1.0 2016-09-30 23:10:04 UTC 2020-05-11 20:40:56 UTC BMDB0004667 BMDB04667 13S-hydroxyoctadecadienoic acid (13S)-Hydroxyoctadecadienoic acid (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid (13S)-Hydroxyoctadecadienoate (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate 13S-Hydroxyoctadecadienoate 13-Hydroxy-9,11-octadecadienoic acid 13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer 13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer 13-Hydroxyoctadecadienoic acid 13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer 13(S) HODE 13-Hydroxyoctadecadienoate (+)-Coriolic acid (13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid (9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid (9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid (9Z,11E,13S)-13-Hydroxyoctadecadienoic acid (S)-Coriolic acid (±)-coriolic acid 13-Hydroxy-9(Z),11(e)-octadecadienoic acid 13-Hydroxy-9,11-cis,trans-octadecadienoic acid 13-Hydroxy-9-cis-11-trans-octadecadienoic acid 13-Hydroxy-cis-9-trans-11-octadecadienoic acid 13-Hydroxylinoleic acid 13-Hydroxyoctadeca-9,11-dienoic acid 13S-HODE 13S-Hydroxy-9Z,11E-octadecadienoic acid L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid alpha-Artemisolic acid Α-artemisolic acid (9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate (9Z,11E)-13-HODE (9Z,11E)-13-Hydroxyoctadecadienoic acid FA(18:2(9Z,11E,13-OH)) FA(18:2(9Z,11E,13S-OH)) 13-HODE C18H32O3 296.4449 296.23514489 (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid 13-hydroxyoctadecadienoic acid 29623-28-7 CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1 HNICUWMFWZBIFP-IRQZEAMPSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Lineolic acids and derivatives 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 Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Unsaturated fatty acid Aliphatic acyclic compounds HODE Other Octadecanoids Other Octadecanoids Solid logp 5.88 ALOGPS logs -5.00 ALOGPS logp 5.19 ChemAxon pka_strongest_acidic 4.99 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid ChemAxon average_mass 296.4449 ChemAxon mono_mass 296.23514489 ChemAxon smiles CCCCC[C@H](O)\C=C\C=C/CCCCCCCC(O)=O ChemAxon formula C18H32O3 ChemAxon inchi InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1 ChemAxon inchikey HNICUWMFWZBIFP-IRQZEAMPSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 90.03 ChemAxon polarizability 37.26 ChemAxon rotatable_bond_count 14 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 26031 Specdb::CMs 38780 Specdb::CMs 153014 Specdb::MsMs 44925 Specdb::MsMs 44926 Specdb::MsMs 44927 Specdb::MsMs 159675 Specdb::MsMs 159676 Specdb::MsMs 159677 Specdb::MsMs 2769071 Specdb::MsMs 2769072 Specdb::MsMs 2769073 Specdb::MsMs 2912399 Specdb::MsMs 2912400 Specdb::MsMs 2912401 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 4947055 DB06926 FDB112215 6443013 C14762 34154 C00000403 13-Hydroxyoctadecadienoic acid Banks, A.; Keay, J. N.; Smith, J. G. M. Structure of conjugated methyl linoleate hydroperoxide. Nature (London, United Kingdom) (1957), 179 1078.