compound 73 [WO2017106607A1]   Click here for help

GtoPdb Ligand ID: 11307

Synonyms: enpatoran (proposed INN)
PDB Ligand
Compound class: Synthetic organic
Comment: This chemical structure (as the IUPAC name) was obtained from the special release of proposed INNs for COVID-related therapeutics that was published by the WHO in October 2020. The INN structure was identified as being identical to compound 73 from Merck's patent WO2017106607A1 (2017) in which it is claimed as a Toll-like receptor (TLR)7 and TLR8 antagonist for the treatment of immune disorders [2]. We speculate that this is Merck's clinical lead M5049, which is expected to prevent activation of TLR7/8 which detect single-stranded RNA from viruses including SARS-CoV-2 [1]. M5049 is administered orally. At the time of generating this entry (Nov 2020) there had been no formal name>structure disclosure of M5049. We will update this record when new details are published.
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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 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 65.94
Molecular weight 320.12
XLogP 3.24
No. Lipinski's rules broken 0
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 N#Cc1ccc(c2c1nccc2)N1C[C@H](N)C[C@@H](C1)C(F)(F)F
Isomeric SMILES N#Cc1ccc(c2c1nccc2)N1C[C@H](N)C[C@@H](C1)C(F)(F)F
InChI InChI=1S/C16H15F3N4/c17-16(18,19)11-6-12(21)9-23(8-11)14-4-3-10(7-20)15-13(14)2-1-5-22-15/h1-5,11-12H,6,8-9,21H2/t11-,12+/m0/s1
InChI Key BJXYHBKEQFQVES-NWDGAFQWSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[(3R,5S)-3-amino-5-(trifluoromethyl)piperidin-1-yl]quinoline-8-carbonitrile
Synonyms Click here for help
enpatoran (proposed INN)
Database Links Click here for help
CAS Registry No. 2101938-42-3 (source: WHO INN record)
GtoPdb PubChem SID 434321742
PubChem CID 129240620
RCSB PDB Ligand QLH
Search Google for chemical match using the InChIKey BJXYHBKEQFQVES-NWDGAFQWSA-N
Search Google for chemicals with the same backbone BJXYHBKEQFQVES
UniChem Compound Search for chemical match using the InChIKey BJXYHBKEQFQVES-NWDGAFQWSA-N
UniChem Connectivity Search for chemical match using the InChIKey BJXYHBKEQFQVES-NWDGAFQWSA-N