2.02012-05-31 14:39:38 -06002015-06-03 17:19:48 -0600ECMDB20330M2MDB001164PhenylphosphonatePhenylphosphonate is a member of the chemical class known as Phenylphosphines and Derivatives. These are compounds containing a phenylphosphine, which consists of phosphine substituent bound to a phenyl group. . 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. BenzenephosphonateBenzenephosphonic acidPhenyl-PhosphonatePhenyl-Phosphonic acidPhenylphosphonic acidPHPNC6H5O3P156.0759155.997630538phenylphosphonatephenylphosphonate1571-33-1[O-]P([O-])(=O)C1=CC=CC=C1InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2QLZHNIAADXEJJP-UHFFFAOYSA-LSolidOuter membraneInner membranelogp0.68logs-1.02solubility1.84e+01 g/lmelting_point163-166 oClogp0.48pka_strongest_acidic1.85iupacphenylphosphonateaverage_mass156.0759mono_mass155.997630538smiles[O-]P([O-])(=O)C1=CC=CC=C1formulaC6H5O3PinchiInChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2inchikeyQLZHNIAADXEJJP-UHFFFAOYSA-Lpolar_surface_area63.19refractivity35polarizability12.92rotatable_bond_count1acceptor_count3donor_count0physiological_charge-1formal_charge-2Specdb::NmrOneD248948Specdb::NmrOneD248949Specdb::NmrOneD248950Specdb::NmrOneD248951Specdb::NmrOneD248952Specdb::NmrOneD248953Specdb::NmrOneD248954Specdb::NmrOneD248955Specdb::NmrOneD248956Specdb::NmrOneD248957Specdb::NmrOneD248958Specdb::NmrOneD248959Specdb::NmrOneD248960Specdb::NmrOneD248961Specdb::NmrOneD248962Specdb::NmrOneD248963Specdb::NmrOneD248964Specdb::NmrOneD248965Specdb::NmrOneD248966Specdb::NmrOneD248967Specdb::MsMs26987Specdb::MsMs26988Specdb::MsMs26989Specdb::MsMs33545Specdb::MsMs33546Specdb::MsMs3354751947794366324CPD0-1078Keseler, 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-D590.21097882Putative phosphonates transport system permease protein phnEP16683PHNE_ECOLIphnEhttp://ecmdb.ca/proteins/P16683.xml