2.0 2012-05-31 14:39:25 -0600 2015-06-05 00:35:31 -0600 ECMDB20326 M2MDB001160 Methylphosphonate 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. 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 CH5O3P 96.0224 95.997630538 methylphosphonic acid methylphosphonic acid 993-13-5 CP(O)(O)=O InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4) YACKEPLHDIMKIO-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.89 ALOGPS logs -0.51 ALOGPS solubility 2.98e+01 g/l ALOGPS melting_point 108.5 oC logp -1.2 ChemAxon pka_strongest_acidic 1.87 ChemAxon iupac methylphosphonic acid ChemAxon average_mass 96.0224 ChemAxon mono_mass 95.997630538 ChemAxon smiles CP(O)(O)=O ChemAxon formula CH5O3P ChemAxon inchi InChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4) ChemAxon inchikey YACKEPLHDIMKIO-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 17.18 ChemAxon polarizability 6.91 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Phosphonate and phosphinate metabolism ec00440 methylphosphonate degradation I The pathway of methylphosphonate degradation starts with methylphosphonate being degrade by an ATP driven methylphosphonate degradation complex resulting in a alpha-D-ribose-1-methylphosphonate-5-triphosphate. This compound in turn is degraded by a water driven RPnTP hydrolase resulting in the release of a hydrogen ion, a pyrophosphate and a alpha-Dribose-1-methylphosphonate 5-phosphate. The latter compound is then involved with a carbon-phosphorous lyase resulting in the release of a methane and a 5-phospho-alpha-D-ribose 1,2-cyclic phosphate. This compound in turn gets degraded by a water driven 5-phospho-alpha-D-ribosyl 1,2-cyclic phosphate phosphodiesterase resulting in the release of a hydrogen ion and a alpha-D-ribose 1,5-biphosphate. PW002065 Metabolic methylphosphonate degradation PWY0-1533 Specdb::CMs 137860 Specdb::CMs 145594 Specdb::NmrOneD 76592 Specdb::NmrOneD 76593 Specdb::NmrOneD 76594 Specdb::NmrOneD 76595 Specdb::NmrOneD 76596 Specdb::NmrOneD 76597 Specdb::NmrOneD 76598 Specdb::NmrOneD 76599 Specdb::NmrOneD 76600 Specdb::NmrOneD 76601 Specdb::NmrOneD 76602 Specdb::NmrOneD 76603 Specdb::NmrOneD 76604 Specdb::NmrOneD 76605 Specdb::NmrOneD 76606 Specdb::NmrOneD 76607 Specdb::NmrOneD 76608 Specdb::NmrOneD 76609 Specdb::NmrOneD 76610 Specdb::NmrOneD 76611 Specdb::MsMs 24593 Specdb::MsMs 24594 Specdb::MsMs 24595 Specdb::MsMs 31151 Specdb::MsMs 31152 Specdb::MsMs 31153 Specdb::MsMs 2273241 Specdb::MsMs 2273242 Specdb::MsMs 2273243 Specdb::MsMs 3069150 Specdb::MsMs 3069151 Specdb::MsMs 3069152 13818 13220 C20396 45129 CPD0-1068 PPM 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. 21097882 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. 22080510 Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnL P16679 PHNL_ECOLI phnL http://ecmdb.ca/proteins/P16679.xml Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnI P16687 PHNI_ECOLI phnI http://ecmdb.ca/proteins/P16687.xml Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnH P16686 PHNH_ECOLI phnH http://ecmdb.ca/proteins/P16686.xml Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG P16685 PHNG_ECOLI phnG http://ecmdb.ca/proteins/P16685.xml Putative phosphonates transport system permease protein phnE P16683 PHNE_ECOLI phnE http://ecmdb.ca/proteins/P16683.xml Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG P16685 PHNG_ECOLI phnG http://ecmdb.ca/proteins/P16685.xml Methylphosphonate + Adenosine triphosphate > α-D-ribose-1-methylphosphonate-5-triphosphate + Adenine RXN0-6732 Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine R10185 Methylphosphonate + Adenosine triphosphate > Adenine + alpha-D-Ribose 1-methylphosphonate 5-triphosphate PW_R006035 Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine