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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2023-02-21 17:29:11 UTC
HMDB IDHMDB0059663
Secondary Accession Numbers
  • HMDB59663
Metabolite Identification
Common Name2-Oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline
Description2-Oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (CAS: 255828-59-2), also known as OHCU, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Outside of the human body, 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline has been detected, but not quantified, in soybeans. This could make 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline a potential biomarker for the consumption of these foods. 2-Oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline is part of the purine metabolism pathway. It is a substrate for putative 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline decarboxylase.
Structure
Thumb
Synonyms
ValueSource
(5S)-2,5-Dihydroxy-4-[(C-hydroxycarbonimidoyl)imino]-4,5-dihydro-1H-imidazole-5-carboxylateHMDB
(4S)-5-(Carbamoylimino)-4-hydroxy-2-oxoimidazolidine-4-carboxylic acidHMDB
(5S)-4-[(Aminocarbonyl)amino]-2,5-dihydro-5-hydroxy-2-oxo-1H-imidazole-5-carboxylic acidHMDB
(S)-2-oxo-4-Hydroxy-4-carboxy-5-ureidoimidazolineHMDB
(S)-5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H imidazole-5-carboxylateHMDB
(S)-OHCUHMDB
2-oxo-4-Hydroxy-4-carboxy-5-ureidoimidazoleHMDB
4-(Carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylateHMDB
4-[(Aminocarbonyl)amino]-2,5-dihydro-5-hydroxy-2-oxo-1H-imidazole-5-carboxylic acidHMDB
5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylateHMDB
OHCUHMDB
2-Oxo-4-hydroxy-4-carboxy-5-ureidoimidazolineHMDB
Chemical FormulaC5H6N4O5
Average Molecular Weight202.126
Monoisotopic Molecular Weight202.033819309
IUPAC Name(5S)-4-(carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid
Traditional Name(4S)-5-(carbamoylamino)-4-hydroxy-2-oxo-3H-imidazole-4-carboxylic acid
CAS Registry Number1320343-65-4
SMILES
NC(=O)NC1=NC(=O)N[C@@]1(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)/t5-/m0/s1
InChI KeyWHKYNCPIXMNTRQ-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy acid
  • 3-imidazoline
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amidine
  • Amidine
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001617
KNApSAcK IDC00007532
Chemspider ID61493300
KEGG Compound IDC12248
BioCyc IDCPD-5821
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101957722
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Not Available
Specific function:
Catalyzes the stereoselective decarboxylation of 2-oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline (OHCU) to (S)-allantoin (Potential).
Gene Name:
PRHOXNB
Uniprot ID:
A6NGE7
Molecular weight:
19129.52
Reactions
2-Oxo-4-hydroxy-4-carboxy-5-ureidoimidazoline → Allantoin + CO(2)details