compound 19 [PMID: 33786375]   Click here for help

GtoPdb Ligand ID: 11615

Compound class: Synthetic organic
Comment: Compound 19 is one of two potential lead SARS-CoV-2 antivirals from the same discovery effort [2]. Both compounds inhibit SARS-CoV-2 3CL protease (Mpro). Compound 21 [PMID: 34408808] is the other lead.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 98.46
Molecular weight 564.08
XLogP 7.01
No. Lipinski's rules broken 1
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Canonical SMILES Clc1cc(cc(c1F)OCc1ccccc1Cl)c1cc(cn(c1=O)c1cccnc1)c1cn(C)c(=O)[nH]c1=O
Isomeric SMILES Clc1cc(cc(c1F)OCc1ccccc1Cl)c1cc(cn(c1=O)c1cccnc1)c1cn(C)c(=O)[nH]c1=O
InChI InChI=1S/C28H19Cl2FN4O4/c1-34-14-21(26(36)33-28(34)38)18-9-20(27(37)35(13-18)19-6-4-8-32-12-19)17-10-23(30)25(31)24(11-17)39-15-16-5-2-3-7-22(16)29/h2-14H,15H2,1H3,(H,33,36,38)
Bioactivity Comments
Compound 19 inhibits SARS-CoV-2 replication with an EC50 of 175 nM, and reduces plaque formation in Vero E6 cells with an EC50 of 80 nM [2]. In Vero E6 infection assays remdesivir's EC50 is reported in the 0.7-2.1 μM range [1]. Compound 19 has favourable aqueous solubility and low cytotoxicity.
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CoV 3C-like (main) protease SARS-CoV-2 Inhibitor Inhibition 7.4 pIC50 - 2
pIC50 7.4 (IC50 4.4x10-8 M) [2]
Description: Inhibition of Mpro proteolytic activity, determined using a substrate peptide cleavage FRET assay.