padnarsertib   Click here for help

GtoPdb Ligand ID: 10593

Synonyms: KPT-9274 | KPT9274 | PAK4-IN-1
PDB Ligand
Compound class: Synthetic organic
Comment: KPT-9274 is a small molecule that has reported inhibitory activity against PAK4 and NAMPT [3,6]. It is being developed by Karyopharm Therapeutics for anti-cancer efficacy in solid tumours [2,5] and in B cell malignancies [7]. KPT-9274 is suggested to act as an allosteric modulator of PAK4 that does not interfere with the enzyme's kinase activity (in contrast to the type 1 ATP-competitive PAK kinase inhibitor PF-3758309). It produces dose-dependent antitumour effects in solid and haematologic cell lines at low nanomolar concentrations [1]. KPT-9274 is claimed as example 728 in patent WO2015003166A1 [4].
The chemical structure of KPT-9274 is identical to that which was submitted to the WHO for the INN padnarsertib (proposed INN list 126, Jan 2022).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 101.46
Molecular weight 610.22
XLogP 7.1
No. Lipinski's rules broken 1
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Canonical SMILES O=C(NCc1cc2c(o1)c(cc(c2)c1ccc(cc1)C(=O)N1CCC(CC1)(F)F)c1ccc(cc1)F)C=Cc1ccc(nc1)N
Isomeric SMILES O=C(NCc1cc2c(o1)c(cc(c2)c1ccc(cc1)C(=O)N1CCC(CC1)(F)F)c1ccc(cc1)F)/C=C/c1ccc(nc1)N
InChI InChI=1S/C35H29F3N4O3/c36-28-9-7-24(8-10-28)30-19-26(23-3-5-25(6-4-23)34(44)42-15-13-35(37,38)14-16-42)17-27-18-29(45-33(27)30)21-41-32(43)12-2-22-1-11-31(39)40-20-22/h1-12,17-20H,13-16,21H2,(H2,39,40)(H,41,43)/b12-2+
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
11749 padnarsertib
Synonyms Click here for help
KPT-9274 | KPT9274 | PAK4-IN-1
Database Links Click here for help
CAS Registry No. 1643913-93-2 (source: PubChem)
GtoPdb PubChem SID 404859040
PubChem CID 117779453
RCSB PDB Ligand 96Q
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