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Record Information
Version4.0
Creation Date2013-06-15 17:46:44 UTC
Update Date2017-09-27 08:43:50 UTC
HMDB IDHMDB0060601
Secondary Accession Numbers
  • HMDB60601
Metabolite Identification
Common Name6-thiouric acid
Description6-thiouric acid is a metabolite of azathioprine. Azathioprine is a purine analogue immunosuppressive drug. It is used to prevent rejection following organ transplantation, and to treat a vast array of autoimmune diseases, including rheumatoid arthritis, pemphigus, inflammatory bowel disease, multiple sclerosis, autoimmune hepatitis, atopic dermatitis, myasthenia gravis, neuromyelitis optica or Devic's disease, restrictive lung disease, and others. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
6-Thiouric acidKegg
6-ThioateGenerator
6-Thioic acidGenerator
Thiouric acidMeSH
Chemical FormulaC5H4N4O2S
Average Molecular Weight184.176
Monoisotopic Molecular Weight184.005496082
IUPAC Name6-sulfanyl-9H-purine-2,8-diol
Traditional Name6-thio- (van) (8CI) uric acid
CAS Registry NumberNot Available
SMILES
OC1=NC2=C(N1)N=C(O)N=C2S
InChI Identifier
InChI=1S/C5H4N4O2S/c10-4-6-1-2(7-4)8-5(11)9-3(1)12/h(H4,6,7,8,9,10,11,12)
InChI KeySXHQUGJSTGOXMD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentPurinones
Alternative Parents
Substituents
  • Purinethione
  • Purinone
  • Pyrimidone
  • Pyrimidinethione
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Thiolactam
  • Urea
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.91 g/LALOGPS
logP0.96ALOGPS
logP1.15ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area94.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.29 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-5ffb057929aea62d8de0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0900000000-f3680c86386020f06164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-d17684ad8a62062d6760View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-9517c279e50325074231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053j-3900000000-83f3851b60664440e383View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9100000000-2a32afac850b7f75b0a9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Azathioprine PathwayPw000266Pw000266 greyscalePw000266 simpleNot Available
Mercaptopurine Metabolism PathwayPw000585Pw000585 greyscalePw000585 simpleNot Available
Mercaptopurine PathwayPw000267Pw000267 greyscalePw000267 simpleNot Available
Thioguanine PathwayPw000429Pw000429 greyscalePw000429 simpleNot Available
Displaying all 4 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET01009
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16613
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound3032417
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available