1.0 2011-09-21 01:58:13 UTC 2015-07-21 06:59:46 UTC FDB029598 16(17)-EpDPE 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. 16(17)-EpETE is the DHA homolog of 14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of docosahexaenoic acid (DHA). The EDHF activity of 16(17)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model [HMDB] 16(17)-EpDoPE C22H32O3 344.4877 344.23514489 (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid (4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12- BCTXZWCPBLWCRV-ZYADFMMDSA-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 Docosanoids EpDPE Solid logp 6.16 ALOGPS logs -6.10 ALOGPS solubility 2.74e-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)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid ChemAxon average_mass 344.4877 ChemAxon mono_mass 344.23514489 ChemAxon smiles CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O ChemAxon formula C22H32O3 ChemAxon inchi InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12- ChemAxon inchikey BCTXZWCPBLWCRV-ZYADFMMDSA-N ChemAxon polar_surface_area 49.83 ChemAxon refractivity 109.79 ChemAxon polarizability 40.41 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21940 Specdb::CMs 40132 Specdb::CMs 156194 Specdb::MsMs 314740 Specdb::MsMs 314741 Specdb::MsMs 314742 Specdb::MsMs 360547 Specdb::MsMs 360548 Specdb::MsMs 360549 Specdb::MsMs 3057134 Specdb::MsMs 3057135 Specdb::MsMs 3057136 Specdb::MsMs 3113198 Specdb::MsMs 3113199 Specdb::MsMs 3113200 HMDB13621 #<Reference:0x000055ce318e21f0> #<Reference:0x000055ce318e2038> #<Reference:0x000055ce318e1e80> #<Reference:0x000055ce318e1cc8>