Record Information
Version2.0
Creation Date2012-05-31 14:39:25 -0600
Update Date2015-06-05 00:35:31 -0600
Secondary Accession Numbers
  • ECMDB20326
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
Thumb
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
Weight:Average: 96.0224
Monoisotopic: 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
DescriptionThis compound belongs to the class of chemical entities known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphonic acids and derivatives
Direct ParentOrganic phosphonic acids
Alternative Parents
Substituents
  • Organophosphonic acid
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:108.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:20 mg/mL [ROSENBLATT,DH et al. (1975)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility29.8 g/LALOGPS
logP-0.89ALOGPS
logP-1.2ChemAxon
logS-0.51ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.18 m³·mol⁻¹ChemAxon
Polarizability6.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
methylphosphonate degradation IPW002065 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Phosphonate and phosphinate metabolism ec00440
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-953ee27b6d4d39a23d75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-e9ec8666066269105129View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-9000000000-cfc27ecfe46b6bae99b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-548aafc3bd5ffd117ef4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-794c4f4a660b80340d80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-41de8276110f43fd3d44View 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
External Links:
ResourceLink
CHEBI ID45129
HMDB IDNot Available
Pubchem Compound ID13818
Kegg IDC20396
ChemSpider ID13220
Wikipedia IDNot Available
BioCyc IDCPD0-1068
EcoCyc IDCPD0-1068
Ligand ExpoPPM

Enzymes

General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnH and PhnI is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnL
Uniprot ID:
P16679
Molecular weight:
24705
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnH and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate. PhnI alone has nucleosidase activity, catalyzing the hydrolysis of ATP or GTP forming alpha-D-ribose 5-triphosphate and adenine or guanine, respectively.
Gene Name:
phnI
Uniprot ID:
P16687
Molecular weight:
38852
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
General function:
organic phosphonate catabolic process
Specific function:
Together with PhnG, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnH
Uniprot ID:
P16686
Molecular weight:
21027
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine
General function:
organic phosphonate transport
Specific function:
Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnG
Uniprot ID:
P16685
Molecular weight:
16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for phosphonates; probably responsible for the translocation of the substrate across the membrane
Gene Name:
phnE
Uniprot ID:
P16683
Molecular weight:
28383
General function:
organic phosphonate transport
Specific function:
Together with PhnH, PhnI and PhnL is required for the transfer of the ribose triphosphate moiety from ATP to methyl phosphonate.
Gene Name:
phnG
Uniprot ID:
P16685
Molecular weight:
16539
Reactions
ATP + methylphosphonate = alpha-D-ribose 1-methylphosphonate 5-triphosphate + adenine