2.0 2012-05-31 13:47:43 -0600 2015-09-13 12:56:10 -0600 ECMDB01209 M2MDB000299 Allantoic acid Allantoic acid is the END product of Allantoicase [EC:3.5.3.4], an enzyme involved in uric acid degradation (Purine metabolism). It is a crystalline acid obtained by hydrolysis of allantoin. (Wikipedia) Allantoate Allantoic acid Diureidoacetate Diureidoacetic acid C4H8N4O4 176.1307 176.054554764 2,2-bis(carbamoylamino)acetic acid allantoic acid 99-16-1 NC(=O)NC(NC(N)=O)C(O)=O InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12) NUCLJNSWZCHRKL-UHFFFAOYSA-N Solid Cytosol logp -2.12 ALOGPS logs -1.42 ALOGPS solubility 6.70e+00 g/l ALOGPS melting_point 180-181 oC logp -2.6 ChemAxon pka_strongest_acidic 3.24 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2,2-bis(carbamoylamino)acetic acid ChemAxon average_mass 176.1307 ChemAxon mono_mass 176.054554764 ChemAxon smiles NC(=O)NC(NC(N)=O)C(O)=O ChemAxon formula C4H8N4O4 ChemAxon inchi InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12) ChemAxon inchikey NUCLJNSWZCHRKL-UHFFFAOYSA-N ChemAxon polar_surface_area 147.54 ChemAxon refractivity 35.1 ChemAxon polarizability 14.59 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 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 to ureidoglycolate II (ammonia producing) PWY-5698 Specdb::CMs 708 Specdb::CMs 2466 Specdb::CMs 32303 Specdb::CMs 32304 Specdb::CMs 32305 Specdb::CMs 37976 Specdb::CMs 169155 Specdb::NmrOneD 1662 Specdb::MsMs 1466 Specdb::MsMs 1467 Specdb::MsMs 1468 Specdb::MsMs 5083 Specdb::MsMs 5084 Specdb::MsMs 5085 Specdb::MsMs 5086 Specdb::MsMs 5087 Specdb::MsMs 178200 Specdb::MsMs 178201 Specdb::MsMs 178202 Specdb::MsMs 180516 Specdb::MsMs 180517 Specdb::MsMs 180518 Specdb::MsMs 437249 Specdb::MsMs 437250 Specdb::MsMs 437251 Specdb::MsMs 437252 Specdb::MsMs 437253 Specdb::MsMs 2226835 Specdb::MsMs 2227868 Specdb::MsMs 2228485 Specdb::MsMs 2228554 Specdb::MsMs 2230873 Specdb::MsMs 2230942 Specdb::NmrTwoD 1603 HMDB01209 203 198 C00499 30837 ALLANTOATE 1AL 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Vigetti D, Pollegioni L, Monetti C, Prati M, Bernardini G, Gornati R: Property comparison of recombinant amphibian and mammalian allantoicases. FEBS Lett. 2002 Feb 13;512(1-3):323-8. 11852104 Hermanowicz, Witold. Allantoic acid. Formation of allantoic acid from allantoin. Roczniki Chemii (1948), 22 159-80. http://hmdb.ca/system/metabolites/msds/000/001/085/original/HMDB01209.pdf?1358460291 Allantoate amidohydrolase P77425 ALLC_ECOLI allC http://ecmdb.ca/proteins/P77425.xml Allantoinase P77671 ALLB_ECOLI allB http://ecmdb.ca/proteins/P77671.xml Allantoin + Water > Allantoic acid + Hydrogen ion Allantoic acid + 2 Hydrogen ion + 2 Water > Carbon dioxide +2 Ammonium + (S)-Ureidoglycolic acid Allantoic acid + Water <> Ureidoglycine + Ammonia + Carbon dioxide R02423 (S)(+)-Allantoin + Water <> Allantoic acid R02425 Hydrogen ion + Allantoic acid + Water > <i>S</i>-ureidoglycine + Ammonia + Carbon dioxide ALLANTOATE-DEIMINASE-RXN <i>S</i>-allantoin + Water > Hydrogen ion + Allantoic acid ALLANTOINASE-RXN (S)(+)-Allantoin + Water > Allantoic acid Allantoic acid + Water + 2 Hydrogen ion > Carbon dioxide + Ammonium + S-ureidoglycine PW_R002986