2.0 2012-05-31 14:39:28 -0600 2015-06-03 17:19:48 -0600 ECMDB20327 M2MDB001161 Ethylphosphonate Ethylphosphonate 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. phosphonoacetaldehyde is catalyzed by phosphonoacetaldehyde hydrolase. This is the first nucleic sequence report of the phosphonoacetaldehyde hydrolase, an enzyme involved in the carbon-phosphorus bond cleavage. (PMID 9332393). 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. 2-Phosphonoacetaldehyde EPN Ethylphosphonic acid Phosphonoacetaldehyde C2H6O3P 109.041 109.00545557 hydrogen ethylphosphonate hydrogen ethylphosphonate 6779-09-5 CCP(O)([O-])=O InChI=1S/C2H7O3P/c1-2-6(3,4)5/h2H2,1H3,(H2,3,4,5)/p-1 GATNOFPXSDHULC-UHFFFAOYSA-M Cytoplasm Periplasm logp -0.78 ALOGPS logs -0.47 ALOGPS solubility 4.34e+01 g/l ALOGPS logp -0.83 ChemAxon pka_strongest_acidic 1.82 ChemAxon iupac hydrogen ethylphosphonate ChemAxon average_mass 109.041 ChemAxon mono_mass 109.00545557 ChemAxon smiles CCP(O)([O-])=O ChemAxon formula C2H6O3P ChemAxon inchi InChI=1S/C2H7O3P/c1-2-6(3,4)5/h2H2,1H3,(H2,3,4,5)/p-1 ChemAxon inchikey GATNOFPXSDHULC-UHFFFAOYSA-M ChemAxon polar_surface_area 60.36 ChemAxon refractivity 20.93 ChemAxon polarizability 8.48 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Microbial metabolism in diverse environments ec01120 Phosphonate and phosphinate metabolism ec00440 Specdb::NmrOneD 291475 Specdb::NmrOneD 291476 Specdb::NmrOneD 291477 Specdb::NmrOneD 291478 Specdb::NmrOneD 291479 Specdb::NmrOneD 291480 Specdb::NmrOneD 291481 Specdb::NmrOneD 291482 Specdb::NmrOneD 291483 Specdb::NmrOneD 291484 Specdb::NmrOneD 291485 Specdb::NmrOneD 291486 Specdb::NmrOneD 291487 Specdb::NmrOneD 291488 Specdb::NmrOneD 291489 Specdb::NmrOneD 291490 Specdb::NmrOneD 291491 Specdb::NmrOneD 291492 Specdb::NmrOneD 291493 Specdb::NmrOneD 291494 Specdb::MsMs 24815 Specdb::MsMs 24816 Specdb::MsMs 24817 Specdb::MsMs 31373 Specdb::MsMs 31374 Specdb::MsMs 31375 21680364 10297570 18124 CPD0-1075 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Dumora, C., Marche, M., Doignon, F., Aigle, M., Cassaigne, A., Crouzet, M. (1997). "First characterization of the phosphonoacetaldehyde hydrolase gene of Pseudomonas aeruginosa." Gene 197:405-412. 9332393 Putative phosphonates transport system permease protein phnE P16683 PHNE_ECOLI phnE http://ecmdb.ca/proteins/P16683.xml