2.0 2012-05-31 13:03:19 -0600 2015-06-03 15:53:39 -0600 ECMDB01005 M2MDB000223 (S)-Ureidoglycolic acid (S)-Ureidoglycolic acid is a substrate of enzyme ureidoglycolate dehydrogenase [EC 1.1.1.154] in purine metabolism pathway (KEGG). Enteric bacteria such as E. coli are able to utilize allantoin as a sole source of nitrogen under anaerobic conditions, but cannot 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. Ureidoglycine spontaneously converts to Ureidoglycolate. 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. (-)-Ureidoglycolate (-)-Ureidoglycolic acid (S)-Ureidoglycolate (S)-Ureidoglycolic acid (S)-[(aminocarbonyl)amino]hydroxy-acetate (S)-[(aminocarbonyl)amino]hydroxy-acetic acid <i>S</i>-ureidoglycolate S-(-)-Ureidoglycolate S-(-)-Ureidoglycolic acid S-Ureidoglycolate S-Ureidoglycolic acid Ureidoglycolate Ureidoglycolic acid C3H6N2O4 134.0907 134.03275669 (2S)-2-(carbamoylamino)-2-hydroxyacetic acid ureidoglycolate 7424-03-5 NC(=O)N[C@@H](O)C(O)=O InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1 NWZYYCVIOKVTII-SFOWXEAESA-N Solid Cytosol logp -2.06 ALOGPS logs -0.30 ALOGPS solubility 6.79e+01 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 2.94 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac (2S)-2-(carbamoylamino)-2-hydroxyacetic acid ChemAxon average_mass 134.0907 ChemAxon mono_mass 134.03275669 ChemAxon smiles NC(=O)N[C@@H](O)C(O)=O ChemAxon formula C3H6N2O4 ChemAxon inchi InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1 ChemAxon inchikey NWZYYCVIOKVTII-SFOWXEAESA-N ChemAxon polar_surface_area 112.65 ChemAxon refractivity 25.32 ChemAxon polarizability 10.8 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Microbial metabolism in diverse environments ec01120 glycolate and glyoxylate degradation Glycolic acid is introduced into the cytoplasm through either a glycolate / lactate:H+ symporter or a acetate / glycolate transporter. Once inside, glycolic acid reacts with an oxidized electron-transfer flavoprotein through a glycolate oxidase resulting in a reduced acceptor and glyoxylic acid. Glyoxylic acid can also be obtained from the introduction of glyoxylic acid. It can also be obtained from the metabolism of (S)-allantoin. S-allantoin is introduced into the cytoplasm through a purine and pyrimidine transporter(allantoin specific). Once inside, the compound reacts with water through a allantoinase resulting in hydrogen ion and allantoic acid. Allantoic acid then reacts with water and hydrogen ion through a allantoate amidohydrolase resulting in a carbon dioxide, ammonium and S-ureidoglycine. The latter compound reacts with water through a S-ureidoglycine aminohydrolase resulting in ammonium and S-ureidoglycolic acid which in turn reacts with a Ureidoglycolate lyase resulting in urea and glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase. PW000827 Metabolic 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 allantoin degradation to ureidoglycolate II (ammonia producing) PWY-5698 allantoin degradation to glyoxylate III PWY-5705 Specdb::CMs 2342 Specdb::CMs 37887 Specdb::CMs 173408 Specdb::NmrOneD 21122 Specdb::NmrOneD 21123 Specdb::NmrOneD 21124 Specdb::NmrOneD 21125 Specdb::NmrOneD 21126 Specdb::NmrOneD 21127 Specdb::NmrOneD 21128 Specdb::NmrOneD 21129 Specdb::NmrOneD 21130 Specdb::NmrOneD 21131 Specdb::NmrOneD 21132 Specdb::NmrOneD 21133 Specdb::NmrOneD 21134 Specdb::NmrOneD 21135 Specdb::NmrOneD 21136 Specdb::NmrOneD 21137 Specdb::NmrOneD 21138 Specdb::NmrOneD 21139 Specdb::NmrOneD 21140 Specdb::NmrOneD 21141 Specdb::MsMs 29192 Specdb::MsMs 29193 Specdb::MsMs 29194 Specdb::MsMs 35750 Specdb::MsMs 35751 Specdb::MsMs 35752 Specdb::MsMs 2360129 Specdb::MsMs 2360130 Specdb::MsMs 2360131 Specdb::MsMs 2606251 Specdb::MsMs 2606252 Specdb::MsMs 2606253 HMDB01005 439269 388403 C00603 15412 CPD-1091 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 Allantoate amidohydrolase P77425 ALLC_ECOLI allC http://ecmdb.ca/proteins/P77425.xml Ureidoglycolate dehydrogenase P77555 ALLD_ECOLI allD http://ecmdb.ca/proteins/P77555.xml Ureidoglycolate hydrolase P77731 ALLA_ECOLI allA http://ecmdb.ca/proteins/P77731.xml conserved protein P75713 ylbA http://ecmdb.ca/proteins/P75713.xml 2 Hydrogen ion + Water + (S)-Ureidoglycolic acid > Carbon dioxide + Glyoxylic acid +2 Ammonium Allantoic acid + 2 Hydrogen ion + 2 Water > Carbon dioxide +2 Ammonium + (S)-Ureidoglycolic acid NAD + (S)-Ureidoglycolic acid <> Hydrogen ion + NADH + Oxalureate R02935 (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide R00469 (S)-Ureidoglycolic acid + NADP <> Oxalureate + NADPH + Hydrogen ion R02936 Ureidoglycine + Water <> (S)-Ureidoglycolic acid + Ammonia R05554 NAD(P)⁺ + (S)-Ureidoglycolic acid > NAD(P)H + Oxalureate + Hydrogen ion R165-RXN (S)-Ureidoglycolic acid > Urea + Glyoxylic acid UREIDOGLYCOLATE-LYASE-RXN (S)-Ureidoglycolic acid + Water > Glyoxylic acid +2 Ammonia + Carbon dioxide (S)-Ureidoglycolic acid + NAD(P)(+) > Oxalureate + NAD(P)H (S)-Ureidoglycolic acid <> Glyoxylic acid + Urea R00776 (S)-Ureidoglycolic acid + NAD + NADP <> Oxalureate + NADH + NADPH + Hydrogen ion R02935 R02936 S-ureidoglycine + Water > Ammonium + (S)-Ureidoglycolic acid PW_R002987 (S)-Ureidoglycolic acid + NAD > Hydrogen ion + NADH + Oxalureate PW_R005987 (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide (S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxide