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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-09-25 13:33:46 UTC
Update Date2022-11-30 19:03:54 UTC
HMDB IDHMDB0010570
Secondary Accession Numbers
  • HMDB10570
Metabolite Identification
Common NamePG(16:0/16:0)
DescriptionPG(16:0/16:0) 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(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). 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. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.
Structure
Data?1657844036
Synonyms
ValueSource
1,2-Dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
1,2-DihexadecanoylphosphatidylglycerolChEBI
1,2-DipalmitoylphosphatidylglycerolChEBI
DihexadecanoylphosphatidylglycerolChEBI
DipalmitoylphosphatidylglycerolChEBI
GPG(16:0/16:0)ChEBI
GPG(32:0)ChEBI
PG(32:0)ChEBI
Phosphatidylglycerol(16:0/16:0)ChEBI
Phosphatidylglycerol(32:0)ChEBI
1,2-Dihexadecanoyl-rac-glycero-3-phospho-(1'-rac-glycerol)HMDB
1,2-Dipalmitoyl-rac-glycero-3-phosphoglycerolHMDB
1,2-Dihexadecanoyl-rac-glycero-3-phospho-(1'-glycerol)HMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphoglycerolHMDB
Bacteriocin 28b protein, bacteriaHMDB
Bacteriocin 28b structural protein, bacteriaHMDB
BSS Protein, bacteriaHMDB
PG(16:0/16:0)Lipid Annotator
1,2-Dipalmitoyl-glycero-3-phosphoglycerolHMDB
Chemical FormulaC38H75O10P
Average Molecular Weight722.982
Monoisotopic Molecular Weight722.509785613
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis(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)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C38H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39-40H,3-34H2,1-2H3,(H,43,44)/t35-,36+/m0/s1
InChI KeyBIABMEZBCHDPBV-MPQUPPDSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentPhosphatidylglycerols
Alternative Parents
Substituents
  • 1,2-diacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process