2.0 2012-05-31 14:39:35 -0600 2015-06-03 17:19:48 -0600 ECMDB20329 M2MDB001163 3-Aminopropylphosphonate 3-aminopropylphosphonate 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. 3-(Hydroxy-oxido-phosphoryl)propylazanium 3-Aminopropylphosphonate 3-Aminopropylphosphonic acid 3-APPn C3H10NO3P 139.0902 139.039829703 (3-aminopropyl)phosphonic acid 3-aminopropylphosphonic acid NCCCP(O)(O)=O InChI=1S/C3H10NO3P/c4-2-1-3-8(5,6)7/h1-4H2,(H2,5,6,7) GSZQTIFGANBTNF-UHFFFAOYSA-N Cytoplasm Periplasm logp -1.41 ALOGPS logs -0.55 ALOGPS solubility 3.89e+01 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 1.79 ChemAxon pka_strongest_basic 10.22 ChemAxon iupac (3-aminopropyl)phosphonic acid ChemAxon average_mass 139.0902 ChemAxon mono_mass 139.039829703 ChemAxon smiles NCCCP(O)(O)=O ChemAxon formula C3H10NO3P ChemAxon inchi InChI=1S/C3H10NO3P/c4-2-1-3-8(5,6)7/h1-4H2,(H2,5,6,7) ChemAxon inchikey GSZQTIFGANBTNF-UHFFFAOYSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 30.12 ChemAxon polarizability 12.15 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic Specdb::CMs 108251 Specdb::CMs 120778 Specdb::NmrOneD 202487 Specdb::NmrOneD 202488 Specdb::NmrOneD 202489 Specdb::NmrOneD 202490 Specdb::NmrOneD 202491 Specdb::NmrOneD 202492 Specdb::NmrOneD 202493 Specdb::NmrOneD 202494 Specdb::NmrOneD 202495 Specdb::NmrOneD 202496 Specdb::NmrOneD 202497 Specdb::NmrOneD 202498 Specdb::NmrOneD 202499 Specdb::NmrOneD 202500 Specdb::NmrOneD 202501 Specdb::NmrOneD 202502 Specdb::NmrOneD 202503 Specdb::NmrOneD 202504 Specdb::NmrOneD 202505 Specdb::NmrOneD 202506 Specdb::MsMs 28109 Specdb::MsMs 28110 Specdb::MsMs 28111 Specdb::MsMs 34667 Specdb::MsMs 34668 Specdb::MsMs 34669 Specdb::MsMs 3402928 Specdb::MsMs 3402929 Specdb::MsMs 3402930 Specdb::MsMs 3402931 Specdb::MsMs 3402932 Specdb::MsMs 3402933 4868255 88080 CPD0-1077 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 Phosphonates import ATP-binding protein PhnC P16677 PHNC_ECOLI phnC http://ecmdb.ca/proteins/P16677.xml Putative phosphonates transport system permease protein phnE P16683 PHNE_ECOLI phnE http://ecmdb.ca/proteins/P16683.xml Phosphonates import ATP-binding protein PhnC P16677 PHNC_ECOLI phnC http://ecmdb.ca/proteins/P16677.xml Phosphonates-binding periplasmic protein P16682 PHND_ECOLI phnD http://ecmdb.ca/proteins/P16682.xml 3-Aminopropylphosphonate + Adenosine triphosphate + Water > ADP + Phosphate + Hydrogen ion PW_RCT000180