mercaptopurine   Click here for help

GtoPdb Ligand ID: 7226

Synonyms: 6-mercaptopurine | Purinethol® | Xaluprine®
Approved drug PDB Ligand
mercaptopurine is an approved drug (FDA (1953), EMA (2012))
Compound class: Synthetic organic
Comment: Mercaptopurine has immunosuppressive action as well as antineoplastic activity.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 93.26
Molecular weight 152.02
XLogP 0.22
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Sc1ncnc2c1nc[nH]2
Isomeric SMILES Sc1ncnc2c1nc[nH]2
InChI InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI Key GLVAUDGFNGKCSF-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1953)  |  EMA (2012)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug azathioprine
IUPAC Name Click here for help
9H-purine-6-thiol
International Nonproprietary Names Click here for help
INN number INN
587 mercaptopurine
Synonyms Click here for help
6-mercaptopurine | Purinethol® | Xaluprine®
Database Links Click here for help
CAS Registry No. 50-44-2
ChEMBL Ligand CHEMBL1425
DrugBank Ligand DB01033
DrugCentral Ligand 1708
GtoPdb PubChem SID 178103800
PubChem CID 667490
RCSB PDB Ligand PM6
Search Google for chemical match using the InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone GLVAUDGFNGKCSF
Search PubMed clinical trials mercaptopurine
Search PubMed titles mercaptopurine
Search PubMed titles/abstracts mercaptopurine
UniChem Compound Search for chemical match using the InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GLVAUDGFNGKCSF-UHFFFAOYSA-N
Wikipedia Mercaptopurine

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MedChemExpress
6-Mercaptopurine (links to external site)
Cat. No. HY-13677