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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:46 UTC
Update Date2023-02-21 17:29:58 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
Thumb
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available128.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00002135
[M+H]+Not Available130.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00002135
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
MarkerDB IDNot Available
Good Scents IDNot Available
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