compound 15l [PMID: 34242027]   Click here for help

GtoPdb Ligand ID: 11606

PDB Ligand
Compound class: Synthetic organic
Comment: This compound is a covalent inhibitor of SARS-CoV-2 3CL protease (Mpro) [1]. It is stable in human and mouse plasma, and is not toxic against experimental cell lines (Vero E6 and A549 cells).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 16
Topological polar surface area 168.58
Molecular weight 633.32
XLogP 3.69
No. Lipinski's rules broken 1
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Canonical SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COC(=O)c1c(C)cc(nc1C)C)C[C@@H]1CCCNC1=O)CC(C)C
Isomeric SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COC(=O)c1c(C)cc(nc1C)C)C[C@@H]1CCCNC1=O)CC(C)C
InChI InChI=1S/C34H43N5O7/c1-18(2)13-26(39-33(43)27-16-23-24(37-27)10-7-11-29(23)45-6)32(42)38-25(15-22-9-8-12-35-31(22)41)28(40)17-46-34(44)30-19(3)14-20(4)36-21(30)5/h7,10-11,14,16,18,22,25-26,37H,8-9,12-13,15,17H2,1-6H3,(H,35,41)(H,38,42)(H,39,43)/t22-,25-,26-/m0/s1
1. Bai B, Belovodskiy A, Hena M, Kandadai AS, Joyce MA, Saffran HA, Shields JA, Khan MB, Arutyunova E, Lu J et al.. (2022)
Peptidomimetic α-Acyloxymethylketone Warheads with Six-Membered Lactam P1 Glutamine Mimic: SARS-CoV-2 3CL Protease Inhibition, Coronavirus Antiviral Activity, and in Vitro Biological Stability.
J Med Chem, 65 (4): 2905-2925. [PMID:34242027]