Record Information
Version2.0
Creation Date2012-05-31 14:05:59 -0600
Update Date2015-06-03 15:54:46 -0600
Secondary Accession Numbers
  • ECMDB04130
Identification
Name:Phosphoglycolic acid
Description2-Phosphoglycolic acid is a substrate for 2-phosphoglycolate phosphatase from Escherichia coli, which is encoded by the gph gene. It is converted to glycolic acid which is involved in general two-carbon metabolism. This housekeeping enzyme is involved in the dissimilation of the intracellular 2-phosphoglycolate formed in the DNA repair of 3'-phosphoglycolate ends.
Structure
Thumb
Synonyms:
  • (phosphonooxy)-acetate
  • (phosphonooxy)-acetic acid
  • (Phosphonooxy)acetate
  • (Phosphonooxy)acetic acid
  • 2-P-Glycolate
  • 2-P-Glycolic acid
  • 2-Phosphoglycolate
  • 2-Phosphoglycolic acid
  • Glycolate di-H phosphate
  • Glycolate dihydrogen phosphate
  • Glycolate phosphate
  • Glycolic acid di-H phosphate
  • Glycolic acid di-H phosphoric acid
  • Glycolic acid dihydrogen phosphate
  • Glycolic acid dihydrogen phosphoric acid
  • Glycolic acid phosphate
  • Glycolic acid phosphoric acid
  • Glycophosphate
  • Glycophosphorate
  • Glycophosphoric acid
  • Phosphoglycolate
  • Phosphoglycolic acid
Chemical Formula:C2H5O6P
Weight:Average: 156.0313
Monoisotopic: 155.982374404
InChI Key:ASCFNMCAHFUBCO-UHFFFAOYSA-N
InChI:InChI=1S/C2H5O6P/c3-2(4)1-8-9(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
CAS number:13147-57-4
IUPAC Name:2-(phosphonooxy)acetic acid
Traditional IUPAC Name:phosphoglycolate
SMILES:OC(=O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility18.4 g/LALOGPS
logP-2.3ALOGPS
logP-1.2ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.14ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.22 m³·mol⁻¹ChemAxon
Polarizability10.67 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:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0bwa-1954000000-58b32347feea7c57657dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bwa-1954000000-58b32347feea7c57657dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bwa-1954000000-58b32347feea7c57657dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0532-0943000000-b46adc0d53ca876bee97View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-510bbb9f20d9bfcbb49dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01vt-9410000000-2ec3fa590a794453d406View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-72a0567ec4387e0d910fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-a18204a3ef12341ad757View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9700000000-b6a20a78eceb3021333fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-3900000000-e1fa686e95d11683b169View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-e7d5d6506767e5e94a14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-36a54b95f105df968214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9100000000-16d619e555184d5bedb5View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-8900000000-fb381315634c74b7a800View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9400000000-09d97cff7876c29ad758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-e96b44c7cf4870c8a3cbView 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
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Synthesis Reference:Courtois, Jean. Action of periodic acid on hexosediphosphoric acid. Compt. rend. (1941), 212 1172-4. CAN 38:22678 AN 1944:22678
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17150
HMDB IDHMDB00816
Pubchem Compound ID529
Kegg IDC00988
ChemSpider ID514
Wikipedia IDNot Available
BioCyc IDCPD-67
EcoCyc IDCPD-67
Ligand ExpoPGA

Enzymes

General function:
Involved in catalytic activity
Specific function:
Specifically catalyzes the dephosphorylation of 2- phosphoglycolate. Is involved in the dissimilation of the intracellular 2-phosphoglycolate formed during the DNA repair of 3'-phosphoglycolate ends, a major class of DNA lesions induced by oxidative stress
Gene Name:
gph
Uniprot ID:
P32662
Molecular weight:
27389
Reactions
2-phosphoglycolate + H(2)O = glycolate + phosphate.