avoralstat   Click here for help

GtoPdb Ligand ID: 11584

Synonyms: BCX-4161 | BCX4161
PDB Ligand
Compound class: Synthetic organic
Comment: Avoralstat (BCX-4161) is a small molecule, oral plasma kallikrein (a serine protease that generates bradykinin from kininogen) inhibitor [3]. Data pubished in 2021 indicate that avoralstat inhibits TMPRSS2 (a protease required for spike protein-mediated SARS-CoV-2 viral entry via ACE2) with comparable inhibitory activity to camostat [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 12
Topological polar surface area 167.49
Molecular weight 513.2
XLogP 1.7
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(c(cc1C=C)C(=O)Nc1ccc(cc1)C(=N)N)c1ccc(nc1C(=O)O)C(=O)NCC1CC1
Isomeric SMILES COc1cc(c(cc1C=C)C(=O)Nc1ccc(cc1)C(=N)N)c1ccc(nc1C(=O)O)C(=O)NCC1CC1
InChI InChI=1S/C28H27N5O5/c1-3-16-12-21(26(34)32-18-8-6-17(7-9-18)25(29)30)20(13-23(16)38-2)19-10-11-22(33-24(19)28(36)37)27(35)31-14-15-4-5-15/h3,6-13,15H,1,4-5,14H2,2H3,(H3,29,30)(H,31,35)(H,32,34)(H,36,37)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
3-[2-[(4-carbamimidoylphenyl)carbamoyl]-4-ethenyl-5-methoxyphenyl]-6-(cyclopropylmethylcarbamoyl)pyridine-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
10052 avoralstat
Synonyms Click here for help
BCX-4161 | BCX4161
Database Links Click here for help
CAS Registry No. 918407-35-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297502
DrugBank Ligand DB12120
GtoPdb PubChem SID 442878618
PubChem CID 86566678
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UniChem Compound Search for chemical match using the InChIKey TUWMKPVJGGWGNL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey TUWMKPVJGGWGNL-UHFFFAOYSA-N