2.0 2012-05-31 14:39:38 -0600 2015-06-03 17:19:48 -0600 ECMDB20330 M2MDB001164 Phenylphosphonate Phenylphosphonate 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. Benzenephosphonate Benzenephosphonic acid Phenyl-Phosphonate Phenyl-Phosphonic acid Phenylphosphonic acid PHPN C6H5O3P 156.0759 155.997630538 phenylphosphonate phenylphosphonate 1571-33-1 [O-]P([O-])(=O)C1=CC=CC=C1 InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2 QLZHNIAADXEJJP-UHFFFAOYSA-L Solid Outer membrane Inner membrane logp 0.68 ALOGPS logs -1.02 ALOGPS solubility 1.84e+01 g/l ALOGPS melting_point 163-166 oC logp 0.48 ChemAxon pka_strongest_acidic 1.85 ChemAxon iupac phenylphosphonate ChemAxon average_mass 156.0759 ChemAxon mono_mass 155.997630538 ChemAxon smiles [O-]P([O-])(=O)C1=CC=CC=C1 ChemAxon formula C6H5O3P ChemAxon inchi InChI=1S/C6H7O3P/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H2,7,8,9)/p-2 ChemAxon inchikey QLZHNIAADXEJJP-UHFFFAOYSA-L ChemAxon polar_surface_area 63.19 ChemAxon refractivity 35 ChemAxon polarizability 12.92 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -2 ChemAxon Specdb::NmrOneD 248948 Specdb::NmrOneD 248949 Specdb::NmrOneD 248950 Specdb::NmrOneD 248951 Specdb::NmrOneD 248952 Specdb::NmrOneD 248953 Specdb::NmrOneD 248954 Specdb::NmrOneD 248955 Specdb::NmrOneD 248956 Specdb::NmrOneD 248957 Specdb::NmrOneD 248958 Specdb::NmrOneD 248959 Specdb::NmrOneD 248960 Specdb::NmrOneD 248961 Specdb::NmrOneD 248962 Specdb::NmrOneD 248963 Specdb::NmrOneD 248964 Specdb::NmrOneD 248965 Specdb::NmrOneD 248966 Specdb::NmrOneD 248967 Specdb::MsMs 26987 Specdb::MsMs 26988 Specdb::MsMs 26989 Specdb::MsMs 33545 Specdb::MsMs 33546 Specdb::MsMs 33547 5194779 4366324 CPD0-1078 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 Putative phosphonates transport system permease protein phnE P16683 PHNE_ECOLI phnE http://ecmdb.ca/proteins/P16683.xml