Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:48:39 UTC
Update Date2023-12-14 16:53:40 UTC
Metabolite IDMMDBc0056439
Metabolite Identification
Common NameCDP-DG(16:1(11Z)/22:1(11Z))
DescriptionCDP-DG(16:1(11Z)/22:1(11Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. 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. CDP-DG(16:1(11Z)/22:1(11Z)), in particular, consists of one 11Z-hexadecenoyl chain at the C-1 position and one 11Z-docosenoyl chain at the C-2 position. In E. coli glycerophospholipid metabolism, the biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(16:1(11Z)/22:1(11Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.
Structure
Synonyms
ValueSource
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-2-[(11Z)-docos-11-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC50H89N3O15P2
Average Mass1034.216
Monoisotopic Mass1033.576893174
IUPAC Name{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-[(11Z)-docos-11-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
Traditional Name[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-[(11Z)-docos-11-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC\C=C/CCCCCCCCCC
InChI Identifier
InChI=1S/C50H89N3O15P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2)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/h10,12,19-20,37-38,42-43,47-49,56-57H,3-9,11,13-18,21-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b12-10-,20-19-/t42-,43-,47-,48-,49-/m1/s1
InChI KeyOGFYFIJCWFWINV-ONUHDAGWSA-N