2.02012-05-31 14:39:25 -06002015-06-05 00:35:31 -0600ECMDB20326M2MDB001160MethylphosphonateMethylphosphonate 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. GBM-Carboxyphenyl phenylacetamidomethylphosphonateM-Carboxyphenyl phenylacetamidomethylphosphonic acidMePnMethanephosphonateMethanephosphonic acidMethyl phosphonateMethyl phosphonic acidMethyl-PhosphonateMethyl-Phosphonic acidMethylphosphonic acidPhosphonomethyl groupPPMVXACH5O3P96.022495.997630538methylphosphonic acidmethylphosphonic acid993-13-5CP(O)(O)=OInChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)YACKEPLHDIMKIO-UHFFFAOYSA-NSolidCytoplasmPeriplasmlogp-0.89logs-0.51solubility2.98e+01 g/lmelting_point108.5 oClogp-1.2pka_strongest_acidic1.87iupacmethylphosphonic acidaverage_mass96.0224mono_mass95.997630538smilesCP(O)(O)=OformulaCH5O3PinchiInChI=1S/CH5O3P/c1-5(2,3)4/h1H3,(H2,2,3,4)inchikeyYACKEPLHDIMKIO-UHFFFAOYSA-Npolar_surface_area57.53refractivity17.18polarizability6.91rotatable_bond_count0acceptor_count3donor_count2physiological_charge-1formal_charge0Phosphonate and phosphinate metabolismec00440methylphosphonate degradation IThe 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.PW002065Metabolicmethylphosphonate degradationPWY0-1533Specdb::CMs137860Specdb::CMs145594Specdb::NmrOneD76592Specdb::NmrOneD76593Specdb::NmrOneD76594Specdb::NmrOneD76595Specdb::NmrOneD76596Specdb::NmrOneD76597Specdb::NmrOneD76598Specdb::NmrOneD76599Specdb::NmrOneD76600Specdb::NmrOneD76601Specdb::NmrOneD76602Specdb::NmrOneD76603Specdb::NmrOneD76604Specdb::NmrOneD76605Specdb::NmrOneD76606Specdb::NmrOneD76607Specdb::NmrOneD76608Specdb::NmrOneD76609Specdb::NmrOneD76610Specdb::NmrOneD76611Specdb::MsMs24593Specdb::MsMs24594Specdb::MsMs24595Specdb::MsMs31151Specdb::MsMs31152Specdb::MsMs31153Specdb::MsMs2273241Specdb::MsMs2273242Specdb::MsMs2273243Specdb::MsMs3069150Specdb::MsMs3069151Specdb::MsMs30691521381813220C2039645129CPD0-1068PPMKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnLP16679PHNL_ECOLIphnLhttp://ecmdb.ca/proteins/P16679.xmlAlpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnIP16687PHNI_ECOLIphnIhttp://ecmdb.ca/proteins/P16687.xmlAlpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnHP16686PHNH_ECOLIphnHhttp://ecmdb.ca/proteins/P16686.xmlAlpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnGP16685PHNG_ECOLIphnGhttp://ecmdb.ca/proteins/P16685.xmlPutative phosphonates transport system permease protein phnEP16683PHNE_ECOLIphnEhttp://ecmdb.ca/proteins/P16683.xmlAlpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnGP16685PHNG_ECOLIphnGhttp://ecmdb.ca/proteins/P16685.xmlMethylphosphonate + Adenosine triphosphate > α-D-ribose-1-methylphosphonate-5-triphosphate + AdenineRXN0-6732Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + AdenineR10185 Methylphosphonate + Adenosine triphosphate > Adenine + alpha-D-Ribose 1-methylphosphonate 5-triphosphatePW_R006035Adenosine triphosphate + Methylphosphonate <> alpha-D-Ribose 1-methylphosphonate 5-triphosphate + Adenine