lufotrelvir   Click here for help

GtoPdb Ligand ID: 11249

Synonyms: PF-07304814 | PF07304814
PDB Ligand
Compound class: Synthetic organic
Comment: PF-07304814 is a SARS-CoV-2 3CL protease (Mpro) inhibitor from Pfizer. The structure of PF-07304814 is identical to that of the INN lufotrelvir (from proposed list 125, July 2021). PF-07304814's phosphate group (which improves solubility) is cleaved in vitro to release the active antiviral PF-00835231 [1-2]. PF-00835231 was originally developed as a SARS-CoV Mpro inhibitor in response to the 2002-2003 outbreak [3]. Like remdesivir, PF-07304814 is administered by intravenous infusion.
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 6
Rotatable bonds 15
Topological polar surface area 205.96
Molecular weight 552.2
XLogP -0.17
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COP(=O)(O)O)C[C@@H]1CCNC1=O)CC(C)C
Isomeric SMILES COc1cccc2c1cc([nH]2)C(=O)N[C@H](C(=O)N[C@H](C(=O)COP(=O)(O)O)C[C@@H]1CCNC1=O)CC(C)C
InChI InChI=1S/C24H33N4O9P/c1-13(2)9-18(28-24(32)19-11-15-16(26-19)5-4-6-21(15)36-3)23(31)27-17(10-14-7-8-25-22(14)30)20(29)12-37-38(33,34)35/h4-6,11,13-14,17-18,26H,7-10,12H2,1-3H3,(H,25,30)(H,27,31)(H,28,32)(H2,33,34,35)/t14-,17-,18-/m0/s1
InChI Key FQKALOFOWPDTED-WBAXXEDZSA-N
Bioactivity Comments
PF-00835231 potently inhibits replication of SARS-CoV-2 of the two major clades from clinical isolates in A549+ACE2 cells, and was statistically more potent than remdesivir [2].