compound 2i [PMID: 23245752]   Click here for help

GtoPdb Ligand ID: 11630

PDB Ligand
Compound class: Synthetic organic
Comment: Compound 2i was originally reported as a tripeptide-type SARS-CoV 3CL protease inhibitor [1]. It has subsequently been shown to inhibit SARS-CoV-2 3CL protease [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 18
Topological polar surface area 183.83
Molecular weight 635.28
XLogP 3.79
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)c1nc2c(s1)cccc2)C[C@@H]1CCNC1=O)CC(C)C)C(C)C)OCc1ccccc1
Isomeric SMILES O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)c1nc2c(s1)cccc2)C[C@@H]1CCNC1=O)CC(C)C)C(C)C)OCc1ccccc1
InChI InChI=1S/C33H41N5O6S/c1-19(2)16-25(36-31(42)27(20(3)4)38-33(43)44-18-21-10-6-5-7-11-21)30(41)35-24(17-22-14-15-34-29(22)40)28(39)32-37-23-12-8-9-13-26(23)45-32/h5-13,19-20,22,24-25,27H,14-18H2,1-4H3,(H,34,40)(H,35,41)(H,36,42)(H,38,43)/t22-,24-,25-,27-/m0/s1
InChI Key KSCRVOKQPYZBHZ-IXPOFIJOSA-N
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 7.0 pIC50 - 2
pIC50 7.0 (IC50 9.4x10-8 M) [2]
CoV 3C-like (main) protease SARS-CoV Inhibitor Inhibition 5.8 pIC50 - 1
pIC50 5.8 (IC50 1.7x10-6 M) [1]