Chemical substance record

Tioguanine

154-42-7C₅H₅N₅S167.197 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	154-42-7	ChEBI ↗
Molecular formula	C₅H₅N₅S	ChEBI ↗
Molar mass	167.197 g/mol	ChEBI ↗
Monoisotopic mass	167.02657 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:9555	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	167.19 g/mol	PubChem ↗
Exact mass	167.02656635 Da	PubChem ↗
Computed XLogP	-0.1	PubChem ↗
Topological polar surface area (Å²)	111	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	2	PubChem ↗
Rotatable bonds	0	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

tioguanine

IUPAC name

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

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)

Names & synonyms

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

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

2-aminopurinesChEBI parent class · 20702 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

anticoronaviral agentantimetaboliteantineoplastic agentanti-anaemic agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00598097 mol

Uses 167.197 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

N

Nitrogen · 5 atoms

41.89%

C

Carbon · 5 atoms

35.92%

S

Sulfur · 1 atom

19.18%

H

Hydrogen · 5 atoms

3.01%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Oral azathioprine leads to higher incorporation of 6-thioguanine in DNA of skin than liver: the protective role of the Keap1/Nrf2/ARE pathway. ↗Cancer prevention research (Philadelphia, Pa.) · 2011 Oct · PMID 21803983

Liquid chromatography-tandem mass spectrometry quantification of 6-thioguanine in DNA using endogenous guanine as internal standard. ↗Journal of chromatography. B, Analytical technologies in the biomedical and life sciences · 2012 Jan 15 · PMID 22178190

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:9555

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 2723601 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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