1.0 2011-09-21 01:58:12 UTC 2017-04-03 05:02:20 UTC FDB029597 19(20)-EpDPE 19(20)-EpDPE is a DHA epoxygenase metabolite, derived via epoxidation of the w-3 double bond of DHA. The EDHF activity of 19(20)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model EDHF (endothelium-derived hyperpolarizing factor) is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators.1,2 Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator.3 However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites. 1 [HMDB] 19,20-EDP 19,20-Epoxydocosapentaenoate 19,20-Epoxydocosapentaenoic acid 19(20)-EpDoPE 19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoate 19(20)-Epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid Epox 22:6n3 C22H32O3 344.4877 344.23514489 (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid 24880-45-3 CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14- OSXOPUBJJDUAOJ-MBYQGORISA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic heteromonocyclic compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Epoxides Epoxy fatty acids Hydrocarbon derivatives Long-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 Heterocyclic fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Unsaturated fatty acid Docosanoids EpDPE Solid logp 6.17 ALOGPS logs -6.15 ALOGPS solubility 2.44e-04 g/l ALOGPS logp 5.81 ChemAxon pka_strongest_acidic 4.89 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac (4Z,7Z,10Z,13Z,16Z)-18-(3-ethyloxiran-2-yl)octadeca-4,7,10,13,16-pentaenoic acid ChemAxon average_mass 344.4877 ChemAxon mono_mass 344.23514489 ChemAxon smiles CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O ChemAxon formula C22H32O3 ChemAxon inchi InChI=1S/C22H32O3/c1-2-20-21(25-20)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-22(23)24/h3-4,7-10,13-16,20-21H,2,5-6,11-12,17-19H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,15-13-,16-14- ChemAxon inchikey OSXOPUBJJDUAOJ-MBYQGORISA-N ChemAxon polar_surface_area 49.83 ChemAxon refractivity 109.79 ChemAxon polarizability 40.02 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17547 Specdb::CMs 40131 Specdb::CMs 160344 Specdb::MsMs 304837 Specdb::MsMs 304838 Specdb::MsMs 304839 Specdb::MsMs 348133 Specdb::MsMs 348134 Specdb::MsMs 348135 Specdb::MsMs 2373219 Specdb::MsMs 2373220 Specdb::MsMs 2373221 Specdb::MsMs 2565935 Specdb::MsMs 2565936 Specdb::MsMs 2565937 HMDB13620 #<Reference:0x000055ce334f5810> #<Reference:0x000055ce334f5658> #<Reference:0x000055ce334f54a0> #<Reference:0x000055ce334f52e8>