Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:48:12 UTC
Update Date2022-08-31 18:24:26 UTC
Metabolite IDMMDBc0031760
Metabolite Identification
Common Name5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate
Description5-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.
Structure
Synonyms
ValueSource
2-oxo-4-Hydroxy-4-carboxy-5-ureidoimidazolineKegg
5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylic acidGenerator
Molecular FormulaC5H6N4O5
Average Mass202.1249
Monoisotopic Mass202.033819322
IUPAC Name4-(carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid
Traditional Name5-(carbamoylamino)-4-hydroxy-2-oxo-3H-imidazole-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
NC(=O)NC1=NC(=O)NC1(O)C(O)=O
InChI Identifier
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)
InChI KeyWHKYNCPIXMNTRQ-UHFFFAOYSA-N