Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 22:12:34 UTC
Update Date2023-12-14 16:53:58 UTC
Metabolite IDMMDBc0057037
Metabolite Identification
Common NamePGP(17:0cycw7/19:0cycw7)
DescriptionPGP(17:0cycw7/19:0cycw7) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. 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. PGP(17:0cycw7/19:0cycw7), in particular, consists of one heptadec-9-10-cyclo-anoyl chain at the C-1 position and one heptadec-11-12-cyclo-anoyl 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. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. In E. coli, PGPs can be found in the cytoplasmic membrane.
Structure
SynonymsNot Available
Molecular FormulaC42H80O13P2
Average Mass855.037
Monoisotopic Mass854.507416632
IUPAC Name[(2S)-3-({[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2S)-3-{[(2R)-2-{[10-(2-hexylcyclopropyl)decanoyl]oxy}-3-{[8-(2-hexylcyclopropyl)octanoyl]oxy}propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCCCC)OC(=O)CCCCCCCCCC1CC1CCCCCC
InChI Identifier
InChI=1S/C42H80O13P2/c1-3-5-7-17-23-35-29-37(35)25-19-13-10-9-11-15-22-28-42(45)55-40(34-54-57(49,50)53-32-39(43)31-52-56(46,47)48)33-51-41(44)27-21-16-12-14-20-26-38-30-36(38)24-18-8-6-4-2/h35-40,43H,3-34H2,1-2H3,(H,49,50)(H2,46,47,48)/t35?,36?,37?,38?,39-,40+/m0/s1
InChI KeyIOQCYOCDLMYJIX-ZKSHJAJDSA-N