1.0 2011-09-21 01:26:32 UTC 2025-11-19 02:53:17 UTC FDB027560 11,12-EpETrE 11,12-EpETrE or 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid is an epoxyeicosatrienoic acid or an EET derived from arachadonic acid. EETs function as autacrine and paracrine mediators. During inflammation, a large amount of arachidonic acid (AA) is released into the cellular milieu and cyclooxygenase enzymes convert this AA to prostaglandins that in turn sensitize pain pathways. However, AA is also converted to natural epoxyeicosatrienoic acids (EETs) by cytochrome P450 enzymes. Cytochrome P450 (CYP) epoxygenases convert arachidonic acid to four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels. In particular, 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid has been show to play a role in the recovery of depleted Ca2+ pools in cultured smooth muscle cells (PMID: 9368016). In addition, EETs have antiinflammatory effects on blood vessels and in the kidney, promote angiogenesis, and protect ischemic myocardium and brain. EET levels are typically regulated by soluble epoxide hydrolase (sEH), the major enzyme degrading EETs. Specifically, soluble epoxide hydrolase (sEH) converts EETs to dihydroxyeicosatrienoic acids. [HMDB] (+/-)11,12-EpETrE (+/-)11(12)-EET (+/-)11(12)-EpETrE 11,12-epoxy-5Z,8Z,14Z-eicosatrienoate 11,12-epoxy-5Z,8Z,14Z-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 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 Specdb::CMs 15723 Specdb::CMs 38784 Specdb::MsMs 300853 Specdb::MsMs 300854 Specdb::MsMs 300855 Specdb::MsMs 343225 Specdb::MsMs 343226 Specdb::MsMs 343227 HMDB10409 #<Reference:0x000055ce31cff760>