JAK3 inhibitor IV   

GtoPdb Ligand ID: 5994

Synonyms: ZM-39923 | ZM39923
Compound class: Synthetic organic
Comment: This is compound 7 in [2], and is also known as ZM39923. It was originally identified as an ATP-binding site inhibitor of JAK3 [5], but has additionally been reported to inhibit transglutaminase 2 (TGM2) with nanomolar potency in vitro [4].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 20.31
Molecular weight 331.19
XLogP 5.44
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CC(N(Cc1ccccc1)CCC(=O)c1ccc2c(c1)cccc2)C
Isomeric SMILES CC(N(Cc1ccccc1)CCC(=O)c1ccc2c(c1)cccc2)C
InChI InChI=1S/C23H25NO/c1-18(2)24(17-19-8-4-3-5-9-19)15-14-23(25)22-13-12-20-10-6-7-11-21(20)16-22/h3-13,16,18H,14-15,17H2,1-2H3
InChI Key JSASWRWALCMOQP-UHFFFAOYSA-N
Bioactivity Comments
The potency of ZM39923 as a TGM2 inhibitor is significantly increased by the removal of DTT from the enzyme activity assay (IC50 at 10 mM DTT is 3 μM, compared to 10 nM without DTT) [4].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
transglutaminase 2 Hs Inhibitor Inhibition 8.0 pIC50 - 4
pIC50 8.0 (IC50 1x10-8 M) [4]
Description: In the absence of DTT.
Janus kinase 3 Hs Inhibitor Inhibition 7.1 pIC50 - 2
pIC50 7.1 (IC50 7.9x10-8 M) [2]
Janus kinase 1 Hs Inhibitor Inhibition 4.4 pIC50 - 2
pIC50 4.4 (IC50 3.981x10-5 M) [2]