-(3-(2-octenyl)oxiranyl)-5,8-Decadienoate 10-(3-(2-octenyl)oxiranyl)-5,8-Decadienoic acid 11,12-EET 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoate 11,12-Epoxy-(5Z,8Z,14Z)-eicosatrienoic acid 11,12-epoxy-5,8,14-eicosatrienoate 11,12-epoxy-5,8,14-eicosatrienoic acid 11,12-Epoxyeicosatrienoate 11,12-Epoxyeicosatrienoic acid 11,12-Oxido-5,8,14-eicosatrienoate 11,12-Oxido-5,8,14-eicosatrienoic acid C20H32O3 320.4663 320.23514489 (5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid 11,12-epoxyeicosatrienoic acid 81276-02-0 CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=O 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+ 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. Hepoxilins Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Epoxides Epoxy fatty acids Hydrocarbon derivatives Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Unsaturated fatty acids Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dialkyl ether Epoxy fatty acid Ether Fatty acid Hepoxilin Heterocyclic fatty acid Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Unsaturated fatty acid Solid logp 6.25 ALOGPS logs -5.99 ALOGPS solubility 3.27e-04 g/l ALOGPS logp 5.65 ChemAxon pka_strongest_acidic 4.82 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (5E,8E)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles CCCCC\C=C\CC1OC1C\C=C\C\C=C\CCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi 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+ ChemAxon inchikey DXOYQVHGIODESM-ATELOPIESA-N ChemAxon polar_surface_area 49.83 ChemAxon refractivity 98.36 ChemAxon polarizability 38.52 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Arachidonic Acid Metabolism SMP00075 map00590 Specdb::CMs 15723 Specdb::CMs 38784 Specdb::MsMs 300853 Specdb::MsMs 300854 Specdb::MsMs 300855 Specdb::MsMs 343225 Specdb::MsMs 343226 Specdb::MsMs 343227 HMDB04673 #<Reference:0x000055ce31c6fa70> #<Reference:0x000055ce31c6f890> #<Reference:0x000055ce31c6f6b0> #<Reference:0x000055ce31c6f4f8> #<Reference:0x000055ce31c6f2c8> #<Reference:0x000055ce31c6f0e8> 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#<Reference:0x000055ce31c6b038> #<Reference:0x000055ce31c6ae80> #<Reference:0x000055ce31c6acc8> #<Reference:0x000055ce31c6aac0> #<Reference:0x000055ce31c6a908> #<Reference:0x000055ce31c6a750> #<Reference:0x000055ce31c6a520> #<Reference:0x000055ce31c6a340> #<Reference:0x000055ce31c6a138> #<Reference:0x000055ce31c69f08> #<Reference:0x000055ce31c69c88> #<Reference:0x000055ce31c699e0> #<Reference:0x000055ce31c697d8> #<Reference:0x000055ce31c69620> #<Reference:0x000055ce31c69440> #<Reference:0x000055ce31c69260> #<Reference:0x000055ce31c690a8> #<Reference:0x000055ce31c68ef0> #<Reference:0x000055ce31c68d38> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Cytochrome P450 2D6 Q6NWU0 CYP2D6 Cytochrome P450, family 1, subfamily A, polypeptide 1 A0N0X8 CYP1A1