1.0 2018-09-23 03:10:41 UTC 2020-06-04 19:33:23 UTC BMDB0063598 BMDB63598 DG(O-16:0/20:4(8E,11E,14E,17E)/0:0) DG(O-16:0/20:4(8E,11E,14E,17E)/0:0), also referred to as DG(20:4), is a diglyceride which belongs to the family of Diacylglycerols (DAGs). These are glycerolipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. DAGs can have many different combinations of fatty acids attached at the C-1, C-2, or C-3 positions. DG(20:4), in particular, consists of one chain of hexadecyl acid at the C-1 position and one chain of arachidonic acid at the C-2 position. DG(20:4) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-3 position. C39H70O4 602.985 602.527410734 (2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate (2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate [H][C@@](CO)(COCCCCCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC InChI=1S/C39H70O4/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-39(41)43-38(36-40)37-42-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,38,40H,3-4,6,8-10,12,14-16,18,20,23-37H2,1-2H3/b7-5-,13-11-,19-17-,22-21-/t38-/m1/s1 ZOQPRIBCWWPWEH-SCBZKDMTSA-N belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively. Organic compounds Lipids and lipid-like molecules Glycerolipids Diradylglycerols 1-alkyl,2-acylglycerols Carbonyl compounds Carboxylic acid esters Dialkyl ethers Fatty acid esters Glycerol ethers Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Primary alcohols 1-alkyl,2-acylglycerol Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Ether Fatty acid ester Fatty acyl Glycerol ether Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Aliphatic acyclic compounds logp 10.28 ALOGPS logs -7.57 ALOGPS logp 12.71 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate ChemAxon average_mass 602.985 ChemAxon mono_mass 602.527410734 ChemAxon smiles [H][C@@](CO)(COCCCCCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC ChemAxon formula C39H70O4 ChemAxon inchi InChI=1S/C39H70O4/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-39(41)43-38(36-40)37-42-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,38,40H,3-4,6,8-10,12,14-16,18,20,23-37H2,1-2H3/b7-5-,13-11-,19-17-,22-21-/t38-/m1/s1 ChemAxon inchikey ZOQPRIBCWWPWEH-SCBZKDMTSA-N ChemAxon polar_surface_area 55.76 ChemAxon refractivity 190.81 ChemAxon polarizability 79.23 ChemAxon rotatable_bond_count 34 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 1220110 Specdb::MsMs 1220111 Specdb::MsMs 1220112 Specdb::MsMs 1335802 Specdb::MsMs 1335803 Specdb::MsMs 1335804 Milk 0.70 +/- 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 FDB097600 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)