1.0 2018-08-29 17:09:01 UTC 2020-06-04 20:15:37 UTC BMDB0062629 BMDB62629 DG(18:0/18:3(9Z,12Z,15Z)/0:0)[iso2] DG(18:0/18:3(9Z,12Z,15Z)/0:0), also known as diacylglycerol or DAG(18:0/18:3), 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. Thus, DG(18:0/18:3(9Z,12Z,15Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/18:3(9Z,12Z,15Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/18:3(9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:0/18:3(9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:0/18:3(9Z,12Z,15Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(18:0/18:3(9Z,12Z,15Z)/0:0) and eicosadienoyl-CoA can be converted into TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) through its interaction with the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(18:0/18:3(9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:0/18:3(9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(18:0/18:3(9Z,12Z,15Z)/0:0) and erucoyl-CoA can be converted into TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z)) through the action of the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(18:0/18:3(9Z,12Z,15Z)/0:0) can be biosynthesized from PA(18:0/18:3(9Z,12Z,15Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(18:0/18:3(9Z,12Z,15Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme diacylglycerol O-acyltransferase. In cattle, DG(18:0/18:3(9Z,12Z,15Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z)) pathway, de novo triacylglycerol biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z)) pathway, and de novo triacylglycerol biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway. C39H70O5 618.984 618.522325354 (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate [H][C@@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,37,40H,3-5,7,9-11,13,15-17,19,21-36H2,1-2H3/b8-6-,14-12-,20-18-/t37-/m1/s1 UBECYQFWKVVULW-JTIFTRAISA-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 1,2-diacylglycerols Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Organic oxides Primary alcohols 1,2-acyl-sn-glycerol Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Diacylglycerol Dicarboxylic acid or derivatives Diradylglycerol Fatty acid ester Glycerolipid Hydrocarbon derivative Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Aliphatic acyclic compounds logp 10.12 ALOGPS logs -7.74 ALOGPS logp 12.7 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate ChemAxon average_mass 618.984 ChemAxon mono_mass 618.522325354 ChemAxon smiles [H][C@@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC ChemAxon formula C39H70O5 ChemAxon inchi InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,12,14,18,20,37,40H,3-5,7,9-11,13,15-17,19,21-36H2,1-2H3/b8-6-,14-12-,20-18-/t37-/m1/s1 ChemAxon inchikey UBECYQFWKVVULW-JTIFTRAISA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 189.45 ChemAxon polarizability 80.36 ChemAxon rotatable_bond_count 35 ChemAxon acceptor_count 3 ChemAxon donor_count 1 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 1247449 Specdb::MsMs 1247450 Specdb::MsMs 1247451 Specdb::MsMs 1362778 Specdb::MsMs 1362779 Specdb::MsMs 1362780 Milk 12.9 +/- 0.2 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 32 +/- 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 69 +/- 1 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 1.16 +/- 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 102272272 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)