1.0 2016-09-30 23:23:13 UTC 2020-06-04 20:30:58 UTC BMDB0006547 BMDB06547 Stearidonic acid Stearidonic acid, also known as stearidonate, 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. Stearidonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Stearidonic acid participates in a number of enzymatic reactions, within cattle. In particular, Stearidonic acid can be biosynthesized from alpha-linolenic acid through its interaction with the enzyme fatty acid desaturase 2. In addition, Stearidonic acid can be converted into cis-8,11,14,17-eicosatetraenoic acid through the action of the enzyme elongation OF very long chain fatty acids protein 5. In cattle, stearidonic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. Stearidonate 6,9,12,15-Octadecatetraenoate C18H28O2 276.42 276.208930142 (6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid (6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid [H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCC(O)=O InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+,13-12+ JIWBIWFOSCKQMA-GFRMADBLSA-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 Long-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Aliphatic acyclic compounds Unsaturated fatty acids Solid logp 6.19 ALOGPS logs -5.74 ALOGPS logp 5.7 ChemAxon pka_strongest_acidic 4.92 ChemAxon iupac (6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid ChemAxon average_mass 276.42 ChemAxon mono_mass 276.208930142 ChemAxon smiles [H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCC(O)=O ChemAxon formula C18H28O2 ChemAxon inchi InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+,13-12+ ChemAxon inchikey JIWBIWFOSCKQMA-GFRMADBLSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 90.75 ChemAxon polarizability 34.16 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 2 ChemAxon donor_count 1 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::MsMs 1322287 Specdb::MsMs 1322288 Specdb::MsMs 1322289 Specdb::MsMs 1436656 Specdb::MsMs 1436657 Specdb::MsMs 1436658 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 Milk 1230.0390 +/- 506.487 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Milk 1049.151 +/- 361.776 uM The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189 Oocyte Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries. McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70. 10793638 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 5282837 Stearidonic acid M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189