Glycerol 2-phosphate (ECMDB21222) (M2MDB001630)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (6)Transporters (8)XML
Proteins (10)
Record Information
Version2.0
Creation Date2012-07-30 14:54:59 -0600
Update Date2015-06-03 17:20:55 -0600
Secondary Accession Numbers
  • ECMDB21222
Identification
Name:Glycerol 2-phosphate
DescriptionGlycerol-2-phosphate is a component of glycerolipid metabolism. It is formed in minor quanitites, as the alpha glycerophosphorate is preferentially formed in this manner. Also used as a biological buffer (Sigma-Aldrich).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • β-glycerol-phosphate
  • β-glycerol-phosphoric acid
  • 1,2,3-Propanetriol, 2-(dihydrogen phosphate)
  • 1,2,3-Propanetriol, 2-(dihydrogen phosphoric acid)
  • 1,3-Hydroxy-2-propyl dihydrogen phosphate
  • 1,3-Hydroxy-2-propyl dihydrogen phosphoric acid
  • 2-Glycerophosphate
  • 2-Glycerophosphoric acid
  • 2-HYDROXY-1-(HYDROXYMETHYL)ETHYL DIHYDROGEN PHOSPHATE
  • 2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen phosphoric acid
  • B-Glycerol-phosphate
  • b-Glycerol-phosphoric acid
  • b-Glycerophosphate
  • b-Glycerophosphorate
  • b-Glycerophosphoric acid
  • Beta-Glycerol-phosphate
  • beta-Glycerol-phosphoric acid
  • beta-Glycerophosphate
  • Beta-Glycerophosphorate
  • Beta-Glycerophosphoric acid
  • Glycerol 2-(dihydrogen phosphate)
  • Glycerol 2-(dihydrogen phosphoric acid)
  • Glycerol 2-phosphate
  • Glycerol 2-phosphoric acid
  • Glycerol-2-phosphate
  • Glycerol-2-phosphoric acid
  • β-Glycerol-phosphate
  • β-Glycerol-phosphoric acid
  • β-Glycerophosphate
  • β-Glycerophosphorate
  • β-Glycerophosphoric acid
Chemical Formula:C3H9O6P
Weight:Average: 172.0737
Monoisotopic: 172.013674532
InChI Key:DHCLVCXQIBBOPH-UHFFFAOYSA-N
InChI:InChI=1S/C3H9O6P/c4-1-3(2-5)9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)
CAS number:17181-54-3
IUPAC Name:[(1,3-dihydroxypropan-2-yl)oxy]phosphonic acid
Traditional IUPAC Name:β-glycerophosphorate
SMILES:OCC(CO)OP(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-2-phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility30.7 g/LALOGPS
logP-1.8ALOGPS
logP-2ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.13ChemAxon
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
Polarizability13.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + Glycerol 2-phosphate > ADP + Glycerol 2-phosphate + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + Glycerol 2-phosphate > ADP + Glycerol 2-phosphate + Hydrogen ion + Phosphate
Glycerol 2-phosphate + Water > Glycerol + Phosphate
Glycerol 2-phosphate + Water + Adenosine triphosphate > Glycerol 2-phosphate + ADP + Hydrogen ion + Phosphate
Glycerol 2-phosphate + Water + Adenosine triphosphate > Glycerol 2-phosphate + ADP + Hydrogen ion + Phosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0gvp-1792000000-c48ad0477aac597f9e48View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gwe-0981000000-ffc7c737ad151bab34f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gvp-1792000000-c48ad0477aac597f9e48View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gvn-0971000000-02ef7a6a93f26d18e2e9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-f3b980cd6beaf038fb5cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0gi0-5930000000-043db2c19de48a1a22adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9200000000-494acb690fc0f406808aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-4944c6b0c8f6d1d30e93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-178dacbbcce6f01b32e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-0d15a9e9ccd8f0340debView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-0ea1a0eba5ca2510e52aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-9b83578d72246c176ae2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9100000000-44e85363da094bc39958View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-e6b7983e77544a2cf2deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-5d410b074c244fb15b59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-814132cc0e794598b88aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-415393e808bbb4c6847cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-9200000000-a6921adb8e95e92d8015View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1391ae42d78e238c7378View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9100000000-b7bb3126c390b73c7eb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-9200000000-a2e1932c879b8360e2a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-eaf5bd1508ba8779087fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ba-9100000000-767830ab29256b7438a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-ea2a52269bc5d4ed4c52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-6692d72b52d1a7b9adeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-5900000000-6fc5f19f68de2c6954f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-ff45373c539658924e8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3c7e37432300e646a900View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9100000000-e8c9470a4d96519f535aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView 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:
  • Chamberlin BA, Sweeley CC: Metabolic profiles of urinary organic acids recovered from absorbent filter paper. Clin Chem. 1987 Apr;33(4):572-6. Pubmed: 3829393
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17270
HMDB IDHMDB02520
Pubchem Compound ID2526
Kegg IDC02979
ChemSpider ID2431
Wikipedia IDGlycerol_2-phosphate
BioCyc IDCPD-536
EcoCyc IDCPD-536
Ligand ExpoG2H

Enzymes

Protein Details
1. Inositol-1-monophosphatase
General function:
Involved in phosphatidylinositol phosphorylation
Specific function:
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate
Gene Name:
suhB
Uniprot ID:
P0ADG4
Molecular weight:
29172
Reactions
Myo-inositol phosphate + H(2)O = myo-inositol + phosphate.
Protein Details
2. Class B acid phosphatase
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
Protein Details
3. sn-glycerol-3-phosphate import ATP-binding protein UgpC
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
Protein Details
4. sn-glycerol-3-phosphate transport system permease protein ugpA
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
Protein Details
5. sn-glycerol-3-phosphate transport system permease protein ugpE
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
Protein Details
6. sn-glycerol-3-phosphate-binding periplasmic protein ugpB
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448

Transporters

Protein Details
1. sn-glycerol-3-phosphate import ATP-binding protein UgpC
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:
ugpC
Uniprot ID:
P10907
Molecular weight:
39524
Reactions
ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).
Protein Details
2. sn-glycerol-3-phosphate transport system permease protein ugpA
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpA
Uniprot ID:
P10905
Molecular weight:
33264
Protein Details
3. sn-glycerol-3-phosphate transport system permease protein ugpE
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:
ugpE
Uniprot ID:
P10906
Molecular weight:
31499
Protein Details
4. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
5. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
6. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
7. sn-glycerol-3-phosphate-binding periplasmic protein ugpB
General function:
Involved in transporter activity
Specific function:
sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:
ugpB
Uniprot ID:
P0AG80
Molecular weight:
48448
Protein Details
8. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368