compound 23 [PMID: 17125252]   Click here for help

GtoPdb Ligand ID: 8756

Compound class: Synthetic organic
Comment: Compound 23 is a nicotine analogue which inhibits the major nicotine metabolising enzyme, cytochrome P450 2A6 (CYP2A6) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 54.26
Molecular weight 189.06
XLogP 1.77
No. Lipinski's rules broken 0
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Canonical SMILES NCc1ccc(s1)c1ccccc1
Isomeric SMILES NCc1ccc(s1)c1ccccc1
InChI InChI=1S/C11H11NS/c12-8-10-6-7-11(13-10)9-4-2-1-3-5-9/h1-7H,8,12H2
Bioactivity Comments
Although compound 23 was designed as a CYP2A6 inhibitor, it inhibits CYP2E1 with a 15-fold lower inhibitory constant (Ki) [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CYP2E1 Hs Inhibitor Inhibition 7.4 pKi - 1
pKi 7.4 (Ki 4x10-8 M) [1]
CYP2A6 Hs Inhibitor Inhibition 6.2 pKi - 1
pKi 6.2 (Ki 6x10-7 M) [1]