2.02012-05-31 14:31:48 -06002015-06-03 17:19:28 -0600ECMDB20181M2MDB001027OxalureateOxalureate 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 acidCarbamoylamino(oxo)acetateCarbamoylamino(oxo)acetic acidCarbamoyloxamateCarbamoyloxamic acidCarbamyl oxamateCarbamyl oxamic acidMonooxalylureaOnooxalylureaOXALOxalateOxalic acidOxalurateOxalureateOxalureic acidOxaluric acidUreido(oxo)acetateUreido(oxo)acetic acid[(aminocarbonyl)amino]oxo-Acetate[(aminocarbonyl)amino]oxo-Acetic acidC3H4N2O4132.0749132.0171066262-hydroxy-2-[(C-hydroxycarbonimidoyl)imino]acetic acidoxalureate585-05-7OC(=N)N=C(O)C(O)=OInChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9)UWBHMRBRLOJJAA-UHFFFAOYSA-NCytosollogp-0.95logs-1.89solubility1.71e+00 g/llogp-0.83pka_strongest_acidic2.67pka_strongest_basic2.25iupac2-hydroxy-2-[(C-hydroxycarbonimidoyl)imino]acetic acidaverage_mass132.0749mono_mass132.017106626smilesOC(=N)N=C(O)C(O)=OformulaC3H4N2O4inchiInChI=1S/C3H4N2O4/c4-3(9)5-1(6)2(7)8/h(H,7,8)(H3,4,5,6,9)inchikeyUWBHMRBRLOJJAA-UHFFFAOYSA-Npolar_surface_area113.97refractivity35.96polarizability10.18rotatable_bond_count1acceptor_count6donor_count4physiological_charge-2formal_charge0Purine metabolismec00230Microbial metabolism in diverse environmentsec01120allantoin 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 dioxidePW002050Metabolicallantoin degradation IV (anaerobic)PWY0-41Specdb::CMs1083736Specdb::NmrOneD328792Specdb::NmrOneD328793Specdb::NmrOneD328794Specdb::NmrOneD328795Specdb::NmrOneD328796Specdb::NmrOneD328797Specdb::NmrOneD328798Specdb::NmrOneD328799Specdb::NmrOneD328800Specdb::NmrOneD328801Specdb::MsMs27776Specdb::MsMs27777Specdb::MsMs27778Specdb::MsMs34334Specdb::MsMs34335Specdb::MsMs34336Specdb::MsMs3603893Specdb::MsMs3603894Specdb::MsMs3603895Specdb::MsMs3603896Specdb::MsMs3603897Specdb::MsMs3603898456443C0080216582CPD-389Keseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Ureidoglycolate dehydrogenaseP77555ALLD_ECOLIallDhttp://ecmdb.ca/proteins/P77555.xmlNAD + (S)-Ureidoglycolic acid <> Hydrogen ion + NADH + OxalureateR02935(S)-Ureidoglycolic acid + NADP <> Oxalureate + NADPH + Hydrogen ionR02936Oxamate + Carbamoylphosphate < Phosphate + OxalureateOXAMATE-CARBAMOYLTRANSFERASE-RXNNAD(P)<sup>+</sup> + (S)-Ureidoglycolic acid > NAD(P)H + Oxalureate + Hydrogen ionR165-RXN(S)-Ureidoglycolic acid + NAD(P)(+) > Oxalureate + NAD(P)H(S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ionR02935 R02936 (S)-Ureidoglycolic acid + NAD > Hydrogen ion + NADH + OxalureatePW_R005987