Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:48:43 UTC
Update Date2023-12-14 16:53:40 UTC
Metabolite IDMMDBc0056441
Metabolite Identification
Common NameCDP-DG(16:1(9Z)/12:0(3-OH))
DescriptionCDP-DG(16:1(9Z)/12:0(3-OH)) 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(9Z)/12:0(3-OH)), in particular, consists of one 9Z-hexadecenoyl chain at the C-1 position and one 3-hydroxydodecanoyl 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(9Z)/12:0(3-OH)) 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-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)phosphinateGenerator
Molecular FormulaC40H71N3O16P2
Average Mass911.961
Monoisotopic Mass911.430957214
IUPAC Name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydodecanoyl)oxy]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-[(9Z)-hexadec-9-enoyloxy]-2-[(3-hydroxydodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CC(O)CCCCCCCCC
InChI Identifier
InChI=1S/C40H71N3O16P2/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-35(45)54-28-32(57-36(46)27-31(44)23-21-19-17-10-8-6-4-2)29-55-60(50,51)59-61(52,53)56-30-33-37(47)38(48)39(58-33)43-26-25-34(41)42-40(43)49/h12-13,25-26,31-33,37-39,44,47-48H,3-11,14-24,27-30H2,1-2H3,(H,50,51)(H,52,53)(H2,41,42,49)/b13-12-/t31?,32-,33-,37+,38?,39-/m1/s1
InChI KeyMQVKLSSWJTULLQ-UDBKSRFUSA-N