Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:49:36 UTC
Update Date2023-12-14 16:53:41 UTC
Metabolite IDMMDBc0056462
Metabolite Identification
Common NameCDP-DG(22:1(11Z)/28:1(11Z))
DescriptionCDP-DG(22:1(11Z)/28:1(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(22:1(11Z)/28:1(11Z)), in particular, consists of one 11Z-docosenoyl chain at the C-1 position and one 11Z-octacosanoyl 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(22:1(11Z)/28:1(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)-3-[(11Z)-docos-11-enoyloxy]-2-[(11Z)-octacos-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC62H113N3O15P2
Average Mass1202.54
Monoisotopic Mass1201.764693947
IUPAC Name{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-[(11Z)-docos-11-enoyloxy]-2-[(11Z)-octacos-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)-3-[(11Z)-docos-11-enoyloxy]-2-[(11Z)-octacos-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCCCCCC)(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/CCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C62H113N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-24-25-26-27-28-30-32-34-36-38-40-42-44-46-48-58(67)78-54(51-75-57(66)47-45-43-41-39-37-35-33-31-29-22-20-18-16-14-12-10-8-6-4-2)52-76-81(71,72)80-82(73,74)77-53-55-59(68)60(69)61(79-55)65-50-49-56(63)64-62(65)70/h22,28-30,49-50,54-55,59-61,68-69H,3-21,23-27,31-48,51-53H2,1-2H3,(H,71,72)(H,73,74)(H2,63,64,70)/b29-22-,30-28-/t54-,55-,59-,60-,61-/m1/s1
InChI KeyGTOKXARCBHOTCY-IIJNQXEHSA-N