1.0 2011-09-21 00:29:41 UTC 2015-07-21 06:57:42 UTC FDB023418 9,12,13-TriHOME 9,12,13-TriHOME is a trihydroxyoctadecenoic acid metabolite of linoleic acid, one of the major fatty acids found in lipids. Vascular tissue converts various polyunsaturated fatty acids to monohydroxy and trihydroxy metabolites derived from hydroperoxides which may be involved in regulating prostaglandin synthesis. The absolute amounts of 9,12,13-TriHOME varies considerably from one species to another. There are several possible mechanisms for the formation of esterified oxygenated polyunsaturated fatty acids: oxygenated and then incorporated into lipids, not well incorporated into either vascular endothelial or smooth muscle cells, or could accumulated in lipids either due to autoxidation in vivo or to the action of an enzyme similar to Iipoxygenase. (PMID: 3997883, 6414520) [HMDB] (10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoate (10E)-(9S,12S,13S)-9,12,13-Trihydroxyoctadec-10-enoic acid 9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoate 9(S),12(S),13(S)-Trihydroxy-10(E)-octadecenoic acid 9S,12S,13S-trihydroxy-10E-octadecenoate 9S,12S,13S-trihydroxy-10E-octadecenoic acid C18H34O5 330.4596 330.240624198 (9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid (9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid 97134-11-7 CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1 MDIUMSLCYIJBQC-MVFSOIOZSA-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 acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxy fatty acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Unsaturated fatty acid Other Octadecanoids Other Octadecanoids TriHOME Solid logp 3.77 ALOGPS logs -3.33 ALOGPS solubility 1.55e-01 g/l ALOGPS logp 3.25 ChemAxon pka_strongest_acidic 4.68 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (9S,10E,12S,13S)-9,12,13-trihydroxyoctadec-10-enoic acid ChemAxon average_mass 330.4596 ChemAxon mono_mass 330.240624198 ChemAxon smiles CCCCC[C@H](O)[C@@H](O)\C=C\[C@@H](O)CCCCCCCC(O)=O ChemAxon formula C18H34O5 ChemAxon inchi InChI=1S/C18H34O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h13-17,19-21H,2-12H2,1H3,(H,22,23)/b14-13+/t15-,16-,17-/m0/s1 ChemAxon inchikey MDIUMSLCYIJBQC-MVFSOIOZSA-N ChemAxon polar_surface_area 97.99 ChemAxon refractivity 91.79 ChemAxon polarizability 40.04 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18088 Specdb::CMs 38803 Specdb::CMs 169215 Specdb::MsMs 306100 Specdb::MsMs 306101 Specdb::MsMs 306102 Specdb::MsMs 349636 Specdb::MsMs 349637 Specdb::MsMs 349638 Specdb::MsMs 2711999 Specdb::MsMs 2712000 Specdb::MsMs 2712001 Specdb::MsMs 2996747 Specdb::MsMs 2996748 Specdb::MsMs 2996749 HMDB04708 #<Reference:0x000055ce2ca19de8> #<Reference:0x000055ce2ca19b68> 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