CHEBI:9555 - tioguanine

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ChEBI Name tioguanine
ChEBI ID CHEBI:9555
Definition A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H5N5S
Net Charge 0
Average Mass 167.19200
Monoisotopic Mass 167.027
InChI InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChIKey WYWHKKSPHMUBEB-UHFFFAOYSA-N
SMILES Nc1nc2[nH]cnc2c(=S)[nH]1
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.
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ChEBI Ontology
Outgoing tioguanine (CHEBI:9555) has role antimetabolite (CHEBI:35221)
tioguanine (CHEBI:9555) has role antineoplastic agent (CHEBI:35610)
tioguanine (CHEBI:9555) is a 2-aminopurines (CHEBI:20702)
IUPAC Name
2-amino-1,9-dihydro-6H-purine-6-thione
INNs Sources
tioguanina ChemIDplus
tioguanine KEGG DRUG
tioguanine WHO MedNet
tioguaninum ChemIDplus
Synonyms Sources
2-Amino 6MP ChemIDplus
2-Amino-1,7-dihydro-6H-purine-6-thione ChemIDplus
2-amino-1,9-dihydropurine-6-thione PDBeChem
2-Amino-6-mercaptopurine DrugBank
2-Amino-6-merkaptopurin DrugBank
2-Amino-6-purinethiol DrugBank
2-Aminopurin-6-thiol DrugBank
2-Aminopurine-6(1H)-thione DrugBank
2-Aminopurine-6-thiol DrugBank
6-Mercapto-2-aminopurine DrugBank
6-Mercaptoguanine DrugBank
6-TG ChemIDplus
6-Thioguanine DrugBank
6-thioguanine UniProt
TG DrugBank
ThG DrugBank
Thioguanine KEGG COMPOUND
Tioguanin ChemIDplus
Manual Xrefs Databases
2632 DrugCentral
C00018807 KNApSAcK
C07648 KEGG COMPOUND
CPD-5721 MetaCyc
D08603 KEGG DRUG
DB00352 DrugBank
DX4 PDBeChem
LSM-6723 LINCS
Thioguanine Wikipedia
View more database links
Registry Numbers Types Sources
1074099 Reaxys Registry Number Reaxys
154-42-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
06 April 2018