1.0 2016-09-30 23:18:00 UTC 2020-06-04 20:18:02 UTC BMDB0005474 BMDB05474 TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), also known as TG or 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol, 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(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is considered to be a triradylglycerol lipid molecule. TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) can be biosynthesized from DG(18:2(9Z,12Z)/18:2(9Z,12Z)/0:0) and linoleoyl-CoA through its interaction with the enzyme diacylglycerol O-acyltransferase. In cattle, TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) pathway. 1,2,3-Propanetriol trilinoleate 1,2,3-Propenetriol tri(9,12-octadecadienoate) 1,2,3-Tri-(9Z,12Z)-octadecadienoylglycerol 1,2,3-Tri-(9Z,12Z-octadecadienoyl)glycerol Glyceryl trilinoleate Linoleoyl triglyceride TAG(18:2/18:2/18:2) TAG(54:6) TG TG(18:2/18:2/18:2) TG(18:2Omega6/18:2omega6/18:2omega6) TG(54:6) Tracylglycerol(18:2omega6/18:2omega6/18:2omega6) Triacylglycerol(18:2/18:2/18:2) Triacylglycerol(54:6) Trilinolein 1,2,3-Propanetriol trilinoleic acid 1,2,3-Propenetriol tri(9,12-octadecadienoic acid) Glyceryl trilinoleic acid Trilinoleic glycerol Trilinolein, (all-e)-isomer Trilinoelaidate Glycerol trilinoleate Trilinoelaidin Triacylglycerol 1-linoleoyl-2-linoleoyl-3-linoleoyl-glycerol Tracylglycerol(18:2/18:2/18:2) Triglyceride TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) Tracylglycerol(54:6) 1-(9Z,12Z-octadecadienoyl)-2-(9Z,12Z-octadecadienoyl)-3-(9Z,12Z-octadecadienoyl)-glycerol TAG(18:2n6/18:2n6/18:2n6) TAG(18:2W6/18:2W6/18:2W6) TG(18:2n6/18:2n6/18:2n6) TG(18:2W6/18:2W6/18:2W6) Tracylglycerol(18:2n6/18:2n6/18:2n6) Tracylglycerol(18:2W6/18:2W6/18:2W6) C57H98O6 879.3844 878.736340868 1,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate triglyceride 537-40-6 [H]C(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C57H98O6/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/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27- HBOQXIRUPVQLKX-BBWANDEASA-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 triglyceride Solid logp 10.65 ALOGPS logs -8.05 ALOGPS logp 19.42 ChemAxon pka_strongest_basic -6.6 ChemAxon iupac 1,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate ChemAxon average_mass 879.3844 ChemAxon mono_mass 878.736340868 ChemAxon smiles [H]C(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C57H98O6 ChemAxon inchi InChI=1S/C57H98O6/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/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27- ChemAxon inchikey HBOQXIRUPVQLKX-BBWANDEASA-N ChemAxon polar_surface_area 78.9 ChemAxon refractivity 275.6 ChemAxon polarizability 113.22 ChemAxon rotatable_bond_count 50 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 De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) SMP0075380 Specdb::MsMs 627895 Specdb::MsMs 627896 Specdb::MsMs 627897 Specdb::MsMs 1468802 Specdb::MsMs 1468803 Specdb::MsMs 1468804 Specdb::MsMs 2547243 Specdb::MsMs 2547244 Specdb::MsMs 2547245 Specdb::MsMs 2677254 Specdb::MsMs 2677255 Specdb::MsMs 2677256 Specdb::MsMs 2753071 Specdb::MsMs 2753072 Specdb::MsMs 2753073 Specdb::MsMs 2922871 Specdb::MsMs 2922872 Specdb::MsMs 2922873 Specdb::MsMs 3028535 Specdb::MsMs 3028536 Specdb::MsMs 3028537 Milk 7.5 +/- 0.3 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 20 +/- 1 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 89 +/- 4 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 0.26 +/- 0.02 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 5322095 C00422 75844 4479674 FDB094336 Triacylglycerols 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)