2.02012-05-31 13:47:43 -06002015-09-13 12:56:10 -0600ECMDB01209M2MDB000299Allantoic acidAllantoic 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)AllantoateAllantoic acidDiureidoacetateDiureidoacetic acidC4H8N4O4176.1307176.0545547642,2-bis(carbamoylamino)acetic acidallantoic acid99-16-1NC(=O)NC(NC(N)=O)C(O)=OInChI=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-NSolidCytosollogp-2.12logs-1.42solubility6.70e+00 g/lmelting_point180-181 oClogp-2.6pka_strongest_acidic3.24pka_strongest_basic-3.1iupac2,2-bis(carbamoylamino)acetic acidaverage_mass176.1307mono_mass176.054554764smilesNC(=O)NC(NC(N)=O)C(O)=OformulaC4H8N4O4inchiInChI=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)inchikeyNUCLJNSWZCHRKL-UHFFFAOYSA-Npolar_surface_area147.54refractivity35.1polarizability14.59rotatable_bond_count3acceptor_count4donor_count5physiological_charge-1formal_charge0Purine metabolismec00230Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100glycolate and glyoxylate degradationGlycolic 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.
PW000827Metabolicallantoin 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 to ureidoglycolate II (ammonia producing)PWY-5698Specdb::CMs708Specdb::CMs2466Specdb::CMs32303Specdb::CMs32304Specdb::CMs32305Specdb::CMs37976Specdb::CMs169155Specdb::NmrOneD1662Specdb::MsMs1466Specdb::MsMs1467Specdb::MsMs1468Specdb::MsMs5083Specdb::MsMs5084Specdb::MsMs5085Specdb::MsMs5086Specdb::MsMs5087Specdb::MsMs178200Specdb::MsMs178201Specdb::MsMs178202Specdb::MsMs180516Specdb::MsMs180517Specdb::MsMs180518Specdb::MsMs437249Specdb::MsMs437250Specdb::MsMs437251Specdb::MsMs437252Specdb::MsMs437253Specdb::MsMs2226835Specdb::MsMs2227868Specdb::MsMs2228485Specdb::MsMs2228554Specdb::MsMs2230873Specdb::MsMs2230942Specdb::NmrTwoD1603HMDB01209203198C0049930837ALLANTOATE1ALKeseler, 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Vigetti 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):323-8.11852104Hermanowicz, 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?1358460291Allantoate amidohydrolaseP77425ALLC_ECOLIallChttp://ecmdb.ca/proteins/P77425.xmlAllantoinaseP77671ALLB_ECOLIallBhttp://ecmdb.ca/proteins/P77671.xmlAllantoin + Water > Allantoic acid + Hydrogen ionAllantoic acid + 2 Hydrogen ion + 2 Water > Carbon dioxide +2 Ammonium + (S)-Ureidoglycolic acidAllantoic acid + Water <> Ureidoglycine + Ammonia + Carbon dioxideR02423(S)(+)-Allantoin + Water <> Allantoic acidR02425Hydrogen ion + Allantoic acid + Water > <i>S</i>-ureidoglycine + Ammonia + Carbon dioxideALLANTOATE-DEIMINASE-RXN<i>S</i>-allantoin + Water > Hydrogen ion + Allantoic acidALLANTOINASE-RXN(S)(+)-Allantoin + Water > Allantoic acidAllantoic acid + Water + 2 Hydrogen ion > Carbon dioxide + Ammonium + S-ureidoglycinePW_R002986