Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:49:31 UTC
Update Date2023-12-14 16:53:41 UTC
Metabolite IDMMDBc0056460
Metabolite Identification
Common NameCDP-DG(22:1(11Z)/26:1(9Z))
DescriptionCDP-DG(22:1(11Z)/26:1(9Z)) 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)/26:1(9Z)), in particular, consists of one 11Z-docosenoyl chain at the C-1 position and one 9Z-hexacosenoyl 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)/26:1(9Z)) 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-[(9Z)-hexacos-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC60H109N3O15P2
Average Mass1174.486
Monoisotopic Mass1173.733393818
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-[(9Z)-hexacos-9-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-[(9Z)-hexacos-9-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)CCCCCCC\C=C/CCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C60H109N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-24-25-26-28-30-32-34-36-38-40-42-44-46-56(65)76-52(49-73-55(64)45-43-41-39-37-35-33-31-29-27-22-20-18-16-14-12-10-8-6-4-2)50-74-79(69,70)78-80(71,72)75-51-53-57(66)58(67)59(77-53)63-48-47-54(61)62-60(63)68/h22,27,30,32,47-48,52-53,57-59,66-67H,3-21,23-26,28-29,31,33-46,49-51H2,1-2H3,(H,69,70)(H,71,72)(H2,61,62,68)/b27-22-,32-30-/t52-,53-,57-,58-,59-/m1/s1
InChI KeyQAFLCIWXRPOWDD-IBNFQYTMSA-N