Show more...Show more...
Record Information
Version1.0
Creation Date2016-09-30 23:00:42 UTC
Update Date2020-05-05 18:40:22 UTC
MCDB ID BMDB0002520
Secondary Accession Numbers
  • BMDB02520
Metabolite Identification
Common NameBeta-Glycerophosphoric acid
DescriptionGlycerol 2-phosphate, also known as beta-glycerophosphate, belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group. Glycerol 2-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerol 2-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
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
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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected but not QuantifiedNot Applicable
  • Characterization ...
details
HMDB IDHMDB0002520
DrugBank IDDB01779
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023021
KNApSAcK IDC00007407
Chemspider ID2431
KEGG Compound IDC02979
BioCyc IDCPD-536
BiGG IDNot Available
Wikipedia LinkGlycerol_2-phosphate
METLIN ID6708
PubChem Compound2526
PDB IDNot Available
ChEBI ID17270
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals (2009). Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics.