azathioprine

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azathioprine

Ligand id: 7120

Name: azathioprine

View more information in the IUPHAR Pharmacology Education Project: azathioprine

Structure and Physico-chemical Properties

2D Structure

Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

View interactive charts of activity data from GtoPdb and ChEMBL (where available) across species

Bioactivity Comments
Azathioprine is reported to inhibit peptidylarginine deiminase 4 (PADI4), albeit with very low in vitro affinity [2]. PADI enzymes catalyze the hydrolytic deimination of protein arginine to produce protein citrulline and ammonia [1] and cause chromatin decondensation. Dysregulated PADI4 activity may be involved in cancer progression as it is overexpressed in many malignant tumours, where enhanced chromatin decondensation is involved in promoting pluripotency and stem cell maintenance.

Bioactivity Comments

Azathioprine is reported to inhibit peptidylarginine deiminase 4 (PADI4), albeit with very low in vitro affinity [2]. PADI enzymes catalyze the hydrolytic deimination of protein arginine to produce protein citrulline and ammonia [1] and cause chromatin decondensation. Dysregulated PADI4 activity may be involved in cancer progression as it is overexpressed in many malignant tumours, where enhanced chromatin decondensation is involved in promoting pluripotency and stem cell maintenance.