2.0 2012-05-31 14:31:48 -0600 2015-06-03 17:19:28 -0600 ECMDB20181 M2MDB001027 Oxalureate Oxalureate is a member of the chemical class known as Isoureas. These are organic compounds containing the isourea group, with the general structure RN(R')C(=NR'')OR''', or its hydrocarbyl derivatives (R,R',R'',R'''=H, alkyl, aryl). ((aminocarbonyl)amino)oxo-Acetate ((aminocarbonyl)amino)oxo-Acetic acid Carbamoylamino(oxo)acetate Carbamoylamino(oxo)acetic acid Carbamoyloxamate Carbamoyloxamic acid Carbamyl oxamate Carbamyl oxamic acid Monooxalylurea Onooxalylurea OXAL Oxalate Oxalic acid Oxalurate Oxalureate Oxalureic acid Oxaluric acid Ureido(oxo)acetate Ureido(oxo)acetic acid [(aminocarbonyl)amino]oxo-Acetate [(aminocarbonyl)amino]oxo-Acetic acid C3H4N2O4 132.0749 132.017106626 2-hydroxy-2-[(C-hydroxycarbonimidoyl)imino]acetic acid oxalureate 585-05-7 OC(=N)N=C(O)C(O)=O InChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9) UWBHMRBRLOJJAA-UHFFFAOYSA-N Cytosol logp -0.95 ALOGPS logs -1.89 ALOGPS solubility 1.71e+00 g/l ALOGPS logp -0.83 ChemAxon pka_strongest_acidic 2.67 ChemAxon pka_strongest_basic 2.25 ChemAxon iupac 2-hydroxy-2-[(C-hydroxycarbonimidoyl)imino]acetic acid ChemAxon average_mass 132.0749 ChemAxon mono_mass 132.017106626 ChemAxon smiles OC(=N)N=C(O)C(O)=O ChemAxon formula C3H4N2O4 ChemAxon inchi InChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9) ChemAxon inchikey UWBHMRBRLOJJAA-UHFFFAOYSA-N ChemAxon polar_surface_area 113.97 ChemAxon refractivity 35.96 ChemAxon polarizability 10.18 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Microbial metabolism in diverse environments ec01120 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 1083736 Specdb::NmrOneD 328792 Specdb::NmrOneD 328793 Specdb::NmrOneD 328794 Specdb::NmrOneD 328795 Specdb::NmrOneD 328796 Specdb::NmrOneD 328797 Specdb::NmrOneD 328798 Specdb::NmrOneD 328799 Specdb::NmrOneD 328800 Specdb::NmrOneD 328801 Specdb::MsMs 27776 Specdb::MsMs 27777 Specdb::MsMs 27778 Specdb::MsMs 34334 Specdb::MsMs 34335 Specdb::MsMs 34336 Specdb::MsMs 3603893 Specdb::MsMs 3603894 Specdb::MsMs 3603895 Specdb::MsMs 3603896 Specdb::MsMs 3603897 Specdb::MsMs 3603898 456 443 C00802 16582 CPD-389 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 Ureidoglycolate dehydrogenase P77555 ALLD_ECOLI allD http://ecmdb.ca/proteins/P77555.xml NAD + (S)-Ureidoglycolic acid <> Hydrogen ion + NADH + Oxalureate R02935 (S)-Ureidoglycolic acid + NADP <> Oxalureate + NADPH + Hydrogen ion R02936 Oxamate + Carbamoylphosphate < Phosphate + Oxalureate OXAMATE-CARBAMOYLTRANSFERASE-RXN NAD(P)⁺ + (S)-Ureidoglycolic acid > NAD(P)H + Oxalureate + Hydrogen ion R165-RXN (S)-Ureidoglycolic acid + NAD(P)(+) > Oxalureate + NAD(P)H (S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ion R02935 R02936 (S)-Ureidoglycolic acid + NAD > Hydrogen ion + NADH + Oxalureate PW_R005987