5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate (ECMDB23108) (M2MDB003498)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (204)
Record Information
Version2.0
Creation Date2012-10-10 12:16:59 -0600
Update Date2015-06-03 17:25:56 -0600
Secondary Accession Numbers
  • ECMDB23108
Identification
Name:5-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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • 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
Chemical Formula:C5H6N4O5
Weight:Average: 202.1249
Monoisotopic: 202.033819322
InChI Key:WHKYNCPIXMNTRQ-UHFFFAOYSA-N
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)
CAS number:Not Available
IUPAC Name:4-(carbamoylamino)-5-hydroxy-2-oxo-2,5-dihydro-1H-imidazole-5-carboxylic acid
Traditional IUPAC Name:5-(carbamoylamino)-4-hydroxy-2-oxo-3H-imidazole-4-carboxylic acid
SMILES:NC(=O)NC1=NC(=O)NC1(O)C(O)=O
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
  • Alpha-hydroxy acid
  • Hydroxy acid
  • 3-imidazoline
  • Carbonic acid derivative
  • Urea
  • Alkanolamine
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.85 g/LALOGPS
logP-1.9ALOGPS
logP-2.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area154.11 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.67 m³·mol⁻¹ChemAxon
Polarizability16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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
5-Hydroxyisourate + Water > 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fu-6900000000-d10ae3e6c0ec2b2ce715View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3091000000-2d5a8154318d1c851aebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ik9-1930000000-aa0ce54956d155b53ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-4b7e4cde80ee20857785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-b47e099fd673e89bef01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-1900000000-ada3c5b0af634149d258View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vi-7900000000-8cfac7d8a2916a662122View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-87b0901f8a0972ac01f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0290000000-6aef2ea3d16e64f66e0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gw3-0920000000-77d0905884a3fca8fd7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-11c7af77cb066557a541View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0690000000-81226e034d27b996a665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-3900000000-6c8214de7999a22c4230View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-04fd0d084ea29b98bee7View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID31132
HMDB IDHMDB0301917
Pubchem Compound ID443736
Kegg IDC12248
ChemSpider ID391844
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Hydroxyisourate hydrolase
General function:
Not Available
Specific function:
Not Available
Gene Name:
hiuH
Uniprot ID:
P76341
Molecular weight:
Not Available