Record Information
Version2.0
Creation Date2012-05-31 14:31:58 -0600
Update Date2015-09-17 15:42:09 -0600
Secondary Accession Numbers
  • ECMDB20184
Identification
Name:Propanoyl phosphate
DescriptionPropanoyl 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
Weight:Average: 152.043
Monoisotopic: 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
Description belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentAcyl monophosphates
Alternative Parents
Substituents
  • Acyl monophosphate
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.43 m³·mol⁻¹ChemAxon
Polarizability11.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
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

Enzymes

General function:
Involved in kinase activity
Specific function:
Involved in the activation of acetate to acetyl CoA and the secretion of acetate. During anaerobic growth of the organism, this enzyme is also involved in the synthesis of most of the ATP formed catabolically
Gene Name:
ackA
Uniprot ID:
P0A6A3
Molecular weight:
43290
Reactions
ATP + acetate = ADP + acetyl phosphate.
ATP + propanoate = ADP + propanoyl phosphate.
General function:
Involved in phosphate acetyltransferase activity
Specific function:
Acetyl-CoA + phosphate = CoA + acetyl phosphate
Gene Name:
pta
Uniprot ID:
P0A9M8
Molecular weight:
77171
Reactions
Acetyl-CoA + phosphate = CoA + acetyl phosphate.
General function:
Involved in kinase activity
Specific function:
ATP + propanoate = ADP + propanoyl phosphate
Gene Name:
tdcD
Uniprot ID:
P11868
Molecular weight:
43384
Reactions
ATP + propanoate = ADP + propanoyl phosphate.
ATP + acetate = ADP + acetyl phosphate.