You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:45 UTC
Update Date2020-06-15 17:04:53 UTC
HMDB IDHMDB0030097
Secondary Accession Numbers
  • HMDB30097
Metabolite Identification
Common Name5-Hydroxyisourate
Description5-Hydroxyisourate (CAS: 6960-30-1) belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. 5-Hydroxyisourate is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyisourate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 5-hydroxyisourate has been detected, but not quantified in, several different foods, such as soybeans, common thymes, poppies, blackcurrants, black elderberries, and rapes. This could make 5-hydroxyisourate a potential biomarker for the consumption of these foods. 5-Hydroxyisourate is the product of the oxidation of uric acid by urate oxidase.
Structure
Data?1583778041
Synonyms
ValueSource
(S)-5-Hydroxyisouric acidGenerator
5,7-Dihydro-5-hydroxy-1H-purine-2,6,8(3H)-trioneHMDB
5-HydroxyisourateHMDB
5H-Purine-2,5,6,8-tetrolHMDB
Chemical FormulaC5H4N4O4
Average Molecular Weight184.111
Monoisotopic Molecular Weight184.023254625
IUPAC Name(5S)-5-hydroxy-2,5,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name(5S)-5-hydroxy-7,9-dihydro-1H-purine-2,6,8-trione
CAS Registry Number151359-24-9
SMILES
O[C@@]12NC(=O)NC1=NC(=O)NC2=O
InChI Identifier
InChI=1S/C5H4N4O4/c10-2-5(13)1(6-3(11)8-2)7-4(12)9-5/h13H,(H3,6,7,8,9,10,11,12)/t5-/m0/s1
InChI KeyLTQYPAVLAYVKTK-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Purinone
  • Alpha-amino acid or derivatives
  • Alkaloid or derivatives
  • Ureide
  • Pyrimidone
  • N-acyl urea
  • Pyrimidine
  • 1,3-diazinane
  • 3-imidazoline
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP-1.5ALOGPS
logP-2.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.59 m³·mol⁻¹ChemAxon
Polarizability14.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB001616
KNApSAcK IDC00007531
Chemspider IDNot Available
KEGG Compound IDC11821
BioCyc ID5-HYDROXYISOURATE
BiGG IDNot Available
Wikipedia Link5-Hydroxyisourate
METLIN IDNot Available
PubChem Compound101957720
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDC11821
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .