Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 14:49:43 UTC
Update Date2022-09-01 01:35:50 UTC
Metabolite IDMMDBc0046707
Metabolite Identification
Common NamePG(16:0/28:1(9Z))
DescriptionPG(16:0/28:1(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(16:0/28:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octocosanoyl 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
Synonyms
ValueSource
[(2S)-2,3-Dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(10Z)-octacos-10-enoyloxy]propoxy]phosphinateGenerator
Molecular FormulaC50H97O10P
Average Mass889.29
Monoisotopic Mass888.681936321
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-[(10Z)-octacos-10-enoyloxy]propoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-[(10Z)-octacos-10-enoyloxy]propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCC\C=C/CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C50H97O10P/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-42-50(54)60-48(46-59-61(55,56)58-44-47(52)43-51)45-57-49(53)41-39-37-35-33-31-29-16-14-12-10-8-6-4-2/h26-27,47-48,51-52H,3-25,28-46H2,1-2H3,(H,55,56)/b27-26-/t47-,48+/m0/s1
InChI KeyXBUAQLGBVVZDKA-QGSOGAJFSA-N