example 2 [WO2005113580A1]   Click here for help

GtoPdb Ligand ID: 11106

PDB Ligand
Compound class: Synthetic organic
Comment: Example 2 is a covalent inhibitor of the 3CL protease (Mpro) of the SARS-CoV-1 coronavirus [1]. The compound has been shown in complex with SARS-CoV-2 Mpro (see RCSB Protein Database entry 6XHM).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 6
Rotatable bonds 13
Topological polar surface area 152.78
Molecular weight 474.25
XLogP 1
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]([C@@H](NC(=O)[C@@H](NC(=O)c1[nH]c2c(c1)c(OC)ccc2)CC(C)C)C[C@@H]1CCNC1=O)O
Isomeric SMILES OC[C@H]([C@@H](NC(=O)[C@@H](NC(=O)c1[nH]c2c(c1)c(OC)ccc2)CC(C)C)C[C@@H]1CCNC1=O)O
InChI InChI=1S/C24H34N4O6/c1-13(2)9-18(23(32)27-17(20(30)12-29)10-14-7-8-25-22(14)31)28-24(33)19-11-15-16(26-19)5-4-6-21(15)34-3/h4-6,11,13-14,17-18,20,26,29-30H,7-10,12H2,1-3H3,(H,25,31)(H,27,32)(H,28,33)/t14-,17-,18-,20+/m0/s1
InChI Key FDQSUXUTXIGUIA-PRIDNEQBSA-N
Bioactivity Comments
Example 2 inhibits 3CL protease (Mpro) of the SARS-CoV-1 coronavirus with an IC50 of 4 nM (in a FRET assay measuring protease catalysed cleavage of a TAMRA-labelled substrate peptide) and has in vitro antiviral activity [1].