Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 13:00:20 UTC
Update Date2022-09-01 00:20:56 UTC
Metabolite IDMMDBc0044423
Metabolite Identification
Common NameCDP-DG(22:1(13Z)/23:1(9Z))
DescriptionCDP-DG(22:1(13Z)/23:1(9Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. CDP-DG(22:1(13Z)/23:1(9Z)), in particular, consists of two 13Z-docosenoyl chain at positions C-1 and C2. 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(13Z)/23:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.
Structure
Synonyms
ValueSource
{[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-tricos-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC57H103N3O15P2
Average Mass1132.405
Monoisotopic Mass1131.686443625
IUPAC Name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-tricos-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
Traditional Name[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(9Z)-tricos-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C57H103N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-43-53(62)73-49(46-70-52(61)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)47-71-76(66,67)75-77(68,69)72-48-50-54(63)55(64)56(74-50)60-45-44-51(58)59-57(60)65/h18,20,27,29,44-45,49-50,54-56,63-64H,3-17,19,21-26,28,30-43,46-48H2,1-2H3,(H,66,67)(H,68,69)(H2,58,59,65)/b20-18-,29-27-/t49-,50-,54+,55?,56-/m1/s1
InChI KeyKSFPZQHUYSHLEV-BXUUSWPFSA-N