envonalkib   Click here for help

GtoPdb Ligand ID: 11874

Synonyms: example 27 [WO2014117718A1] | TQ-B3139
Approved drug
envonalkib is an approved drug
Compound class: Synthetic organic
Comment: Envonalkib is described as a tyrosine kinase inhibitor and antineoplastic in the WHO proposed INN list 126 (Jan 2022). This chemical structure is claimed in patent WO2014117718A1, which suggests that it is an ALK inhibitor [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 85.53
Molecular weight 505.14
XLogP 5.76
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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Canonical SMILES COc1cc(ncc1c1cnc(c(c1)O[C@@H](c1c(Cl)ccc(c1Cl)F)C)N)N1CCNC[C@@H]1C
Isomeric SMILES Clc1c(c(ccc1F)Cl)[C@@H](C)Oc1cc(cnc1N)c1cnc(cc1OC)N1[C@H](CNCC1)C
InChI InChI=1S/C24H26Cl2FN5O2/c1-13-10-29-6-7-32(13)21-9-19(33-3)16(12-30-21)15-8-20(24(28)31-11-15)34-14(2)22-17(25)4-5-18(27)23(22)26/h4-5,8-9,11-14,29H,6-7,10H2,1-3H3,(H2,28,31)/t13-,14+/m0/s1
InChI Key BVGDAZBTIVRTGO-UONOGXRCSA-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/)

Bioactivity Comments
Retains inhibitory activity against ALK with mutations L1196M and G1269S [2]. Low activity vs. CYP3A4 (30 μM). Additional targets include ROS1 and MET kinases.
Selectivity at catalytic receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ALK receptor tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 2
pIC50 8.7 (IC50 1.96x10-9 M) [2]