1.0 2011-09-21 00:41:11 UTC 2015-07-21 06:58:01 UTC FDB024193 CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) 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(9Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the arachidonic acid moiety is derived from animal fats and eggs. 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-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-CDP 1-Oleoyl-2-arachidonoyl-sn-glycero-3-cytidine-5'-diate 1-oleoyl-2-arachidonoyl-sn-glycero-3-cytidine-5'-diphosphate CDP-DG(18:1n9/20:4n6) CDP-DG(18:1w9/20:4w6) CDP-Diacylglycerol(18:1n9/20:4n6) CDP-Diacylglycerol(18:1w9/20:4w6) C50H83N3O15P2 1028.1526 1027.529942025 {[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(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)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-enoyloxy)propoxy)phosphoryl]oxy)phosphinic acid [H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(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)CCCC=CCC=CCC=CCC=CCCCCC InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h11,13,17-19,21-22,24,28,30,37-38,42-43,47-49,56-57H,3-10,12,14-16,20,23,25-27,29,31-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t42-,43-,47+,48?,49-/m1/s1 JHMUAQLWUZUICD-HKRBFXDCSA-N belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages. Phosphatidylethanolamines Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoethanolamines Aliphatic acyclic compounds Amino acids and derivatives Carbonyl compounds Carboxylic acid esters Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Phosphoethanolamines Aliphatic acyclic compound Alkyl phosphate Amine Amino acid or derivatives Carbonyl group Carboxylic acid derivative Carboxylic acid ester Diacylglycero-3-phosphoethanolamine Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphoethanolamine Phosphoric acid ester Primary aliphatic amine Primary amine Solid logp 7.13 ALOGPS logs -5.65 ALOGPS solubility 2.29e-03 g/l ALOGPS logp 10.49 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)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1028.1526 ChemAxon mono_mass 1027.529942025 ChemAxon smiles [H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(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)CCCC=CCC=CCC=CCC=CCCCCC ChemAxon formula C50H83N3O15P2 ChemAxon inchi InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h11,13,17-19,21-22,24,28,30,37-38,42-43,47-49,56-57H,3-10,12,14-16,20,23,25-27,29,31-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t42-,43-,47+,48?,49-/m1/s1 ChemAxon inchikey JHMUAQLWUZUICD-HKRBFXDCSA-N ChemAxon polar_surface_area 264.26 ChemAxon refractivity 284.81 ChemAxon polarizability 110.85 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB06999 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