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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:46 UTC
Update Date2019-07-23 07:14:17 UTC
HMDB IDHMDB0060412
Secondary Accession Numbers
  • HMDB60412
Metabolite Identification
Common Name6-Methylmercaptopurine
Description6-Methylmercaptopurine, also known as thiopurine S-methylether, belongs to the class of organic compounds known as 6-thiopurines. 6-thiopurines 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. It is a thiopurine. 6-Methylmercaptopurine is a metabolite of mercaptopurine. 6-Methylmercaptopurine is a strong basic compound (based on its pKa). Mercaptopurine (also called 6-mercaptopurine, 6-MP or its brand name Purinethol) is an immunosuppressive drug. 6-Methylmercaptopurine exists in all living organisms, ranging from bacteria to humans. S-adenosylhomocysteine and 6-methylmercaptopurine can be biosynthesized from mercaptopurine and S-adenosylmethionine through the action of the enzyme thiopurine S-methyltransferase. In humans, 6-methylmercaptopurine is involved in mercaptopurine metabolism pathway.
Structure
Data?1563866057
Synonyms
ValueSource
Thiopurine S-methyletherChEBI
MethylmercaptopurineHMDB
6-MethylmercaptopurineChEBI
6-MethylthiopurineMeSH
Chemical FormulaC6H6N4S
Average Molecular Weight166.204
Monoisotopic Molecular Weight166.031316902
IUPAC Name6-(methylsulfanyl)-9H-purine
Traditional Name6-methylthiopurine
CAS Registry NumberNot Available
SMILES
CSC1=NC=NC2=C1N=CN2
InChI Identifier
InChI=1S/C6H6N4S/c1-11-6-4-5(8-2-7-4)9-3-10-6/h2-3H,1H3,(H,7,8,9,10)
InChI KeyUIJIQXGRFSPYQW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-thiopurines. 6-thiopurines 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-thiopurines
Alternative Parents
Substituents
  • 6-thiopurine
  • Aryl thioether
  • Alkylarylthioether
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility3.6 g/LALOGPS
logP0.64ALOGPS
logP0.93ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)4.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.66 m³·mol⁻¹ChemAxon
Polarizability16 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-3900000000-5450fbc7c306ca432d9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c4246e06dc5bb517b84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-34b7aa251463372ebb71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-d5deee2755af859be56cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-0ea1841b20f3a789060bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-0d48b186067b926b80ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-8e795930466ee68a8a80Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16614
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound5778
      PDB IDXQG
      ChEBI ID28279
      Food Biomarker OntologyNot Available
      VMH IDM01166
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Involved in thiopurine S-methyltransferase activity
      Specific function:
      Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
      Gene Name:
      TPMT
      Uniprot ID:
      P51580
      Molecular weight:
      28180.09
      Reactions
      Mercaptopurine + S-Adenosylmethionine → 6-Methylmercaptopurine + S-Adenosylhomocysteinedetails
      General function:
      Involved in hypoxanthine phosphoribosyltransferase activity
      Specific function:
      Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
      Gene Name:
      HPRT1
      Uniprot ID:
      P00492
      Molecular weight:
      24579.155
      Reactions
      6-Methylmercaptopurine + Phosphoribosyl pyrophosphate → 6-Methylthiopurine 5'-monophosphate ribonucleotide + Pyrophosphatedetails