1.0 2011-09-21 01:50:16 UTC 2017-04-03 04:56:44 UTC FDB029112 11-Hydroxyeicosatetraenoate glyceryl ester 11(R)-HETE is produced from arachidonic acid by both COX-1 and COX-2 (cyclooxygenases). Using a model of intestinal epithelial cells that express the COX-2 permanently, 11(R)-HETE is produced upon stimulation. However, 11(R)-HETE is not detected in intact cells. Endothelial cells release several factors which influence vascular tone, leukocyte function and platelet aggregation; 11(R)-HETE is one of these factors. (PMID: 15964853, 8555273) [HMDB] (11S)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl-2-glyceryl ester (5Z,8Z,12E,14Z)-11S-hydroxyeicosatetraenoyl-2-glyceryl ester 11-HETE-G 2-[(11S)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-glycerol C23H38O5 394.5448 394.271924326 1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate 1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate 73347-43-0 CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1 SSHLWLAPLZCWOT-XYOZOUKRSA-N belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail. Endocannabinoids Organic compounds Lipids and lipid-like molecules Endocannabinoids Aliphatic acyclic compounds 2-monoacylglycerols Carbonyl compounds Carboxylic acid esters Fatty acid esters Fatty alcohols Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Other hydroxyeicosapolyenoic acids Primary alcohols Secondary alcohols 2-acyl-sn-glycerol 2-arachidonoylglycerol-skeleton Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Eicosanoid Fatty acid ester Fatty acyl Fatty alcohol Glycerolipid Hydrocarbon derivative Hydroxyeicosapolyenoic acid Monoacylglycerol Monocarboxylic acid or derivatives Monoradylglycerol Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Secondary alcohol Solid logp 4.62 ALOGPS logs -4.60 ALOGPS solubility 9.94e-03 g/l ALOGPS logp 4.18 ChemAxon pka_strongest_acidic 14.28 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate ChemAxon average_mass 394.5448 ChemAxon mono_mass 394.271924326 ChemAxon smiles CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO ChemAxon formula C23H38O5 ChemAxon inchi InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1 ChemAxon inchikey SSHLWLAPLZCWOT-XYOZOUKRSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 118.49 ChemAxon polarizability 45.89 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 39945 Specdb::CMs 132576 Specdb::CMs 140310 Specdb::MsMs 661465 Specdb::MsMs 661466 Specdb::MsMs 661467 Specdb::MsMs 2562531 Specdb::MsMs 2562532 Specdb::MsMs 2562533 Specdb::MsMs 2822471 Specdb::MsMs 2822472 Specdb::MsMs 2822473 Specdb::MsMs 2860111 Specdb::MsMs 2860112 Specdb::MsMs 2860113 Specdb::MsMs 3091843 Specdb::MsMs 3091844 Specdb::MsMs 3091845 HMDB12530 #<Reference:0x000055ce3322f5e0> #<Reference:0x000055ce3322f428>