Record Information
Version2.0
Creation Date2012-10-10 12:17:04 -0600
Update Date2015-06-03 17:25:57 -0600
Secondary Accession Numbers
  • ECMDB23110
Identification
Name:5-Hydroxyisourate
Description5-Hydroxyisourate is involved in purine degradation. It is a substrate of 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.
Structure
Thumb
Synonyms:
  • 5-Hydroxy-2,6-dioxo-2,5,6,7-tetrahydro-1H-purin-8-olate
  • 5-Hydroxy-2,6-dioxo-2,5,6,7-tetrahydro-1H-purin-8-olic acid
  • 5-hydroxy-3,7-dihydropurine-2,6,8-trione
  • 5-Hydroxy-5,7-dihydro-1H-purin-2,6,8(3H)-trion
  • 5-hydroxy-5,7-dihydro-1H-purine-2,6,8(9H)-trione
  • 5-Hydroxyisoate
  • 5-Hydroxyisoic acid
  • 5-Hydroxyisouric acid
Chemical Formula:C5H4N4O4
Weight:Average: 184.1097
Monoisotopic: 184.023254636
InChI Key:LTQYPAVLAYVKTK-UHFFFAOYSA-N
InChI: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)
CAS number:Not Available
IUPAC Name:5-hydroxy-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione
Traditional IUPAC Name:5-hydroxyisourate
SMILES:OC12NC(=O)N=C1NC(=O)NC2=O
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
  • Alpha-amino acid or derivatives
  • Purinone
  • Alkaloid or derivatives
  • N-acyl urea
  • Pyrimidone
  • Ureide
  • 1,3-diazinane
  • Pyrimidine
  • Dicarboximide
  • 3-imidazoline
  • Carbonic acid derivative
  • Urea
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Carboximidamide
  • Azacycle
  • Alkanolamine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP-1.5ALOGPS
logP-2.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.59 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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, Positivesplash10-03di-3900000000-9b1ae81006075657af68View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02p3-9650000000-825c5f18d73a46374e67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-8943d9513d56a0d37995View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-bacca7a51ca984e98e8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-31f89414751f8acd2682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-2900000000-6239a44eb8a55c6e1a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-c4edb92f0fb9241b2770View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90e2feee28cabb16c73cView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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.
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18072
HMDB IDHMDB30097
Pubchem Compound ID250388
Kegg IDC11821
ChemSpider ID219288
Wikipedia5-Hydroxyisourate
BioCyc IDNot Available

Enzymes

General function:
Not Available
Specific function:
Not Available
Gene Name:
hiuH
Uniprot ID:
P76341
Molecular weight:
Not Available