2.0 2012-10-10 12:16:59 -0600 2015-06-03 17:25:56 -0600 ECMDB23108 M2MDB003498 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate is an intermediate in purine degradataion. It is a byproduct of 5-hydroxyisurate metabolism. It is generated by the enzyme hydroxyisourate hydrolase which catalyzes the reaction 5-hydroxyisourate + H2O <=> 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate. In most organisms, including some bacteria (such as E. coli), plants, and certain animals, urate is metabolized via a common pathway, producing the stereospecific form S-allantoin as the final product. In the first step of the pathway factor-independent urate hydroxylase catalyzes the conversion of urate to 5-hydroxyisourate. 5-hydroxyisourate is relatively unstable, and often decomposes in vitro to yield racemic allantoin. Hydroxyisourate hydrolase catalyzes the hydrolysis of the N1-C6 bond of 5-hydroxyisourate to form 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylate. 2-oxo-4-Hydroxy-4-carboxy-5-ureidoimidazoline 4-(carbamoylamino)-5-Hydroxy-2-oxo-1H-imidazole-5-carboxylate 4-(carbamoylamino)-5-hydroxy-2-oxo-1H-imidazole-5-carboxylic acid 4-(carbamoylamino)-5-Hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylate 4-(Carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylic acid C5H6N4O5 202.1249 202.033819322 4-(carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid 5-(carbamoylamino)-4-hydroxy-2-oxo-3H-imidazole-4-carboxylic acid NC(=O)NC1=NC(=O)NC1(O)C(O)=O InChI=1S/C5H6N4O5/c6-3(12)7-1-5(14,2(10)11)9-4(13)8-1/h14H,(H,10,11)(H4,6,7,8,9,12,13) WHKYNCPIXMNTRQ-UHFFFAOYSA-N logp -1.86 ALOGPS logs -1.62 ALOGPS solubility 4.85e+00 g/l ALOGPS logp -2.3 ChemAxon pka_strongest_acidic 2.53 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 4-(carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid ChemAxon average_mass 202.1249 ChemAxon mono_mass 202.033819322 ChemAxon smiles NC(=O)NC1=NC(=O)NC1(O)C(O)=O ChemAxon formula C5H6N4O5 ChemAxon inchi InChI=1S/C5H6N4O5/c6-3(12)7-1-5(14,2(10)11)9-4(13)8-1/h14H,(H,10,11)(H4,6,7,8,9,12,13) ChemAxon inchikey WHKYNCPIXMNTRQ-UHFFFAOYSA-N ChemAxon polar_surface_area 154.11 ChemAxon refractivity 38.67 ChemAxon polarizability 16 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 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 Specdb::CMs 34138 Specdb::CMs 47851 Specdb::MsMs 26513 Specdb::MsMs 26514 Specdb::MsMs 26515 Specdb::MsMs 33071 Specdb::MsMs 33072 Specdb::MsMs 33073 Specdb::MsMs 3597860 Specdb::MsMs 3597861 Specdb::MsMs 3597862 Specdb::MsMs 3597863 Specdb::MsMs 3597864 Specdb::MsMs 3597865 443736 C12248 31132 Hydroxyisourate hydrolase P76341 hiuH http://ecmdb.ca/proteins/P76341.xml 5-Hydroxyisourate + Water > 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate R06601 5-Hydroxyisourate + Water + 5-Hydroxyisourate <> 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate + 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate R06601