1.0 2018-08-29 17:08:57 UTC 2020-06-04 20:15:36 UTC BMDB0062625 BMDB62625 DG(16:1(9Z)/20:2(11Z,14Z)/0:0)[iso2] DG(16:1(9Z)/20:2(11Z,14Z)/0:0), also known as diacylglycerol or DAG(16:1/20:2), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/20:2(11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/20:2(11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and meadoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)); which is mediated by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and docosanoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/22:0); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:2(11Z,14Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Finally, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) and docosadienoyl-CoA can be converted into TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) through the action of the enzyme diacylglycerol O-acyltransferase. In cattle, DG(16:1(9Z)/20:2(11Z,14Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0) pathway, and de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z)) pathway. (2R)-1-[(9Z)-Hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z,14Z)-icosa-11,14-dienoic acid C39H70O5 618.984 618.522325354 (2R)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z,14Z)-icosa-11,14-dienoate (2R)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z,14Z)-icosa-11,14-dienoate [H][C@@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,37,40H,3-10,12,15,19-36H2,1-2H3/b13-11-,16-14-,18-17-/t37-/m1/s1 WPAJXHHVSWVZKN-DFCPKGTFSA-N belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Organic compounds Lipids and lipid-like molecules Glycerolipids Diradylglycerols 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 Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Aliphatic acyclic compounds logp 10.05 ALOGPS logs -7.74 ALOGPS logp 12.7 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (11Z,14Z)-icosa-11,14-dienoate ChemAxon average_mass 618.984 ChemAxon mono_mass 618.522325354 ChemAxon smiles [H][C@@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC ChemAxon formula C39H70O5 ChemAxon inchi InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h11,13-14,16-18,37,40H,3-10,12,15,19-36H2,1-2H3/b13-11-,16-14-,18-17-/t37-/m1/s1 ChemAxon inchikey WPAJXHHVSWVZKN-DFCPKGTFSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 189.45 ChemAxon polarizability 80.33 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 1242922 Specdb::MsMs 1242923 Specdb::MsMs 1242924 Specdb::MsMs 1358311 Specdb::MsMs 1358312 Specdb::MsMs 1358313 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 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)