naphthylvinylmethylpyridine   Click here for help

GtoPdb Ligand ID: 8807

Synonyms: (E)-4-(1-naphthylvinyl)pyridine methochloride | compound 2 [PMID: 3351860]
Compound class: Synthetic organic
Comment: Compound 2 is one of a series of compounds investigated as inhibitors of choline O-acetyltransferase (CHAT, a.k.a. choline acetyltransferase) [1], in the search for compounds with the ability to provide protection against nerve agent poisoning.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 3.88
Molecular weight 246.13
XLogP 6.31
No. Lipinski's rules broken 1
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Canonical SMILES C[n+]1ccc(cc1)C=Cc1cccc2c1cccc2
Isomeric SMILES C[n+]1ccc(cc1)/C=C/c1cccc2c1cccc2
InChI InChI=1S/C18H16N/c1-19-13-11-15(12-14-19)9-10-17-7-4-6-16-5-2-3-8-18(16)17/h2-14H,1H3/q+1/b10-9+
Bioactivity Comments
Note that some bioactivity data may be attributed to the chloride salt (PubChem CID 44379511). Inhibitory activity towards isolated choline acetyltransferase from Lactobacillus plantarum (IC50 700 nM) and bovine caudate nucleus (IC50 650 nM) haa been published [2].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
choline O-acetyltransferase Mm Inhibitor Inhibition 6.5 pIC50 - 1
pIC50 6.5 (IC50 3.4x10-7 M) [1]