azathioprine   Click here for help

GtoPdb Ligand ID: 7120

Synonyms: Azasan® | BW-57-322 | Imuran® | Jayempi®
Approved drug Immunopharmacology Ligand
azathioprine is an approved drug (FDA (1968), EMA (2021))
Compound class: Synthetic organic
Comment: Azathioprine is an immunosuppressive antimetabolite. The active drug is believed to be mercaptopurine.
Marketed formulations may contain azathioprine sodium (PubChem CID 23678403).
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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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Click here for structure editor
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 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 143.4
Molecular weight 277.04
XLogP 0.67
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 Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
Isomeric SMILES Cn1cnc(c1Sc1ncnc2c1nc[nH]2)N(=O)=O
InChI InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChI Key LMEKQMALGUDUQG-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/)
References
1. Jones JE, Causey CP, Knuckley B, Slack-Noyes JL, Thompson PR. (2009)
Protein arginine deiminase 4 (PAD4): Current understanding and future therapeutic potential.
Curr Opin Drug Discov Devel, 12 (5): 616-27. [PMID:19736621]
2. Knuckley B, Luo Y, Thompson PR. (2008)
Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors.
Bioorg Med Chem, 16 (2): 739-45. [PMID:17964793]