tioguanine (CHEBI:9555)

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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

Average Mass

167.19200

Monoisotopic Mass

167.02657

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. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	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	6-methylthioguanine (CHEBI:140528) has functional parent tioguanine (CHEBI:9555)

IUPAC Name

2-amino-1,9-dihydro-6H-purine-6-thione

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

Last Modified

23 April 2020