Compound
6-thioguanine
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.
Definition from ChEBI (CHEBI:9555), read 2026-09-23. CC BY 4.0.
Structure
- Class
- Organic compound
- Formula
- C5H5N5S
- Mass
- 167.197 g/mol
- Charge
- 0
- InChIKey
- WYWHKKSPHMUBEB-UHFFFAOYSA-N
- SMILES
- Nc1nc(=S)c2ncnc2n1
- Look it up
- ChEBIBy InChIKey
Identity from ChEBI. Not evidence.
What it touches on the way
Mechanistic reach
1 entity
1 entities reached.
0 reported hops1 assembled from the scaffold
What the reference databases state
Regulatory determinations
LiverTox likelihood score ALiverTox
LiverTox Likelihood Score A — well known, well described and well reported to cause liver injury. Chapter: "Thioguanine". Source: LiverTox Master List (NBK571102).
The document·Public Domain (NLM/NIH)·Transcribed, not assessed
Chemical structure
- 6-methylthioguanine has the functional parent 6-thioguanineCompoundChEBI CHEBI:140528Inferred only
Statements
3 statements
3 statements · 1 reference database · Subject: 6-thioguanine · Sources: Rhea
- 6-thioguanine is converted to 6-methylthioguanineCompoundRhea RHEA:56580Inferred only
- 6-methylthioguanine is converted to 6-thioguanineCompoundRhea RHEA:56580Inferred only
- 6-thioguanine is metabolised by TPMTProteinRhea RHEA:56580Inferred only
Reactions
1 reaction
6-thioguanine+S-adenosyl-L-methionine6-methylthioguanine+S-adenosyl-L-homocysteine+hydron
Catalysed by TPMT
Reaction pageDirection not assertedBalanced
Rhea RHEA:56580CC BY 4.0Reference data
Other names
18 names
Resolves to: 6-thioguanine
- Also called
- 2-Amino 6MP2-Amino-1,7-dihydro-6H-purine-6-thione2-amino-1,9-dihydropurine-6-thione2-Amino-6-mercaptopurine2-Amino-6-merkaptopurin2-Amino-6-purinethiol2-Aminopurin-6-thiol2-Aminopurine-6-thiol2-Aminopurine-6(1H)-thione6-Mercapto-2-aminopurine6-Mercaptoguanine6-TGTGThGThioguanineTioguanintioguanine
- Systematic name
- 2-amino-1,9-dihydro-6H-purine-6-thione