2.0 2012-05-31 14:31:58 -0600 2015-09-17 15:42:09 -0600 ECMDB20184 M2MDB001030 Propanoyl phosphate Propanoyl phosphate is an alkylphosphate. It is generated during the course of threonine degradation via propanoyl-CoA. The first reaction in the anaerobic threonine dehydratase pathway is catalyzed by catabolic threonine dehydratase which degrades threonine to 2-oxobutanoate (alpha-ketobutyrate) and ammonia. The 2-oxobutanoate then undergoes lyase cleavage with the addition of coenzyme A to form propanoyl-CoA and formate. Once propanoyl-CoA is formed, it is processed via propionyl-phosphate to propionate in a reaction sequence that produces ATP. Acetate kinase AckA can also utilize propionate as a substrate in the final reaction. The enzymes in this pathway are also able to process L-serine, with pyruvate as the final product [EcoCyc]. Propanoyl phosphoric acid Propanoyl-P Propionyl phosphate Propionyl phosphoric acid Propionyl-P Propionyl-phosphate Propionyl-phosphoric acid C3H5O5P 152.043 151.988557419 (propanoyloxy)phosphonic acid propionyl phosphate 121-69-7 CCC(=O)OP([O-])([O-])=O InChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2 FMNMEQSRDWIBFO-UHFFFAOYSA-L Solid Cytosol logp -0.32 ALOGPS logs -0.88 ALOGPS solubility 2.01e+01 g/l ALOGPS melting_point 2.5 oC logp -0.18 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -7.4 ChemAxon iupac (propanoyloxy)phosphonic acid ChemAxon average_mass 152.043 ChemAxon mono_mass 151.988557419 ChemAxon smiles CCC(=O)OP([O-])([O-])=O ChemAxon formula C3H5O5P ChemAxon inchi InChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2 ChemAxon inchikey FMNMEQSRDWIBFO-UHFFFAOYSA-L ChemAxon polar_surface_area 83.83 ChemAxon refractivity 28.43 ChemAxon polarizability 11.82 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon C5-Branched dibasic acid metabolism ec00660 Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic threonine degradation I PWY-5437 Specdb::MsMs 25523 Specdb::MsMs 25524 Specdb::MsMs 25525 Specdb::MsMs 32081 Specdb::MsMs 32082 Specdb::MsMs 32083 1034 1007 C02876 16269 PROPIONYL-P 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 Acetate kinase P0A6A3 ACKA_ECOLI ackA http://ecmdb.ca/proteins/P0A6A3.xml Phosphate acetyltransferase P0A9M8 PTA_ECOLI pta http://ecmdb.ca/proteins/P0A9M8.xml Propionate kinase P11868 TDCD_ECOLI tdcD http://ecmdb.ca/proteins/P11868.xml Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate R00921 PTAALT-RXN ADP + Propanoyl phosphate <> Adenosine triphosphate + Propionic acid R01353 PROPKIN-RXN Propionyl-CoA + Phosphate <> Propanoyl phosphate + Coenzyme A R00921 Adenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphate R01353 Adenosine triphosphate + Propionic acid > ADP + Propanoyl phosphate Propionyl-CoA + Phosphate + Propionyl-CoA > Coenzyme A + propanoyl phosphate + Propanoyl phosphate PW_R003494 Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acid PW_R003495 Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate