1.0 2011-09-21 00:41:00 UTC 2015-07-21 06:58:01 UTC FDB024183 CDP-DG(18:1(11Z)/18:1(9Z)) CDP-DG(18:1(11Z)/18:1(9Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(18:1(11Z)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05% or so of the total phospholipids. [HMDB] 1-(11Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-CDP 1-Vaccenoyl-2-oleoyl-sn-glycero-3-cytidine-5'-diate 1-vaccenoyl-2-oleoyl-sn-glycero-3-cytidine-5'-diphosphate CDP-DG(18:1n7/18:1n9) CDP-DG(18:1w7/18:1w9) CDP-Diacylglycerol(18:1n7/18:1n9) CDP-Diacylglycerol(18:1w7/18:1w9) C48H85N3O15P2 1006.1471 1005.545592089 {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid [(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy([hydroxy((2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@]([H])(C(O)[C@@]1([H])O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC=CCCCCCCCC InChI=1S/C48H85N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h13,15,18,20,35-36,40-41,45-47,54-55H,3-12,14,16-17,19,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/t40-,41-,45+,46?,47-/m1/s1 MJTZWNDRIHJESM-KTSAPKHVSA-N belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. CDP-diacylglycerols Organic compounds Lipids and lipid-like molecules Glycerophospholipids CDP-glycerols Aromatic heteromonocyclic compounds 1,2-diols Amino acids and derivatives Aminopyrimidines and derivatives Azacyclic compounds Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Fatty acid esters Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Imidolactams Monoalkyl phosphates Monosaccharide phosphates Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Pyrimidine ribonucleoside diphosphates Pyrimidones Pyrophosphatidic acids Secondary alcohols Tetrahydrofurans 1,2-diol Alcohol Alkyl phosphate Amine Amino acid or derivatives Aminopyrimidine Aromatic heteromonocyclic compound Azacycle Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cdp-diacylglycerol Diacyl-glycerol-3-pyrophosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Pyrimidine Pyrimidine ribonucleoside diphosphate Pyrimidone Secondary alcohol Tetrahydrofuran Solid logp 6.97 ALOGPS logs -5.48 ALOGPS solubility 3.31e-03 g/l ALOGPS logp 10.69 ChemAxon pka_strongest_acidic 2.55 ChemAxon pka_strongest_basic 1.78 ChemAxon iupac {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1006.1471 ChemAxon mono_mass 1005.545592089 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@]([H])(C(O)[C@@]1([H])O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC=CCCCCCCCC ChemAxon formula C48H85N3O15P2 ChemAxon inchi InChI=1S/C48H85N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h13,15,18,20,35-36,40-41,45-47,54-55H,3-12,14,16-17,19,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/t40-,41-,45+,46?,47-/m1/s1 ChemAxon inchikey MJTZWNDRIHJESM-KTSAPKHVSA-N ChemAxon polar_surface_area 264.26 ChemAxon refractivity 272.26 ChemAxon polarizability 110.89 ChemAxon rotatable_bond_count 44 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB06989 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 Phosphatidate cytidylyltransferase 2 O95674 CDS2