1.0 2016-10-03 18:07:13 UTC 2020-06-04 20:26:10 UTC BMDB0010460 BMDB10460 TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] is considered to be a triradylglycerol lipid molecule. TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] can be biosynthesized from DG(18:1(9Z)/18:1(9Z)/0:0) and alpha-linolenoyl-CoA; which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))[iso3] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) pathway. 1-alpha-linolenoyl-2-oleoyl-3-oleoyl-glycerol TG(18:3/18:1/18:1) TG(18:3n3/18:1n9/18:1n9) TG(18:3w3/18:1w9/18:1w9) TG(54:5) Tag(18:3(9Z,12Z,15Z)/18:1(9Z)/18:1(9Z)) Tag(18:3/18:1/18:1) Tag(18:3n3/18:1n9/18:1n9) Tag(18:3w3/18:1w9/18:1w9) Tag(54:5) Triacylglycerol(18:3(9Z,12Z,15Z)/18:1(9Z)/18:1(9Z)) Triacylglycerol(18:3/18:1/18:1) Triacylglycerol(18:3n3/18:1n9/18:1n9) Triacylglycerol(18:3w3/18:1w9/18:1w9) Triacylglycerol(54:5) Triacylglycerol Triglyceride TG(18:3(9Z,12Z,15Z)/18:1(9Z)/18:1(9Z)) 1-Oleoyl-2-oleoyl-3-a-linolenoyl-glycerol 1-Oleoyl-2-oleoyl-3-alpha-linolenoyl-glycerol TAG(18:1/18:1/18:3) TAG(18:1n9/18:1n9/18:3n3) TAG(18:1W9/18:1W9/18:3W3) TG(18:1/18:1/18:3) TG(18:1n9/18:1n9/18:3n3) TG(18:1W9/18:1W9/18:3W3) Tracylglycerol(18:1/18:1/18:3) Tracylglycerol(18:1n9/18:1n9/18:3n3) Tracylglycerol(18:1W9/18:1W9/18:3W3) Tracylglycerol(54:5) C57H100O6 881.4003 880.751990932 (2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate (2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C57H100O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h7,10,16,19,25-30,54H,4-6,8-9,11-15,17-18,20-24,31-53H2,1-3H3/b10-7-,19-16-,28-25-,29-26-,30-27-/t54-/m0/s1 OEJXMJPFOHYSIU-GRLFFVHSSA-N belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Organic compounds Lipids and lipid-like molecules Glycerolipids Triradylcglycerols Triacylglycerols Carbonyl compounds Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Lineolic acids and derivatives Organic oxides Tricarboxylic acids and derivatives Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Hydrocarbon derivative Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Triacyl-sn-glycerol Tricarboxylic acid or derivatives Aliphatic acyclic compounds Triacylglycerols Solid logp 10.76 ALOGPS logs -8.15 ALOGPS logp 19.78 ChemAxon pka_strongest_basic -6.6 ChemAxon iupac (2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate ChemAxon average_mass 881.4003 ChemAxon mono_mass 880.751990932 ChemAxon smiles [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C57H100O6 ChemAxon inchi InChI=1S/C57H100O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h7,10,16,19,25-30,54H,4-6,8-9,11-15,17-18,20-24,31-53H2,1-3H3/b10-7-,19-16-,28-25-,29-26-,30-27-/t54-/m0/s1 ChemAxon inchikey OEJXMJPFOHYSIU-GRLFFVHSSA-N ChemAxon polar_surface_area 78.9 ChemAxon refractivity 274.48 ChemAxon polarizability 114.96 ChemAxon rotatable_bond_count 51 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 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 1457156 Specdb::MsMs 1457157 Specdb::MsMs 1457158 Specdb::MsMs 1468376 Specdb::MsMs 1468377 Specdb::MsMs 1468378 All Tissues 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 Milk 39 +/- 3 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 91 +/- 3 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 314 +/- 11 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 1.3 +/- 0.1 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 FDB094591 Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. 28965405 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)