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Record Information
Version2.0
Creation Date2012-05-31 14:53:16 -0600
Update Date2015-06-03 17:20:23 -0600
Secondary Accession Numbers
  • ECMDB20610
Identification
Name:Sn-Glycerol-1-phosphate
DescriptionSn-glycerol-1-phosphate is a glycerol phosphate. It is a key substrate in phospholipid synthesis and phosphatidylglycerol sbiosynthesis. The sn-glycerol-3-phosphate acyltransferase (plsB) of Escherichia coli is a key regulatory enzyme that catalyzes the first committed step in phospholipid biosynthesis. (PMID 9393688) Fosmidomycin is a hydrophilic molecule and in many bacteria its uptake is an active process involving a cAMP dependent glycerol-3-phosphate transporter (GlpT). (PMID 18489786)
Structure
Thumb
Synonyms:
  • .alpha.-glycerophosphate
  • .alpha.-glycerophosphorate
  • .alpha.-glycerophosphoric acid
  • 1,2,3-Propanetriol, 1-(dihydrogen phosphate)
  • 1,2,3-Propanetriol, 1-(dihydrogen phosphoric acid)
  • 1-Glycerophosphate
  • 1-Glycerophosphorate
  • 1-Glycerophosphoric acid
  • 2,3-Dihydroxypropyl dihydrogen phosphate
  • 2,3-Dihydroxypropyl dihydrogen phosphoric acid
  • 2,3-Hydroxy-1-propyl dihydrogen phosphate
  • 2,3-Hydroxy-1-propyl dihydrogen phosphoric acid
  • 3-Glycerophosphate
  • 3-Glycerophosphoric acid
  • 3-Phosphoglycerol
  • a-Glycerophosphate
  • a-Glycerophosphorate
  • a-Glycerophosphoric acid
  • a-Phosphoglycerol
  • alpha-Glycerophosphate
  • Alpha-Glycerophosphorate
  • Alpha-Glycerophosphoric acid
  • Alpha-Phosphoglycerol
  • BBR
  • D-Glycerol 3-phosphate
  • D-Glycerol 3-phosphoric acid
  • Glycerol .alpha.-phosphate
  • Glycerol .alpha.-phosphoric acid
  • Glycerol 1-(dihydrogen phosphate)
  • Glycerol 1-(dihydrogen phosphoric acid)
  • Glycerol 1-phosphate
  • Glycerol 1-phosphoric acid
  • Glycerol 3-phosphate
  • Glycerol 3-phosphoric acid
  • Glycerol a-phosphate
  • Glycerol a-phosphoric acid
  • Glycerol alpha-phosphate
  • Glycerol alpha-phosphoric acid
  • Glycerol dihydrogen phosphate
  • Glycerol dihydrogen phosphoric acid
  • Glycerol α-phosphate
  • Glycerol α-phosphoric acid
  • Glycerol, 1-(dihydrogen phosphate)
  • Glycerol, 1-(dihydrogen phosphate) (8CI)
  • Glycerol, 1-(dihydrogen phosphoric acid)
  • Glycerol, 1-(dihydrogen phosphoric acid) (8ci)
  • GLYCEROL-3-PHOSPHATE
  • GLYCEROL-3-phosphoric acid
  • Glycerophosphate
  • Glycerophosphate i
  • Glycerophosphorate
  • Glycerophosphorate I
  • Glycerophosphoric acid
  • Glycerophosphoric acid I
  • L-Glycerol 1-phosphate
  • L-Glycerol 1-phosphoric acid
  • Sn-Glycerol 1-phosphate
  • sn-Glycerol 1-phosphoric acid
  • sn-Glycerol-1-phosphoric acid
  • SN-glyceryl phosphate
  • sn-Glyceryl phosphoric acid
  • [(2S)-2,3-dihydroxypropyl] dihydrogen phosphate
  • [(2S)-2,3-Dihydroxypropyl] dihydrogen phosphoric acid
  • α-Glycerophosphate
  • α-Glycerophosphorate
  • α-Glycerophosphoric acid
  • α-Phosphoglycerol
Chemical Formula:C3H9O6P
Weight:Average: 172.0737
Monoisotopic: 172.013674532
InChI Key:AWUCVROLDVIAJX-VKHMYHEASA-N
InChI:InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m0/s1
CAS number:5746-57-6
IUPAC Name:[(2S)-2,3-dihydroxypropoxy]phosphonic acid
Traditional IUPAC Name:glycerophosphate
SMILES:[H][C@](O)(CO)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct ParentGlycerophosphates
Alternative Parents
Substituents
  • Sn-glycerol-3-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility30.6 g/LALOGPS
logP-1.8ALOGPS
logP-2ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability13.45 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:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-5900000000-64043ee94d742cc4c8a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9400000000-a63f5ba86caa3b7c6ee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-cf0fb6dae7ed4a7915ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6900000000-da790cb57078431a7c1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-cd376066ff1f1f928911View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a6ed4a0320c8229c8621View 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:
  • Brown, A. C., Parish, T. (2008). "Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake." BMC Microbiol 8:78. Pubmed: 18489786
  • Heath, R. J., Goldfine, H., Rock, C. O. (1997). "A gene (plsD) from Clostridium butyricum that functionally substitutes for the sn-glycerol-3-phosphate acyltransferase gene (plsB) of Escherichia coli." J Bacteriol 179:7257-7263. Pubmed: 9393688
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16221
HMDB IDNot Available
Pubchem Compound ID754
Kegg IDC00623
ChemSpider ID388409
Wikipedia IDNot Available
BioCyc IDSN-GLYCEROL-1-PHOSPHATE
EcoCyc IDSN-GLYCEROL-1-PHOSPHATE
Ligand Expo1GP

Enzymes

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.