ML300   Click here for help

GtoPdb Ligand ID: 11657

Synonyms: compound 16e [PMID: 24080461] | ML-300
PDB Ligand
Compound class: Synthetic organic
Comment: ML300 was originally designed as a noncovalent, non-peptide-like inhibitor of SARS-CoV 3CL proteinase (Mpro) [2]. It also inhibits Mpro of SARS-CoV-2 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 108.36
Molecular weight 431.14
XLogP 2.45
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C1CC1)Nc1ccc(cc1)N(C(=O)Cn1nnc2c1cccc2)Cc1cscc1
Isomeric SMILES C1CC1C(=O)Nc1ccc(cc1)N(Cc1cscc1)C(=O)Cn1c2ccccc2nn1
InChI InChI=1S/C23H21N5O2S/c29-22(14-28-21-4-2-1-3-20(21)25-26-28)27(13-16-11-12-31-15-16)19-9-7-18(8-10-19)24-23(30)17-5-6-17/h1-4,7-12,15,17H,5-6,13-14H2,(H,24,30)
1. Han SH, Goins CM, Arya T, Shin WJ, Maw J, Hooper A, Sonawane DP, Porter MR, Bannister BE, Crouch RD et al.. (2022)
Structure-Based Optimization of ML300-Derived, Noncovalent Inhibitors Targeting the Severe Acute Respiratory Syndrome Coronavirus 3CL Protease (SARS-CoV-2 3CLpro).
J Med Chem, 65 (4): 2880-2904. [PMID:34347470]
2. Turlington M, Chun A, Tomar S, Eggler A, Grum-Tokars V, Jacobs J, Daniels JS, Dawson E, Saldanha A, Chase P et al.. (2013)
Discovery of N-(benzo[1,2,3]triazol-1-yl)-N-(benzyl)acetamido)phenyl) carboxamides as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors: identification of ML300 and noncovalent nanomolar inhibitors with an induced-fit binding.
Bioorg Med Chem Lett, 23 (22): 6172-7. [PMID:24080461]