Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:51:16 UTC
Update Date2023-02-07 22:11:08 UTC
Metabolite IDMMDBc0031492
Metabolite Identification
Common NamePG(12:0(3-OH)/16:1(9Z))
DescriptionPG(16:1(9Z)/12:0(3-OH)) 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(16:1(9Z)/12:0(3-OH)), in particular, consists of one 9Z-hexadecenoyl chain to the C-1 atom, and one 3-hydroxydodecanoyl 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 FormulaC34H65O11P
Average Mass680.857
Monoisotopic Mass680.426449911
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(3-hydroxydodecanoyl)oxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C34H65O11P/c1-3-5-7-9-11-12-13-14-15-16-18-20-22-24-33(38)45-32(29-44-46(40,41)43-27-31(37)26-35)28-42-34(39)25-30(36)23-21-19-17-10-8-6-4-2/h12-13,30-32,35-37H,3-11,14-29H2,1-2H3,(H,40,41)/b13-12-/t30?,31-,32+/m0/s1
InChI KeyDYLWWUHLOZGLPM-KVRHGVBDSA-N