P. aeruginosa Metabolome Database: Methylphosphonate (PAMDB001160)

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

PAMDB001160

Identification

Name:

Methylphosphonate

Description:

Methylphosphonate is a member of the chemical class known as Organic Phosphonic Acids and Derivatives. These are organic compounds containing phosphonic acid or a derivative thereof. . Phosphonates (Pn) are a large class of organophosphorus molecules that have direct carbon-phosphorus (C-P) bonds in place of the carbon-oxygen-phosphorus ester bond. In bacteria two pathways exist for Pn breakdown for use as a P source: the phosphonatase and C-P lyase pathways. These pathways differ both in regard to their substrate specificity and their cleavage mechanism. The phosphonatase pathway acts on the natural Pn alpha-aminoethylphosphonate (AEPn). In a two-step process it leads to cleavage of the C-P bond by a hydrolysis reaction requiring an adjacent carbonyl group. In contrast the C-P lyase pathway has a broad substrate specificity. It leads to cleavage of substituted Pn (such as AEPn) as well as unsubstituted Pn by a mechanism involving redox or radical chemistry. Due to its broad substrate specificity, the C-P lyase pathway is generally thought to be responsible for the breakdown of Pn herbicides (such as glyphosate) by bacteria.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

GB
M-Carboxyphenyl phenylacetamidomethylphosphonate
M-Carboxyphenyl phenylacetamidomethylphosphonic acid
MePn
Methanephosphonate
Methanephosphonic acid
Methyl phosphonate
Methyl phosphonic acid
Methyl-Phosphonate
Methyl-Phosphonic acid
Methylphosphonic acid
Phosphonomethyl group
PPM
VXA

Chemical Formula:

CH₅O₃P

Average Molecular Weight:

96.0224

Monoisotopic Molecular Weight:

95.997630538

InChI Key:

YACKEPLHDIMKIO-UHFFFAOYSA-N

InChI:

InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)

CAS number:

993-13-5

IUPAC Name:

methylphosphonic acid

Traditional IUPAC Name:

methylphosphonic acid

SMILES:

CP(O)(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organic phosphonic acids and derivatives

Sub Class

Organic phosphonic acids

Direct Parent

Organic phosphonic acids

Alternative Parents

Hydrocarbon derivatives

Substituents

Organophosphonic acid
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:45129 )
phosphonic acids (CHEBI:45129 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

108.5 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	20 mg/mL [ROSENBLATT,DH et al. (1975)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	29.8 mg/mL	ALOGPS
logP	-0.89	ALOGPS
logP	-1.2	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	17.18 m³·mol^-1	ChemAxon
Polarizability	6.91 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:

Methylphosphonate + Adenosine triphosphate > α-D-ribose-1-methylphosphonate-5-triphosphate + Adenine
Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine

Pathways:

Phosphonate and phosphinate metabolism pae00440

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-953ee27b6d4d39a23d75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-e9ec8666066269105129	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ls-9000000000-cfc27ecfe46b6bae99b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-548aafc3bd5ffd117ef4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-794c4f4a660b80340d80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-41de8276110f43fd3d44	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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	45129
HMDB ID	Not Available
Pubchem Compound ID	13818
Kegg ID	C20396
ChemSpider ID	13220
Wikipedia ID	Methylphosphonic acid
BioCyc ID	CPD0-1068
EcoCyc ID	CPD0-1068
Ligand Expo	PPM

Methylphosphonate (PAMDB001160)

Structure for Methylphosphonate (PAMDB001160)