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
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form PF-00835231
IUPAC Name Click here for help
[(3S)-3-[(2S)-2-[(4-methoxy-1H-indol-2-yl)formamido]-4-methylpentanamido]-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butoxy]phosphonic acid
International Nonproprietary Names Click here for help
INN number INN
12095 lufotrelvir
Synonyms Click here for help
PF-07304814 | PF07304814
Database Links Click here for help
GtoPdb PubChem SID 434122309
PubChem CID 154699467
RCSB PDB Ligand 80I, 80I
Search Google for chemical match using the InChIKey FQKALOFOWPDTED-WBAXXEDZSA-N
Search Google for chemicals with the same backbone FQKALOFOWPDTED
Search PubMed clinical trials lufotrelvir
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Search PubMed titles/abstracts lufotrelvir
UniChem Compound Search for chemical match using the InChIKey FQKALOFOWPDTED-WBAXXEDZSA-N
UniChem Connectivity Search for chemical match using the InChIKey FQKALOFOWPDTED-WBAXXEDZSA-N