Record Information
Version2.0
Creation Date2012-08-15 08:51:33 -0600
Update Date2015-06-03 17:22:01 -0600
Secondary Accession Numbers
  • ECMDB21656
Identification
Name:Phosphatidylglycerophosphate
DescriptionPhosphatidylglycerophosphate belongs to the class of Phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
Structure
Thumb
Synonyms:
  • 1,2-Diacyl-sn-glycero-3-phospho-sn-glycerol 3'-phosphate
  • 1,2-Diacyl-sn-glycero-3-phospho-sn-glycerol 3'-phosphoric acid
  • 3(3-Phosphatidyl-)L-glycerol 1-phosphate
  • 3(3-Phosphatidyl-)L-glycerol 1-phosphoric acid
  • 3(3-Sn-Phosphatidyl)-sn-glycerol 1-phosphate
  • 3(3-sn-Phosphatidyl)-sn-glycerol 1-phosphoric acid
  • Phosphatidylglycerol phosphates
  • Phosphatidylglycerophosphate
  • Phosphatidylglycerophosphoric acid
Chemical Formula:C8H16O13P2
Weight:Average: 382.1524
Monoisotopic: 382.006613622
InChI Key:ZSPJCYNIVYENCI-JGVFFNPUSA-N
InChI:InChI=1S/C8H16O13P2/c9-5-17-3-8(18-6-10)4-21-23(15,16)20-2-7(11)1-19-22(12,13)14/h5-8,11H,1-4H2,(H,15,16)(H2,12,13,14)/t7-,8+/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-3-({[(2R)-2,3-bis(formyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:(2S)-3-{[(2R)-2,3-bis(formyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid
SMILES:[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC=O)OC=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerophosphates
Direct ParentPhosphatidylglycerophosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoglycerophosphate
  • Sn-glycerol-3-phosphate
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.66 g/LALOGPS
logP-1.1ALOGPS
logP-2.2ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.35 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity68.32 m³·mol⁻¹ChemAxon
Polarizability29.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-2449000000-4432684415598adfd898View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053j-6962000000-9a805aadc83776f292dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9710000000-d71253aac77bc3c982afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-9148000000-e1b34167e5f0ead87adeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-9d16e501b9bf5a96a54fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f6224db456271dac0375View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17264
HMDB IDNot Available
Pubchem Compound ID46873832
Kegg IDC03892
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
This protein catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
pgsA
Uniprot ID:
P0ABF8
Molecular weight:
20700
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
General function:
Involved in phosphatidylglycerophosphatase activity
Specific function:
One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:
pgpA
Uniprot ID:
P18200
Molecular weight:
19418
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
General function:
phospholipid catabolic process
Specific function:
Lipid phosphatase which dephosphorylates phosphatidylglycerophosphate (PGP) to phosphatidylglycerol (PG).
Gene Name:
pgpC
Uniprot ID:
P0AD42
Molecular weight:
24439
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate