Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 22:10:36 UTC
Update Date2023-12-14 16:53:56 UTC
Metabolite IDMMDBc0056988
Metabolite Identification
Common NamePG(15:0cycw5/16:0)
DescriptionPG(15:0cycw5/16:0) 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(15:0cycw5/16:0), in particular, consists of one cis-9,10-Methylenetetradecanoic acid chain at the C-1 position and one hexadecanoyl 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-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-(hexadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinateGenerator
Molecular FormulaC37H71O10P
Average Mass706.939
Monoisotopic Mass706.478485484
IUPAC Name[(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-(hexadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name(2R)-3-{[8-(2-butylcyclopropyl)octanoyl]oxy}-2-(hexadecanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC1CC1CCCC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H71O10P/c1-3-5-7-8-9-10-11-12-13-14-15-18-22-26-37(41)47-35(31-46-48(42,43)45-29-34(39)28-38)30-44-36(40)25-21-19-16-17-20-24-33-27-32(33)23-6-4-2/h32-35,38-39H,3-31H2,1-2H3,(H,42,43)/t32?,33?,34-,35+/m0/s1
InChI KeyHOTXRZHWAKBPHX-ZZFZTORUSA-N