P. aeruginosa Metabolome Database: Propanoyl phosphate (PAMDB001030)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001030

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

🔍MOL SDF PDB SMILES InChI View Structure

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 Description

This 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 Class

Organophosphorus compounds

Class

Organic phosphoric acids and derivatives

Sub Class

Organic 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

acyl monophosphate (CHEBI:8478 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

2.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	1.45 mg/mL at 25 oC [HUYSKENS,P et al. (1975)]	PhysProp
LogP:	-0.781	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	20.1 mg/mL	ALOGPS
logP	-0.32	ALOGPS
logP	-0.18	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.43 m³·mol^-1	ChemAxon
Polarizability	11.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Adenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphate
Propionyl-CoA + Phosphate > Propanoyl phosphate + Coenzyme A
Propionyl-CoA + Phosphate + Propionyl-CoA > Coenzyme A + propanoyl phosphate + Propanoyl phosphate
Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acid

Pathways:

C5-Branched dibasic acid metabolism pae00660
Propanoate metabolism pae00640

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-9600000000-ae6f398b30d307d44385	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9100000000-02c4298d3d22d7a77700	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9000000000-1250b86892c1e543c420	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9300000000-c22e101279f54e92d9c3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-ca5b2a41e681506687c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-8a0afbbb52e6c2bc4a19	View 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

Links

External Links:

Resource	Link
CHEBI ID	16269
HMDB ID	Not Available
Pubchem Compound ID	1034
Kegg ID	C02876
ChemSpider ID	1007
Wikipedia ID	Not Available
BioCyc ID	PROPIONYL-P
EcoCyc ID	PROPIONYL-P

Propanoyl phosphate (PAMDB001030)

Structure for Propanoyl phosphate (PAMDB001030)