Ligand id: 2585

Name: nicotine

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Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 16.13
Molecular weight 162.12
XLogP 1.13
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Bioactivity Comments
Data show a range of bioactivity levels at various heterologously expressed human nACh heteromeric ion channels. Kis as follows; α2β4=9900nM [6], α3β2=14nM [1], α3β4=187nM [1], α4β2=1nM [4,7]. Due to the heterogeneity of nACh channels we have not tagged a primary drug target for nicotine, although the α4β2 is reported to be the predominant high affinity subtype in the brain which mediates nicotine addiction [2-3].
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
nicotinic acetylcholine receptor α4 subunit Hs Agonist Agonist 8.7 pKi - 5
pKi 8.7 (Ki 2.2x10-9 M) α4β2 [5]
Description: In vitro affinity for recombinant human α4β2 receptors in membranes from transfected CHO-K1 cells, determined by displacement of [3H]-(−)-cytisine.
nicotinic acetylcholine receptor α3 subunit Hs Agonist Agonist 5.8 pKi - 5
pKi 5.8 (Ki 1.744x10-6 M) α3β4 [5]
TRPA1 Hs Activator Activation 4.8 pEC50 - 8
pEC50 4.8 (EC50 1.7x10-5 M) non-covalent [8]
Voltage: -75.0 mV
Description: Patch clamp
Conditions: CHO cells expressing mouse or human TRPA1
Kv4.3 Rn Channel blocker - 7.4 pIC50 - 9
pIC50 7.4 [9]
nicotinic acetylcholine receptor α9 subunit Hs Antagonist Antagonist - - -
nicotinic acetylcholine receptor α10 subunit Hs Antagonist Antagonist - - -
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