compound 15c [PMID: 34865476]   Click here for help

GtoPdb Ligand ID: 11834

Compound class: Synthetic organic
Comment: Compound 15c is one of the most potent SARS-CoV-2 Mpro inhibitors, from an extensive series with IC50 values around 200-400 nM [1]. The chemical structure shown here was rendered using the SMILES provided in the primary reference. 15c was crystalised in complex with SARS-CoV-2 Mpro and the structural data is available from the PDB (ID 7T4B).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 16
Topological polar surface area 168.51
Molecular weight 625.22
XLogP 2.76
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES [Na]OS(=O)(=O)C([C@H](C[C@@H]1CCNC1=O)NC(=O)[C@@H](NC(=O)OC(c1ccccc1)C1CCC(CC1)(F)F)CC(C)C)O
Isomeric SMILES O=C(N[C@H](C(=O)N[C@H](C(S(=O)(=O)O[Na])O)C[C@H]1C(=O)NCC1)CC(C)C)OC(C1CCC(F)(F)CC1)c1ccccc1
InChI InChI=1S/C27H39F2N3O8S.Na/c1-16(2)14-20(24(34)31-21(25(35)41(37,38)39)15-19-10-13-30-23(19)33)32-26(36)40-22(17-6-4-3-5-7-17)18-8-11-27(28,29)12-9-18;/h3-7,16,18-22,25,35H,8-15H2,1-2H3,(H,30,33)(H,31,34)(H,32,36)(H,37,38,39);/q;+1/p-1/t19-,20-,21-,22?,25?;/m0./s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4,4-difluorocyclohexyl)(phenyl)methyl N-[(1S)-1-{[(2S)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]-1-[(sodiooxy)sulfonyl]propan-2-yl]carbamoyl}-3-methylbutyl]carbamate
Database Links Click here for help
GtoPdb PubChem SID 461663390
PubChem CID 162641715
Search Google for chemical match using the InChIKey DVWOYOSIEJRHKW-UIRZNSHLSA-M
Search Google for chemicals with the same backbone DVWOYOSIEJRHKW
UniChem Compound Search for chemical match using the InChIKey DVWOYOSIEJRHKW-UIRZNSHLSA-M
UniChem Connectivity Search for chemical match using the InChIKey DVWOYOSIEJRHKW-UIRZNSHLSA-M