Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:49:48 UTC
Update Date2023-02-07 23:27:17 UTC
Metabolite IDMMDBc0031454
Metabolite Identification
Common NamePG(18:1(9Z)/12:0(3-OH))
DescriptionPG(12:0(3-OH)/18:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(12:0(3-OH)/18:1(9Z)), in particular, consists of one 3-hydroxydodecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
Structure
SynonymsNot Available
Molecular FormulaC36H69O11P
Average Mass708.911
Monoisotopic Mass708.45775004
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy((2R)-2-[(3-hydroxydodecanoyl)oxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC(O)CCCCCCCCC
InChI Identifier
InChI=1S/C36H69O11P/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-24-26-35(40)44-30-34(31-46-48(42,43)45-29-33(39)28-37)47-36(41)27-32(38)25-23-21-19-10-8-6-4-2/h14-15,32-34,37-39H,3-13,16-31H2,1-2H3,(H,42,43)/b15-14-/t32?,33-,34+/m0/s1
InChI KeyJBYOWJPVFJCYBW-IQAYTRFVSA-N