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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-09-18 15:59:51 UTC
HMDB IDHMDB0000816
Secondary Accession Numbers
  • HMDB0060148
  • HMDB00816
  • HMDB60148
Metabolite Identification
Common NamePhosphoglycolic acid
DescriptionPhosphoglycolic acid, also known as phosphoglycolate or glycolate-2-p, 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. Phosphoglycolic acid is a moderately acidic compound (based on its pKa). Phosphoglycolic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Phosphoglycolic acid has been detected, but not quantified in, several different foods, such as pomegranates, atlantic herrings, peachs, common verbena, and redcurrants. This could make phosphoglycolic acid a potential biomarker for the consumption of these foods. The O-phospho derivative of glycolic acid.
Structure
Data?1600444791
Synonyms
ValueSource
2-PhosphoglycolateChEBI
2-Phosphoglycolic acidGenerator
PhosphoglycolateGenerator
2-PhosphoglicolateMeSH
Glycolate-2-pMeSH
(Phosphonooxy)-acetateHMDB
(Phosphonooxy)-acetic acidHMDB
(Phosphonooxy)acetateHMDB
(Phosphonooxy)acetic acidHMDB
2-PhosphonatoglycolateHMDB
Glycolic acid di-H phosphateHMDB
Glycolic acid dihydrogen phosphateHMDB
Glycolic acid phosphateHMDB
GlycophosphorateHMDB
Glycophosphoric acidHMDB
Chemical FormulaC2H5O6P
Average Molecular Weight156.0313
Monoisotopic Molecular Weight155.982374404
IUPAC Name2-(phosphonooxy)acetic acid
Traditional Namephosphoglycolate
CAS Registry Number13147-57-4
SMILES
OC(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O6P/c3-2(4)1-8-9(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
InChI KeyASCFNMCAHFUBCO-UHFFFAOYSA-N
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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.24131661259
DarkChem[M-H]-125.30531661259
AllCCS[M+H]+134.86332859911
AllCCS[M-H]-125.8632859911
DeepCCS[M+H]+121.75730932474
DeepCCS[M-H]-118.9530932474
DeepCCS[M-2H]-155.67130932474
DeepCCS[M+Na]+130.39130932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.932859911
AllCCS[M+NH4]+138.632859911
AllCCS[M+Na]+139.732859911
AllCCS[M-H]-125.932859911
AllCCS[M+Na-2H]-128.632859911
AllCCS[M+HCOO]-131.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phosphoglycolic acidOC(=O)COP(O)(O)=O2479.5Standard polar33892256
Phosphoglycolic acidOC(=O)COP(O)(O)=O1308.1Standard non polar33892256
Phosphoglycolic acidOC(=O)COP(O)(O)=O1512.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phosphoglycolic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O)O1485.1Semi standard non polar33892256
Phosphoglycolic acid,1TMS,isomer #2C[Si](C)(C)OP(=O)(O)OCC(=O)O1511.0Semi standard non polar33892256
Phosphoglycolic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C1538.7Semi standard non polar33892256
Phosphoglycolic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C1512.6Standard non polar33892256
Phosphoglycolic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C1974.8Standard polar33892256
Phosphoglycolic acid,2TMS,isomer #2C[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C1578.3Semi standard non polar33892256
Phosphoglycolic acid,2TMS,isomer #2C[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C1553.7Standard non polar33892256
Phosphoglycolic acid,2TMS,isomer #2C[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C1754.9Standard polar33892256
Phosphoglycolic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1590.8Semi standard non polar33892256
Phosphoglycolic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1580.4Standard non polar33892256
Phosphoglycolic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C1683.0Standard polar33892256
Phosphoglycolic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O)O1713.2Semi standard non polar33892256
Phosphoglycolic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(O)OCC(=O)O1760.8Semi standard non polar33892256
Phosphoglycolic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C1949.3Semi standard non polar33892256
Phosphoglycolic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C1981.3Standard non polar33892256
Phosphoglycolic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2204.1Standard polar33892256
Phosphoglycolic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C(C)(C)C2003.1Semi standard non polar33892256
Phosphoglycolic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C(C)(C)C1967.9Standard non polar33892256
Phosphoglycolic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OP(=O)(OCC(=O)O)O[Si](C)(C)C(C)(C)C2007.6Standard polar33892256
Phosphoglycolic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2182.7Semi standard non polar33892256
Phosphoglycolic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2189.7Standard non polar33892256
Phosphoglycolic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2055.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phosphoglycolic acid GC-MS (3 TMS)splash10-0bwa-1954000000-58b32347feea7c57657d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phosphoglycolic acid GC-MS (Non-derivatized)splash10-0bwa-1954000000-58b32347feea7c57657d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phosphoglycolic acid GC-MS (Non-derivatized)splash10-0bwa-1954000000-58b32347feea7c57657d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phosphoglycolic acid GC-EI-TOF (Non-derivatized)splash10-0532-0943000000-b46adc0d53ca876bee972017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-510bbb9f20d9bfcbb49d2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01vt-9410000000-2ec3fa590a794453d4062017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoglycolic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 10V, Positive-QTOFsplash10-0a4i-0900000000-72a0567ec4387e0d910f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 20V, Positive-QTOFsplash10-052r-0900000000-a18204a3ef12341ad7572015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 40V, Positive-QTOFsplash10-052r-9700000000-b6a20a78eceb3021333f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 10V, Negative-QTOFsplash10-0ufr-3900000000-e1fa686e95d11683b1692015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 20V, Negative-QTOFsplash10-004i-9200000000-e7d5d6506767e5e94a142015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 40V, Negative-QTOFsplash10-004i-9000000000-36a54b95f105df9682142015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 10V, Negative-QTOFsplash10-004i-9100000000-16d619e555184d5bedb52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 20V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 10V, Positive-QTOFsplash10-0a4r-8900000000-fb381315634c74b7a8002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 20V, Positive-QTOFsplash10-0a4i-9400000000-09d97cff7876c29ad7582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoglycolic acid 40V, Positive-QTOFsplash10-001i-9000000000-e96b44c7cf4870c8a3cb2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02726
Phenol Explorer Compound IDNot Available
FooDB IDFDB030360
KNApSAcK IDC00007561
Chemspider ID514
KEGG Compound IDC00988
BioCyc IDCPD-67
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound529
PDB IDNot Available
ChEBI ID17150
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceCourtois, 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
General References
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Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
TPI1
Uniprot ID:
P60174
Molecular weight:
26669.33
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PGP
Uniprot ID:
A6NDG6
Molecular weight:
34005.69
Reactions
Phosphoglycolic acid + Water → Glycolic acid + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
D-glyceraldehyde 3-phosphate = glycerone phosphate
Gene Name:
Not Available
Uniprot ID:
Q2QD09
Molecular weight:
26942.6