1.0 2011-09-21 00:21:44 UTC 2015-07-21 06:57:25 UTC FDB022920 8,9-Epoxyeicosatrienoic acid 8,9-Epoxyeicosatrienoic acid is an epoxyeicosatrienoic acid eicosanoid, a metabolite of arachidonic acid. The P450 epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091, 17468203, 17434916, 17406062, 17361113, 15581597) [HMDB] (+/-)8,9-EpETrE (5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoate (5Z,11Z,14Z)-8,9-Epoxyeicosa-5,11,14-trienoic acid (5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoate (5Z,11Z,14Z)-8,9-Epoxyicosa-5,11,14-trienoic acid 8,9-Eet 8,9-epoxy-5Z,11Z,14Z-eicosatrienoate 8,9-epoxy-5Z,11Z,14Z-eicosatrienoic acid 8,9-Epoxy-5Z,11Z,14Z-icosatrienoate 8,9-Epoxy-5Z,11Z,14Z-icosatrienoic acid 8,9-Epoxyeicosatrienoate 8,9-Epoxyeicosatrienoic acid 8,9-Epoxyicosatrienoate 8,9-Epoxyicosatrienoic acid C20H32O3 320.4663 320.23514489 7-[3-(undeca-2,5-dien-1-yl)oxiran-2-yl]hept-5-enoic acid 7-[3-(undeca-2,5-dien-1-yl)oxiran-2-yl]hept-5-enoic acid 81246-85-7 CCCCCC=CCC=CCC1OC1CC=CCCCC(O)=O InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22) DBWQSCSXHFNTMO-UHFFFAOYSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Epoxides Epoxy fatty acids Hydrocarbon derivatives 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 Heterocyclic fatty acid Hydrocarbon derivative Long-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 -6.00 ALOGPS solubility 3.20e-04 g/l ALOGPS logp 5.65 ChemAxon pka_strongest_acidic 4.46 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac 7-[3-(undeca-2,5-dien-1-yl)oxiran-2-yl]hept-5-enoic acid ChemAxon average_mass 320.4663 ChemAxon mono_mass 320.23514489 ChemAxon smiles CCCCCC=CCC=CCC1OC1CC=CCCCC(O)=O ChemAxon formula C20H32O3 ChemAxon inchi InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22) ChemAxon inchikey DBWQSCSXHFNTMO-UHFFFAOYSA-N ChemAxon polar_surface_area 49.83 ChemAxon refractivity 98.36 ChemAxon polarizability 38.55 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::MsMs 3411050 Specdb::MsMs 3411051 Specdb::MsMs 3411052 Specdb::MsMs 3411053 Specdb::MsMs 3411054 Specdb::MsMs 3411055 Specdb::CMs 111647 Specdb::CMs 124931 Specdb::CMs 126937 HMDB02232 #<Reference:0x000055ce31e0d148> 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