1.0 2011-09-21 00:45:25 UTC 2015-07-21 06:58:07 UTC FDB024521 DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0) DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:4(6Z,9Z,12Z,15Z)/14:1(9Z)/0:0), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of myristoleic acid at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the myristoleic acid moiety is derived from milk fats. 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. 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-2 position. [HMDB] 1-stearidonoyl-2-myristoleoyl-sn-glycerol DAG(18:4/14:1) DAG(18:4n3/14:1n5) DAG(18:4w3/14:1w5) DG(18:4/14:1) DG(18:4n3/14:1n5) DG(18:4w3/14:1w5) Diacylglycerol(18:4/14:1) Diacylglycerol(18:4n3/14:1n5) Diacylglycerol(18:4w3/14:1w5) C35H58O5 558.832 558.428424966 (2S)-3-hydroxy-2-(tetradec-9-enoyloxy)propyl octadeca-6,9,12,15-tetraenoate (2S)-3-hydroxy-2-(tetradec-9-enoyloxy)propyl octadeca-6,9,12,15-tetraenoate [H][C@](CO)(COC(=O)CCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCCCC InChI=1S/C35H58O5/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,20-21,33,36H,3-4,6,8-9,14-15,18-19,22-32H2,1-2H3/t33-/m0/s1 DJPSDNJBZWPDDE-XIFFEERXSA-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. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic acyclic compounds 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 Solid logp 8.11 ALOGPS logs -7.28 ALOGPS solubility 2.91e-05 g/l ALOGPS logp 10.19 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-3-hydroxy-2-(tetradec-9-enoyloxy)propyl octadeca-6,9,12,15-tetraenoate ChemAxon average_mass 558.832 ChemAxon mono_mass 558.428424966 ChemAxon smiles [H][C@](CO)(COC(=O)CCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCCCC ChemAxon formula C35H58O5 ChemAxon inchi InChI=1S/C35H58O5/c1-3-5-7-9-11-13-15-16-17-18-20-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,20-21,33,36H,3-4,6,8-9,14-15,18-19,22-32H2,1-2H3/t33-/m0/s1 ChemAxon inchikey DJPSDNJBZWPDDE-XIFFEERXSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 173.28 ChemAxon polarizability 69.78 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB07328 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 2-acylglycerol O-acyltransferase 1 Q96PD6 MOGAT1 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 2-acylglycerol O-acyltransferase 3 Q86VF5 MOGAT3 Acyl-CoA wax alcohol acyltransferase 1 Q58HT5 AWAT1 Acyl-CoA wax alcohol acyltransferase 2 Q6E213 AWAT2 CDC42 binding protein kinase beta (DMPK-like) A9JR72 CDC42BPB CDC42-binding protein kinase beta Q8IWQ7 CDC42BPA Choline-phosphate cytidylyltransferase A P49585 PCYT1A Diacylglycerol O-acyltransferase 1 O75907 DGAT1 Diacylglycerol O-acyltransferase 2 Q96PD7 DGAT2 Diacylglycerol O-acyltransferase 2-like protein 6 Q6ZPD8 DGAT2L6 Endothelial lipase Q9Y5X9 LIPG Galactosylceramide sulfotransferase Q99999 GAL3ST1 Gastric triacylglycerol lipase P07098 LIPF Hepatic triacylglycerol lipase P11150 LIPC Inactive pancreatic lipase-related protein 1 P54315 PNLIPRP1 Kinase suppressor of Ras 1 Q8IVT5 KSR1 Kinase suppressor of Ras 2 Q6VAB6 KSR2 Lipoprotein lipase P06858 LPL Pancreatic lipase-related protein 2 P54317 PNLIPRP2 Pancreatic lipase-related protein 3 Q17RR3 PNLIPRP3 Pancreatic triacylglycerol lipase P16233 PNLIP Patatin-like phospholipase domain-containing protein 2 Q96AD5 PNPLA2 Patatin-like phospholipase domain-containing protein 3 Q9NST1 PNPLA3 Patatin-like phospholipase domain-containing protein 4 P41247 PNPLA4 Phosphatidate cytidylyltransferase 2 O95674 CDS2 Phosphatidylcholine:ceramide cholinephosphotransferase 1 Q86VZ5 SGMS1 Phosphatidylcholine:ceramide cholinephosphotransferase 2 Q8NHU3 SGMS2 Putative diacylglycerol O-acyltransferase 2-like protein 7 Q6IED9 DGAT2L7 Tensin-like C1 domain-containing phosphatase Q63HR2 TENC1