Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 22:09:50 UTC
Update Date2023-12-14 16:53:56 UTC
Metabolite IDMMDBc0056971
Metabolite Identification
Common NamePG(10:0/15:0)
DescriptionPG(10:0/15:0) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(10:0/15:0), in particular, consists of one decanoyl chain at the C-1 position and one pentadecanoyl chain at the C-2 position. Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Structure
Synonyms
ValueSource
[(2R)-3-(Decanoyloxy)-2-(pentadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinateGenerator
Molecular FormulaC31H61O10P
Average Mass624.793
Monoisotopic Mass624.400235162
IUPAC Name[(2R)-3-(decanoyloxy)-2-(pentadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name(2R)-3-(decanoyloxy)-2-(pentadecanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C31H61O10P/c1-3-5-7-9-11-12-13-14-15-17-19-21-23-31(35)41-29(27-40-42(36,37)39-25-28(33)24-32)26-38-30(34)22-20-18-16-10-8-6-4-2/h28-29,32-33H,3-27H2,1-2H3,(H,36,37)/t28-,29+/m0/s1
InChI KeyJSGDAYOFCMVAPW-URLMMPGGSA-N