WU-04   Click here for help

GtoPdb Ligand ID: 12602

Synonyms: WU04
PDB Ligand
Compound class: Synthetic organic
Comment: WU-04 is a noncovalent (reversible) inhibitor of the SARS-CoV-2 main protease (Mpro; 3CLpro) [1]. In vitro nhibition of SARS-CoV and MERS-CoV main proteases is also demonstrated.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 125.73
Molecular weight 526.38
XLogP 3.67
No. Lipinski's rules broken 1
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Canonical SMILES CNC(=O)C1=CC(=CC(=C1N[C@@H]2CCCC[C@@H]2NC(=O)C3=CN=CC4=C3C=CC=C4)[N+](=O)[O-])Br
Isomeric SMILES CNC(=O)C1=C(C(=CC(=C1)Br)[N+](=O)[O-])N[C@@H]2CCCC[C@@H]2NC(=O)C3=CN=CC4=CC=CC=C43
InChI InChI=1S/C24H24BrN5O4/c1-26-23(31)17-10-15(25)11-21(30(33)34)22(17)28-19-8-4-5-9-20(19)29-24(32)18-13-27-12-14-6-2-3-7-16(14)18/h2-3,6-7,10-13,19-20,28H,4-5,8-9H2,1H3,(H,26,31)(H,29,32)/t19-,20+/m1/s1
Bioactivity Comments
The half life of WO-04 is dramaitcally extended (in human liver microsomes) in the presence of ritonavir (which inhibits its metabolism by CYP3A4) [1]. Pharmacokinetics support oral administration, particulary when administered in conjunction with ritonavir.
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 pKd - 1
pKd 7.4 (Kd 3.7x10-8 M) [1]
Description: binding to SARS-CoV-2 Mpro
CoV 3C-like (main) protease SARS-CoV Inhibitor Inhibition 7.3 pIC50 - 1
pIC50 7.3 (IC50 5.5x10-8 M) [1]
Description: inhibition of SARS-CoV Mpro
CoV 3C-like (main) protease SARS-CoV-2 Inhibitor Inhibition 7.1 pIC50 - 1
pIC50 7.1 (IC50 7.2x10-8 M) [1]
Description: enzyme inhibition
CoV 3C-like (main) protease MERS-CoV Inhibitor Inhibition 6.0 pIC50 -
pIC50 6.0 (IC50 1.02x10-6 M)
Description: inhibition of MERS-CoV Mpro