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Record Information
Version4.0
Creation Date2013-07-04 18:59:43 UTC
Update Date2017-09-27 08:43:54 UTC
HMDB IDHMDB0060792
Secondary Accession Numbers
  • HMDB60792
Metabolite Identification
Common Name6-Thioxanthylic acid
Description6-Thioxanthylic 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
SynonymsNot Available
Chemical FormulaC10H13N4O8PS
Average Molecular Weight380.271
Monoisotopic Molecular Weight380.019170614
IUPAC Name{[(2S,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanyl-9H-purin-9-yl)oxolan-2-yl](hydroxy)methyl}phosphonic acid
Traditional Name[(2S,5R)-3,4-dihydroxy-5-(2-hydroxy-6-sulfanylpurin-9-yl)oxolan-2-yl](hydroxy)methylphosphonic acid
CAS Registry NumberNot Available
SMILES
OC([C@H]1O[C@H](C(O)C1O)N1C=NC2=C1N=C(O)N=C2S)P(O)(O)=O
InChI Identifier
InChI=1S/C10H13N4O8PS/c15-3-4(16)8(22-5(3)9(17)23(19,20)21)14-1-11-2-6(14)12-10(18)13-7(2)24/h1,3-5,8-9,15-17H,(H2,19,20,21)(H2,12,13,18,24)/t3?,4?,5-,8+,9?/m0/s1
InChI KeyGRTRLPZIJODDLV-BQGLTYQTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-thiopurine
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Organophosphonic acid
  • Organophosphonic acid derivative
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Arylthiol
  • Oxacycle
  • Azacycle
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organophosphorus compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility3.23 g/LALOGPS
logP-0.91ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area191.28 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.84 m³·mol⁻¹ChemAxon
Polarizability31.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00771
      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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available