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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:00:33 UTC
Update Date2017-12-07 18:04:34 UTC
HMDB IDHMDB0060804
Secondary Accession Numbers
  • HMDB60804
Metabolite Identification
Common Name8-Hydroxythioguanine
Description8-Hydroxythioguanine 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
SynonymsNot Available
Chemical FormulaC5H5N5OS
Average Molecular Weight183.191
Monoisotopic Molecular Weight183.021480497
IUPAC Name2-imino-6-sulfanyl-3,9-dihydro-2H-purin-8-ol
Traditional Name2-imino-6-sulfanyl-3,9-dihydropurin-8-ol
CAS Registry Number88550-56-5
SMILES
OC1=NC2=C(N1)NC(=N)N=C2S
InChI Identifier
InChI=1S/C5H5N5OS/c6-4-8-2-1(3(12)10-4)7-5(11)9-2/h(H5,6,7,8,9,10,11,12)
InChI KeyTWLCFFLQLXBKAP-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
  • Aminopyrimidine
  • Pyrimidinethione
  • Primary aromatic amine
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.38 g/LALOGPS
logP0.67ALOGPS
logP0.44ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)6.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area97.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.19 m³·mol⁻¹ChemAxon
Polarizability16.73 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, Positivesplash10-001j-5900000000-56d5db075aa7e569e7caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ec-5940000000-54b4f91f79057b84c61fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-9706f696d6be973441f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f8af21c55bc43a6891f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9500000000-e33e6883a1ccca72cffaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-d6e57593898e001d104fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2900000000-7eff9d90995adaa784fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9300000000-8d7f3c7fb4dc6c5d0fd4View 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
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 IDDBMET00780
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound10442362
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available