tioguanine

CHEBI:9555 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:20702 CHEBI:20702

Chemical structure

Computed structure properties
Molecular formula	C5H5N5S
Charge	0
Average mass	167.197 Da
Monoisotopic mass	167.02657 Da
Source	ChEBI
InChIKey	WYWHKKSPHMUBEB-UHFFFAOYSA-N

SMILES

Nc1nc(=S)c2ncnc2n1

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)

Also called

tioguanina (INN)— chebi
tioguaninum (INN)— chebi
2-amino-1,9-dihydro-6H-purine-6-thione (EXACT_SYNONYM)— chebi
2-Amino 6MP (EXACT_SYNONYM)— chebi
2-Amino-1,7-dihydro-6H-purine-6-thione (EXACT_SYNONYM)— chebi
2-Amino-6-mercaptopurine (EXACT_SYNONYM)— chebi
2-Amino-6-merkaptopurin (EXACT_SYNONYM)— chebi
2-Amino-6-purinethiol (EXACT_SYNONYM)— chebi
2-Aminopurin-6-thiol (EXACT_SYNONYM)— chebi
2-Aminopurine-6(1H)-thione (EXACT_SYNONYM)— chebi
2-Aminopurine-6-thiol (EXACT_SYNONYM)— chebi
2-amino-1,9-dihydropurine-6-thione (EXACT_SYNONYM)— chebi
6-Mercapto-2-aminopurine (EXACT_SYNONYM)— chebi
6-Mercaptoguanine (EXACT_SYNONYM)— chebi
6-TG (EXACT_SYNONYM)— chebi
6-Thioguanine (EXACT_SYNONYM)— chebi
TG (EXACT_SYNONYM)— chebi
ThG (EXACT_SYNONYM)— chebi
Thioguanine (EXACT_SYNONYM)— chebi
Tioguanin (EXACT_SYNONYM)— chebi
6-thioguanine (RELATED_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:154-42-7
drugbank:DB00352
drugcentral:2632
kegg.compound:C07648
kegg.drug:D08603
knapsack:C00018807
lincs.smallmolecule:LSM-6723
metacyc.compound:CPD-5721
pdb-ccd:DX4
reaxys:1074099
wikipedia.en:Thioguanine

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:149553 CHEBI:149553

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:9555`	tioguanine	`antibioticmech:chebi-39c1d436bc`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.