neratinib   Click here for help

GtoPdb Ligand ID: 5686

Synonyms: HKI 272 | HKI-272 | Nerlynx®
Approved drug
neratinib is an approved drug (FDA (2017), EMA (2018))
Compound class: Synthetic organic
Comment: Neratinib is an irreversible inhibitor of the receptor tyrosine kinase (RTK), ErbB2 [4]. It also inhibits the related RTK, EGFR.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 112.4
Molecular weight 556.2
XLogP 3.87
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CCOc1cc2ncc(c(c2cc1NC(=O)C=CCN(C)C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
Isomeric SMILES CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/CN(C)C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
InChI InChI=1S/C30H29ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-12,14-16,18H,4,13,19H2,1-3H3,(H,34,35)(H,36,38)/b9-7+
InChI Key JWNPDZNEKVCWMY-VQHVLOKHSA-N
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
erb-b2 receptor tyrosine kinase 2 Primary target of this compound Hs Inhibitor Inhibition 8.2 pKd - 1
pKd 8.2 (Kd 6x10-9 M) [1]
erb-b2 receptor tyrosine kinase 2 Primary target of this compound Hs Inhibitor Inhibition 7.2 pIC50 - 4
pIC50 7.2 (IC50 5.9x10-8 M) [4]
Description: Inhibition of autophosphorylation of the cytoplasmic domain of the RTK in a cell free system.
epidermal growth factor receptor Hs Inhibitor Inhibition 7.0 pIC50 - 4
pIC50 7.0 (IC50 9.2x10-8 M) [4]
Description: Inhibition of autophosphorylation of the cytoplasmic domain of the RTK in a cell free system.