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.
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 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
Click here for help
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)
1. Wang M, Cao R, Zhang L, Yang X, Liu J, Xu M, Shi Z, Hu Z, Zhong W, Xiao G. (2020)
Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitro.
Cell Res, 30 (3): 269-271. [PMID:32020029]
2. Zhang C-H, Spasov KA, Reilly RA, Hollander K, Stone EA, Ippolito JA, Liosi M-A, Deshmukh MG, Tirado-Rives J, Zhang S et al.. (2021)
Optimization of Triarylpyridinone Inhibitors of the Main Protease of SARS-CoV-2 to Low-Nanomolar Antiviral Potency.
ACS Medicinal Chemistry Letters, [Epub ahead of print]. DOI: 10.1021/acsmedchemlett.1c00326