Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:49:09 UTC
Update Date2023-12-14 16:53:40 UTC
Metabolite IDMMDBc0056453
Metabolite Identification
Common NameCDP-DG(20:1(13Z)/22:1(11Z))
DescriptionCDP-DG(20:1(13Z)/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(20:1(13Z)/22:1(11Z)), in particular, consists of one 13Z-eicosenoyl 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(20:1(13Z)/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-[(13Z)-icos-13-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC54H97N3O15P2
Average Mass1090.324
Monoisotopic Mass1089.639493431
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-[(13Z)-icos-13-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-[(13Z)-icos-13-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCC)(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/C54H97N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-50(59)70-46(43-67-49(58)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2)44-68-73(63,64)72-74(65,66)69-45-47-51(60)52(61)53(71-47)57-42-41-48(55)56-54(57)62/h14,16,21-22,41-42,46-47,51-53,60-61H,3-13,15,17-20,23-40,43-45H2,1-2H3,(H,63,64)(H,65,66)(H2,55,56,62)/b16-14-,22-21-/t46-,47-,51-,52-,53-/m1/s1
InChI KeyHZBOBRKGFMWKFI-JOSDHKMXSA-N