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Record Information
Version3.6
Creation Date2013-07-04 19:05:07 UTC
Update Date2017-08-18 12:52:08 UTC
HMDB IDHMDB0060876
Secondary Accession Numbers
  • HMDB60876
Metabolite Identification
Common NameThioxanthine monophosphate
DescriptionThioxanthine monophosphate 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 FormulaC5H3N4O5PS
Average Molecular Weight262.14
Monoisotopic Molecular Weight261.956176428
IUPAC Name9-(hydrogen phosphonatooxy)-6-sulfanyl-9H-purin-2-olate
Traditional Name9-(hydrogen phosphonatooxy)-6-sulfanylpurin-2-olate
CAS Registry NumberNot Available
SMILES
OP([O-])(=O)ON1C=NC2=C1N=C([O-])N=C2S
InChI Identifier
InChI=1S/C5H5N4O5PS/c10-5-7-3-2(4(16)8-5)6-1-9(3)14-15(11,12)13/h1H,(H2,11,12,13)(H2,7,8,10,16)/p-2
InChI KeyOAOIXPPCQSJBRI-UHFFFAOYSA-L
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 6-thiopurines. These are compounds containing a purine that carries a thiol group at the 6-position. 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 Parent6-thiopurines
Alternative Parents
Substituents
  • 6-thiopurine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Arylthiol
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility2.64 mg/mLALOGPS
logP0.38ALOGPS
logP-0.33ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area136.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.31 m3·mol-1ChemAxon
Polarizability19.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Azathioprine PathwaySMP00427Not Available
Mercaptopurine Metabolism PathwaySMP00609Not Available
Mercaptopurine PathwaySMP00428Not Available
Thioguanine PathwaySMP00430Not 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 IDDBMET01010
      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
      NuGOwiki LinkHMDB0060876
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available