Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:48:29 UTC
Update Date2023-12-14 16:53:40 UTC
Metabolite IDMMDBc0056434
Metabolite Identification
Common NameCDP-DG(15:0cycw5/16:1(9Z))
DescriptionCDP-DG(15:0cycw5/16:1(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(15:0cycw5/16:1(9Z)), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain at the C-1 position and one 9Z-hexadecenoyl 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(15:0cycw5/16:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.
Structure
Synonyms
ValueSource
({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(9Z)-hexadec-9-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)({[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinateGenerator
Molecular FormulaC43H75N3O15P2
Average Mass936.027
Monoisotopic Mass935.467342723
IUPAC Name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(9Z)-hexadec-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-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-[(9Z)-hexadec-9-enoyloxy]propoxy(hydroxy)phosphoryl]oxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCC1CC1CCCC)(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/CCCCCC
InChI Identifier
InChI=1S/C43H75N3O15P2/c1-3-5-7-8-9-10-11-12-13-14-15-18-22-26-39(48)59-35(30-56-38(47)25-21-19-16-17-20-24-34-29-33(34)23-6-4-2)31-57-62(52,53)61-63(54,55)58-32-36-40(49)41(50)42(60-36)46-28-27-37(44)45-43(46)51/h10-11,27-28,33-36,40-42,49-50H,3-9,12-26,29-32H2,1-2H3,(H,52,53)(H,54,55)(H2,44,45,51)/b11-10-/t33?,34?,35-,36-,40+,41?,42-/m1/s1
InChI KeyLDVCQLGLCYNXHR-BTOUTPBHSA-N