Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001030
Identification
Name: Propanoyl phosphate
Description:Propanoyl phosphate is an alkylphosphate. It is generated during the course of threonine degradation via propanoyl-CoA. The first reaction in the anaerobic threonine dehydratase pathway is catalyzed by catabolic threonine dehydratase which degrades threonine to 2-oxobutanoate (alpha-ketobutyrate) and ammonia. The 2-oxobutanoate then undergoes lyase cleavage with the addition of coenzyme A to form propanoyl-CoA and formate. Once propanoyl-CoA is formed, it is processed via propionyl-phosphate to propionate in a reaction sequence that produces ATP. Acetate kinase AckA can also utilize propionate as a substrate in the final reaction. The enzymes in this pathway are also able to process L-serine, with pyruvate as the final product [EcoCyc].
Structure
Thumb
Synonyms:
  • Propanoyl phosphoric acid
  • Propanoyl-P
  • Propionyl phosphate
  • Propionyl phosphoric acid
  • Propionyl-P
  • Propionyl-phosphate
  • Propionyl-phosphoric acid
Chemical Formula: C3H5O5P
Average Molecular Weight: 152.043
Monoisotopic Molecular Weight: 151.988557419
InChI Key: FMNMEQSRDWIBFO-UHFFFAOYSA-L
InChI:InChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2
CAS number: 121-69-7
IUPAC Name:(propanoyloxy)phosphonic acid
Traditional IUPAC Name: propionyl phosphate
SMILES:CCC(=O)OP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as organic phosphoric acids. These are organic compounds containing phosphoric acid, with the general structure OP(O)(=O)O.
Kingdom Organic compounds
Super ClassOrganophosphorus compounds
Class Organic phosphoric acids and derivatives
Sub ClassOrganic phosphoric acids
Direct Parent Organic phosphoric acids
Alternative Parents
Substituents
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 2.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1.45 mg/mL at 25 oC [HUYSKENS,P et al. (1975)]PhysProp
LogP:-0.781PhysProp
Predicted Properties
PropertyValueSource
Water Solubility20.1 mg/mLALOGPS
logP-0.32ALOGPS
logP-0.18ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.43 m3·mol-1ChemAxon
Polarizability11.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-ae6f398b30d307d44385View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-02c4298d3d22d7a77700View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-1250b86892c1e543c420View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9300000000-c22e101279f54e92d9c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-ca5b2a41e681506687c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8a0afbbb52e6c2bc4a19View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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 ID16269
HMDB IDNot Available
Pubchem Compound ID1034
Kegg IDC02876
ChemSpider ID1007
Wikipedia IDNot Available
BioCyc IDPROPIONYL-P
EcoCyc IDPROPIONYL-P