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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).

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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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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 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

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 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+
InChI Key MRFOPLWJZULAQD-SWGQDTFXSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(E)-3-(6-aminopyridin-3-yl)-N-[[5-[4-(4,4-difluoropiperidine-1-carbonyl)phenyl]-7-(4-fluorophenyl)-1-benzofuran-2-yl]methyl]prop-2-enamide
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
Search Google for chemical match using the InChIKey MRFOPLWJZULAQD-SWGQDTFXSA-N
Search Google for chemicals with the same backbone MRFOPLWJZULAQD
Search PubMed clinical trials padnarsertib
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Search PubMed titles/abstracts padnarsertib
UniChem Compound Search for chemical match using the InChIKey MRFOPLWJZULAQD-SWGQDTFXSA-N
UniChem Connectivity Search for chemical match using the InChIKey MRFOPLWJZULAQD-SWGQDTFXSA-N

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Padnarsertib (links to external site)
Cat. No. HY-12793