2.0 2012-05-31 10:26:49 -0600 2015-09-13 12:56:08 -0600 ECMDB00462 M2MDB000139 Allantoin Allantoin is a member of the chemical class known as Ureides. These are compounds containing an ureide group with the general structure R-CO-NH-CO-N(R)R'', formally derived by the acylation of urea. It is also called 5-ureidohydantoin or glyoxyldiureide. It is a diureide of glyoxylic acid. Allantoin is a compound involved in purine metabolism. It has two forms, (S)(+)-Allantoin and (R)(-)-Allantoin, though only the S form is found in E.coli. 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. (PMID 10601204). (S)-allantoin 2,5-Dioxo-4-imidazolidinyl-urea 4-Ureido-2,5-Imidazolidinedione 5-Ureido-Hydantoin 5-Ureidohydantoin 5-Ureidohydrantoin Alantan Allantoin Allantoin (JAN/USP) Allantol Alloxantin AVC/Dienestrolcream Cordianine D00121 Fancol TOIN Glyoxyldiureid Glyoxyldiureide Glyoxylic diureide N-(2,5-Dioxo-4-imidazolidinyl)urea Psoralon Sebical Septalan C4H6N4O3 158.1154 158.043990078 (2,5-dioxoimidazolidin-4-yl)urea allantoin 97-59-6 NC(=O)NC1NC(=O)NC1=O InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) POJWUDADGALRAB-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.95 ALOGPS logs -1.52 ALOGPS solubility 4.73e+00 g/l ALOGPS melting_point 239 oC logp -2.4 ChemAxon pka_strongest_acidic 7.95 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac (2,5-dioxoimidazolidin-4-yl)urea ChemAxon average_mass 158.1154 ChemAxon mono_mass 158.043990078 ChemAxon smiles NC(=O)NC1NC(=O)NC1=O ChemAxon formula C4H6N4O3 ChemAxon inchi InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11) ChemAxon inchikey POJWUDADGALRAB-UHFFFAOYSA-N ChemAxon polar_surface_area 113.32 ChemAxon refractivity 32.02 ChemAxon polarizability 12.89 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 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 Specdb::CMs 552 Specdb::CMs 553 Specdb::CMs 554 Specdb::CMs 1583 Specdb::CMs 1603 Specdb::CMs 1778 Specdb::CMs 3309 Specdb::CMs 27359 Specdb::CMs 29056 Specdb::CMs 30476 Specdb::CMs 30477 Specdb::CMs 31149 Specdb::CMs 31150 Specdb::CMs 31151 Specdb::CMs 123555 Specdb::CMs 167488 Specdb::EiMs 866 Specdb::NmrOneD 1233 Specdb::NmrOneD 1380 Specdb::NmrOneD 4792 Specdb::NmrOneD 4793 Specdb::NmrOneD 144050 Specdb::NmrOneD 144051 Specdb::NmrOneD 144052 Specdb::NmrOneD 144053 Specdb::NmrOneD 144054 Specdb::NmrOneD 144055 Specdb::NmrOneD 144056 Specdb::NmrOneD 144057 Specdb::NmrOneD 144058 Specdb::NmrOneD 144059 Specdb::NmrOneD 144060 Specdb::NmrOneD 144061 Specdb::NmrOneD 144062 Specdb::NmrOneD 144063 Specdb::NmrOneD 144064 Specdb::NmrOneD 144065 Specdb::NmrOneD 144066 Specdb::NmrOneD 144067 Specdb::NmrOneD 144068 Specdb::NmrOneD 144069 Specdb::NmrOneD 166437 Specdb::MsMs 671 Specdb::MsMs 672 Specdb::MsMs 673 Specdb::MsMs 4078 Specdb::MsMs 4079 Specdb::MsMs 20090 Specdb::MsMs 20091 Specdb::MsMs 20092 Specdb::MsMs 20444 Specdb::MsMs 20445 Specdb::MsMs 20446 Specdb::MsMs 21035 Specdb::MsMs 21036 Specdb::MsMs 21037 Specdb::MsMs 21104 Specdb::MsMs 21105 Specdb::MsMs 21106 Specdb::MsMs 21641 Specdb::MsMs 21642 Specdb::MsMs 21643 Specdb::MsMs 21995 Specdb::MsMs 21996 Specdb::MsMs 21997 Specdb::MsMs 22586 Specdb::MsMs 22587 Specdb::NmrTwoD 1324 HMDB00462 199 C01551 15676 ALLANTOIN Allantoin Keseler, I. 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A potential index of free-radical reactions in vivo? Biochem J. 1987 May 1;243(3):803-8. 3663100 http://hmdb.ca/system/metabolites/msds/000/000/381/original/HMDB00462.pdf?1358893321 Allantoinase P77671 ALLB_ECOLI allB http://ecmdb.ca/proteins/P77671.xml Putative allantoin permease P75712 ALLP_ECOLI ybbW http://ecmdb.ca/proteins/P75712.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Allantoin + Water > Allantoic acid + Hydrogen ion