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Record Information
Version4.0
Creation Date2013-07-04 18:59:31 UTC
Update Date2017-09-27 08:43:54 UTC
HMDB IDHMDB0060789
Secondary Accession Numbers
  • HMDB60789
Metabolite Identification
Common Name6-Thioguanylic acid
Description6-Thioguanylic 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-TG NucleotideMeSH
6-Thioguanine nucleotideMeSH
6-Thioguanosine-5'-phosphateMeSH
Chemical FormulaC10H14N5O7PS
Average Molecular Weight379.286
Monoisotopic Molecular Weight379.035155029
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=S)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C10H14N5O7PS/c11-10-13-7-4(8(24)14-10)12-2-15(7)9-6(17)5(16)3(22-9)1-21-23(18,19)20/h2-3,5-6,9,16-17H,1H2,(H2,18,19,20)(H3,11,13,14,24)/t3-,5-,6-,9-/m1/s1
InChI KeyBPZXYEUJBFHASJ-UUOKFMHZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purinethione
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidinethione
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur 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 Solubility2.07 g/LALOGPS
logP-1.4ALOGPS
logP-3.6ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)3.39ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area184.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.05 m³·mol⁻¹ChemAxon
Polarizability33.25 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-014i-0913000000-96a4f72bf492be7f7409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-dfebaa4c8fd99d57db92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1900000000-f58433842072d381834eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-6519000000-238224e8d8f10e7d2ce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-9700000000-001e7924823178c2fa60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-37c3f1a5f378f4931d75View 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 Metabolism PathwayPw000623Pw000623 greyscalePw000623 simpleNot Available
Thioguanine PathwayPw000429Pw000429 greyscalePw000429 simpleNot Available
Displaying all 5 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 IDDBMET00768
      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