1.0 2011-09-21 00:41:05 UTC 2015-07-21 06:58:01 UTC FDB024186 CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 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)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the eicsoatetraenoic acid moiety is derived from fish oils. 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-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-CDP 1-Vaccenoyl-2-eicsoate 1-Vaccenoyl-2-eicsoatetraenoyl-sn-glycero-3-cytidine-5'-diate 1-vaccenoyl-2-eicsoatetraenoyl-sn-glycero-3-cytidine-5'-diphosphate 1-Vaccenoyl-2-eicsoic acid CDP-DG(18:1n7/20:4n3) CDP-DG(18:1w7/20:4w3) CDP-Diacylglycerol(18:1n7/20:4n3) CDP-Diacylglycerol(18:1w7/20:4w3) 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-8,11,14,17-tetraenoyloxy)-3-(octadec-11-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-8,11,14,17-tetraenoyloxy)-3-(octadec-11-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)CCCCCCC=CCC=CCC=CCC=CCC 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/h5,7,11,13-14,16-17,19,22,24,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,15,18,20-21,23,25-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t42-,43-,47+,48?,49-/m1/s1 POTUYISZWXOXIP-HKRBFXDCSA-N belongs to the class of organic compounds known as phosphatidylinositols. These are glycerophosphoinositols where the glycerol is esterified with two fatty acids. Phosphatidylinositols Organic compounds Lipids and lipid-like molecules Glycerophospholipids Glycerophosphoinositols Aliphatic homomonocyclic compounds Carbonyl compounds Carboxylic acid esters Cyclohexanols Dialkyl phosphates Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Inositol phosphates Organic oxides Polyols Alcohol Aliphatic homomonocyclic compound Alkyl phosphate Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclitol or derivatives Cyclohexanol Diacylglycerophosphoinositol Dialkyl phosphate Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Inositol phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organooxygen compound Phosphoric acid ester Polyol Secondary alcohol Solid logp 7.08 ALOGPS logs -5.69 ALOGPS solubility 2.09e-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-8,11,14,17-tetraenoyloxy)-3-(octadec-11-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid ChemAxon average_mass 1028.1526 ChemAxon mono_mass 1027.529942025 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)CCCCCCC=CCC=CCC=CCC=CCC 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/h5,7,11,13-14,16-17,19,22,24,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,15,18,20-21,23,25-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t42-,43-,47+,48?,49-/m1/s1 ChemAxon inchikey POTUYISZWXOXIP-HKRBFXDCSA-N ChemAxon polar_surface_area 264.26 ChemAxon refractivity 284.81 ChemAxon polarizability 112.68 ChemAxon rotatable_bond_count 43 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon HMDB06992 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