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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:55 UTC
Update Date2018-05-20 09:56:41 UTC
HMDB IDHMDB0002520
Secondary Accession Numbers
  • HMDB02520
Metabolite Identification
Common NameBeta-Glycerophosphoric acid
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
Synonyms
ValueSource
1,2,3-Propanetriol, 2-(dihydrogen phosphate)ChEBI
1,3-Hydroxy-2-propyl dihydrogen phosphateChEBI
2-GlycerophosphateChEBI
2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen phosphATEChEBI
beta-GlycerophosphateChEBI
1,2,3-Propanetriol, 2-(dihydrogen phosphoric acid)Generator
b-GlycerophosphateGenerator
b-Glycerophosphoric acidGenerator
β-glycerophosphateGenerator
β-glycerophosphoric acidGenerator
1,3-Hydroxy-2-propyl dihydrogen phosphoric acidGenerator
2-Glycerophosphoric acidGenerator
2-HYDROXY-1-(hydroxymethyl)ethyl dihydrogen phosphoric acidGenerator
beta-GlycerophosphorateHMDB
Glycerol-2-phosphateHMDB
beta-Glycerol phosphateMeSH
beta-Glycerophosphoric acid, calcium saltMeSH
beta-Glycerophosphoric acid, disodium saltMeSH
beta-Glycerophosphoric acid, sodium saltMeSH
beta-Glycerophosphoric acid, calcium salt (1:1)MeSH
beta-Glycerophosphoric acid, iron saltMeSH
beta-Glycerophosphoric acid, iron(3+) salt(3:2)MeSH
Chemical FormulaC3H9O6P
Average Molecular Weight172.0737
Monoisotopic Molecular Weight172.013674532
IUPAC Name[(1,3-dihydroxypropan-2-yl)oxy]phosphonic acid
Traditional Nameβ-glycerophosphorate
CAS Registry Number17181-54-3
SMILES
OCC(CO)OP(O)(O)=O
InChI Identifier
InChI=1S/C3H9O6P/c4-1-3(2-5)9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)
InChI KeyDHCLVCXQIBBOPH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycerophosphates. These 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
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9200000000-494acb690fc0f406808aView 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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB01779
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023021
KNApSAcK IDC00007407
Chemspider ID2431
KEGG Compound IDC02979
BioCyc IDCPD-536
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6708
PubChem Compound2526
PDB IDG2H
ChEBI ID17270
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]