2.0 2012-07-30 14:55:09 -0600 2015-06-03 17:21:02 -0600 ECMDB21261 M2MDB001669 Oxamate Oxamate is an amino-substituted glyoxylic acid derivative. It is believed to be a product of Allantoin degradation in E. coli. Enteric bacteria such as E. coli are able to utilize allantoin as a sole source of nitrogen under anaerobic conditions, but can not utilize it as a sole source of carbon. The first step in allantoin degradation is the opening of the aromatic ring, yielding allantoate, performed by allantoinase. In the next step allantoate is hydrolyzed to S-ureidoglycine by allantoate amidohydrolase. Ureidoglycolate dehydrogenase then oxidizes ureidoglycolate to oxalurate. It is believed oxalurate is converted into oxamate and carbamoyl-phosphate, which can be further metabolized to CO2, ammonia and ATP. (aminocarbonyl)-Formate (aminocarbonyl)-Formic acid (aminocarbonyl)-Oxamate (Aminocarbonyl)-oxamic acid 2-Oxo-Glycine Amino(oxo)acetate Amino(oxo)acetic acid Amino-Glyoxylate Amino-Glyoxylic acid Aminooxo-Acetate Aminooxo-Acetic acid Carbamoyl-Formate Carbamoyl-Formic acid Iodoxamate meglumine (USAN) Iodoxamic acid meglumine (USAN) OA (VAN) Oxalamate Oxalamic acid Oxalate monoamide Oxalic acid monoamide Oxalic monoamide Oxamate Oxamic acid Oxamidate Oxamidic acid C2H3NO3 89.0501 89.011292967 carbamoylformic acid oxamic acid 471-47-6 NC(=O)C(O)=O InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6) SOWBFZRMHSNYGE-UHFFFAOYSA-N Solid Cytosol logp -1.44 ALOGPS logs 0.08 ALOGPS solubility 1.08e+02 g/l ALOGPS melting_point 210 oC logp -1.1 ChemAxon pka_strongest_acidic 2.49 ChemAxon pka_strongest_basic -6.2 ChemAxon iupac carbamoylformic acid ChemAxon average_mass 89.0501 ChemAxon mono_mass 89.011292967 ChemAxon smiles NC(=O)C(O)=O ChemAxon formula C2H3NO3 ChemAxon inchi InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6) ChemAxon inchikey SOWBFZRMHSNYGE-UHFFFAOYSA-N ChemAxon polar_surface_area 80.39 ChemAxon refractivity 16.26 ChemAxon polarizability 6.65 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon allantoin degradation (anaerobic) Allantoin can be degraded in anaerobic conditions. The first step involves allantoin being degraded by an allantoinase resulting in an allantoate. This compound in turn is metabolized by reacting with water and 2 hydrogen ions through an allantoate amidohydrolase resulting in the release of a carbon dioxide, ammonium and an S-ureidoglycine. The latter compund is further degrades through a S-ureidoglycine aminohydrolase resulting in the release of an ammonium and an S-ureidoglycolate. S-ureidoglycolate can be metabolized into oxalurate by two different reactions. The first reactions involves a NAD driven ureidoglycolate dehydrogenase resulting in the release of a hydrogen ion , an NADH and a oxalurate. On the other hand S-ureidoglycolate can react with NADP resulting in the release of an NADPH, a hydroge ion and an oxalurate. It is hypothesized that oxalurate can interact with a phosphate and release a a carbamoyl phosphate and an oxamate. The carbamoyl phosphate can be further degraded by reacting with an ADP, and a hydrogen ion through a carbamate kinase resulting in the release of an ammonium , ATP and carbon dioxide PW002050 Metabolic allantoin degradation IV (anaerobic) PWY0-41 Specdb::CMs 983 Specdb::CMs 30660 Specdb::CMs 31948 Specdb::NmrOneD 332042 Specdb::NmrOneD 332043 Specdb::NmrOneD 332044 Specdb::NmrOneD 332045 Specdb::NmrOneD 332046 Specdb::NmrOneD 332047 Specdb::NmrOneD 332048 Specdb::NmrOneD 332049 Specdb::NmrOneD 332050 Specdb::NmrOneD 332051 Specdb::NmrOneD 332052 Specdb::NmrOneD 332053 Specdb::NmrOneD 332054 Specdb::NmrOneD 332055 Specdb::NmrOneD 332056 Specdb::NmrOneD 332057 Specdb::NmrOneD 332058 Specdb::NmrOneD 332059 Specdb::NmrOneD 332060 Specdb::NmrOneD 332061 Specdb::MsMs 23624 Specdb::MsMs 23625 Specdb::MsMs 23626 Specdb::MsMs 30422 Specdb::MsMs 30423 Specdb::MsMs 30424 Specdb::MsMs 438224 Specdb::MsMs 438225 Specdb::MsMs 438226 974 949 C01444 18058 OXAMATE OXM 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 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 Oxamate + Carbamoylphosphate < Phosphate + Oxalureate OXAMATE-CARBAMOYLTRANSFERASE-RXN