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
Click here for structure editor
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
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1039-45. [PMID:22037377]
2. Brown GR, Bamford AM, Bowyer J, James DS, Rankine N, Tang E, Torr V, Culbert EJ. (2000)
Naphthyl ketones: a new class of Janus kinase 3 inhibitors.
Bioorg. Med. Chem. Lett., 10 (6): 575-9. [PMID:10741557]
3. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem. J., 451 (2): 313-28. [PMID:23398362]
4. Lai TS, Liu Y, Tucker T, Daniel KR, Sane DC, Toone E, Burke JR, Strittmatter WJ, Greenberg CS. (2008)
Identification of chemical inhibitors to human tissue transglutaminase by screening existing drug libraries.
Chem. Biol., 15 (9): 969-78. [PMID:18804034]
5. Luo C, Laaja P. (2004)
Inhibitors of JAKs/STATs and the kinases: a possible new cluster of drugs.
Drug Discov. Today, 9 (6): 268-75. [PMID:15003245]