1.0 2011-09-21 00:32:21 UTC 2015-07-21 06:57:47 UTC FDB023608 15(S)-Hydroxyeicosatrienoic acid 15(S)-hydroxyeicosatrienoic acid (15S-HETrE) is the in vivo metabolite of gamma-linolenic acid, a polyunsaturated fatty acid that have been reported to modulate arachidonic acid (AA) metabolism and tumorigenesis. 15S-HETrE suppress cyclooxygenase-2 (COX-2) over expression and/or Prostaglandin E2 (PGE2) biosynthesis (PMID 15197770), and inhibits [(3)H]thymidine uptake in parallel with the upregulation of peroxisome proliferator-activated receptor-gamma expression (a growth modulating nuclear receptor, PPARgamma). (PMID 12445673) [HMDB] 15-HETrE 15-hydroxy-(8Z,11Z,13E)-eicosatrienoate 15-hydroxy-(8Z,11Z,13E)-eicosatrienoic acid 15-hydroxy-cis,cis,trans-8,11,13-eicosatrienoate 15-hydroxy-cis,cis,trans-8,11,13-eicosatrienoic acid 15-hydroxyeicosatrienoate 15-hydroxyeicosatrienoic acid 15(S)-hydroxyeicosatrienoate 15(S)-hydroxyeicosatrienoic acid 15S-HETrE 15S-hydroxy-8Z,11Z,13E-eicosatrienoate 15S-hydroxy-8Z,11Z,13E-eicosatrienoic acid C20H34O3 322.4822 322.250794954 (15S)-15-hydroxyicosa-8,11,13-trienoic acid (15S)-15-hydroxyicosa-8,11,13-trienoic acid 13-16-1 [H][C@](O)(CCCCC)C=CC=CCC=CCCCCCCC(O)=O InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1 IUKXMNDGTWTNTP-IBGZPJMESA-N belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. Hydroxyeicosatrienoic acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Eicosanoids Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Unsaturated fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Hydroxy fatty acid Hydroxyeicosatrienoic acid Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Solid logp 6.20 ALOGPS logs -5.55 ALOGPS solubility 9.02e-04 g/l ALOGPS logp 5.72 ChemAxon pka_strongest_acidic 4.89 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (15S)-15-hydroxyicosa-8,11,13-trienoic acid ChemAxon average_mass 322.4822 ChemAxon mono_mass 322.250794954 ChemAxon smiles [H][C@](O)(CCCCC)C=CC=CCC=CCCCCCCC(O)=O ChemAxon formula C20H34O3 ChemAxon inchi InChI=1S/C20H34O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,9,11,14,17,19,21H,2-3,6-8,10,12-13,15-16,18H2,1H3,(H,22,23)/t19-/m0/s1 ChemAxon inchikey IUKXMNDGTWTNTP-IBGZPJMESA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 100.35 ChemAxon polarizability 40.98 ChemAxon rotatable_bond_count 15 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB05045 #<Reference:0x000055ce30761390> #<Reference:0x000055ce307611d8> 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