1.0 2018-08-29 17:09:02 UTC 2020-06-04 20:14:26 UTC BMDB0062630 BMDB62630 DG(18:0/20:0/0:0)[iso2] DG(18:0/20:0/0:0), also known as DAG(18:0/20:0) or diacylglycerol(38:0), 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(18:0/20:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/20:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/20:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:0/20:0/0:0) can be biosynthesized from PA(18:0/20:0) through the action of the enzyme phosphatidate phosphatase. Furthermore, DG(18:0/20:0/0:0) and eicosanoyl-CoA can be converted into TG(18:0/20:0/20:0)[iso3] through the action of the enzyme diacylglycerol O-acyltransferase. Furthermore, DG(18:0/20:0/0:0) can be biosynthesized from PA(18:0/20:0); which is mediated by the enzyme phosphatidate phosphatase. Finally, DG(18:0/20:0/0:0) and arachidonyl-CoA can be converted into TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z))[iso6]; which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(18:0/20:0/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:0/20:0/20:0) pathway and de novo triacylglycerol biosynthesis TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z)) pathway. C41H80O5 653.086 652.600575676 (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl icosanoate (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl icosanoate [H][C@@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC InChI=1S/C41H80O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h39,42H,3-38H2,1-2H3/t39-/m1/s1 JPKVDETWOQEHQO-LDLOPFEMSA-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 10.51 ALOGPS logs -7.63 ALOGPS logp 14.67 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl icosanoate ChemAxon average_mass 653.086 ChemAxon mono_mass 652.600575676 ChemAxon smiles [H][C@@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC ChemAxon formula C41H80O5 ChemAxon inchi InChI=1S/C41H80O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h39,42H,3-38H2,1-2H3/t39-/m1/s1 ChemAxon inchikey JPKVDETWOQEHQO-LDLOPFEMSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 195.3 ChemAxon polarizability 88.95 ChemAxon rotatable_bond_count 40 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::NmrOneD 264528 Specdb::NmrOneD 264529 Specdb::NmrOneD 264530 Specdb::NmrOneD 264531 Specdb::NmrOneD 264532 Specdb::NmrOneD 264533 Specdb::NmrOneD 264534 Specdb::NmrOneD 264535 Specdb::NmrOneD 264536 Specdb::NmrOneD 264537 Specdb::NmrOneD 264538 Specdb::NmrOneD 264539 Specdb::NmrOneD 264540 Specdb::NmrOneD 264541 Specdb::NmrOneD 264542 Specdb::NmrOneD 264543 Specdb::NmrOneD 264544 Specdb::NmrOneD 264545 Specdb::NmrOneD 264546 Specdb::NmrOneD 264547 Specdb::CMs 1084010 Specdb::MsMs 184650 Milk 6.1 +/- 0.1 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 38 +/- 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 57 +/- 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 1.6 +/- 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 101858606 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)