CHEBI:9555 - tioguanine

ChEBI IDCHEBI:9555
ChEBI Nametioguanine
Stars
DefinitionA 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.
Last Modified23 April 2020
DownloadsMolfile
FormulaC5H5N5S
Net Charge0
Average Mass167.197
Monoisotopic Mass167.02657
SMILESNc1nc(=S)c2ncnc2n1
InChIInChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChIKeyWYWHKKSPHMUBEB-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
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:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
tioguanine (CHEBI:9555) has role anticoronaviral agent (CHEBI:149553)
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)
Incoming Relation(s)
6-methylthioguanine (CHEBI:140528) has functional parent tioguanine (CHEBI:9555)
IUPAC Name 
2-amino-1,9-dihydro-6H-purine-6-thione
INNs  Source
tioguanineKEGG DRUG
tioguaninumChemIDplus
tioguaninaChemIDplus
tioguanineWHO MedNet
Synonyms  Source
ThioguanineKEGG COMPOUND
2-amino-1,9-dihydropurine-6-thionePDBeChem
2-Aminopurine-6-thiolDrugBank
2-Aminopurin-6-thiolDrugBank
2-Amino-6-purinethiolDrugBank
6-MercaptoguanineDrugBank
UniProt Name  Source
6-thioguanineUniProt
Manual XrefsDatabases
C07648KEGG COMPOUND
DX4PDBeChem
D08603KEGG DRUG
DB00352DrugBank
CPD-5721MetaCyc
ThioguanineWikipedia
C00018807KNApSAcK
LSM-6723LINCS
2632DrugCentral
Registry NumbersSources
Reaxys:1074099Reaxys
CAS:154-42-7KEGG COMPOUND
CAS:154-42-7ChemIDplus
Citations