CHEBI:50667 - mercaptopurine

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ChEBI Name mercaptopurine
ChEBI ID CHEBI:50667
Definition A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C5H4N4S
Net Charge 0
Average Mass 152.17822
Monoisotopic Mass 152.016
InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
SMILES S=c1[nH]cnc2nc[nH]c12
Roles Classification
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mercaptopurine (CHEBI:50667) has role antimetabolite (CHEBI:35221)
mercaptopurine (CHEBI:50667) has role antineoplastic agent (CHEBI:35610)
mercaptopurine (CHEBI:50667) is a purines (CHEBI:26401)
mercaptopurine (CHEBI:50667) is tautomer of purine-6-thiol (CHEBI:2208)
Incoming mercaptopurine hydrate (CHEBI:31822) has part mercaptopurine (CHEBI:50667)
purine-6-thiol (CHEBI:2208) is tautomer of mercaptopurine (CHEBI:50667)
IUPAC Name
1,7-dihydro-6H-purine-6-thione
INNs Sources
Mercaptopurina ChemIDplus
mercaptopurine ChEBI
mercaptopurinum ChemIDplus
Synonyms Sources
6 MP ChemIDplus
6-Mercaptopurine ChemIDplus
6-MP ChemIDplus
6-Thiohypoxanthine ChemIDplus
6-Thioxopurine ChemIDplus
mercaptopurine UniProt
Mercaptopurine KEGG COMPOUND
Mercapurin DrugBank
Brand Names Sources
Puri-Nethol DrugBank
Purinethol DrugBank
Manual Xrefs Databases
C02380 KEGG COMPOUND
D04931 KEGG DRUG
DB01033 DrugBank
PM6 PDBeChem
US2697709 Patent
US2721866 Patent
View more database links
Registry Numbers Types Sources
132916 Beilstein Registry Number Beilstein
132916 Reaxys Registry Number Reaxys
50-44-2 CAS Registry Number KEGG COMPOUND
50-44-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16267626 PubMed citation Europe PMC
28011186 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
28212467 PubMed citation Europe PMC
28295989 PubMed citation Europe PMC
28301625 PubMed citation Europe PMC
28406092 PubMed citation Europe PMC
28418010 PubMed citation Europe PMC
28484608 PubMed citation Europe PMC
28574837 PubMed citation Europe PMC
Last Modified
05 April 2018