nicotine   Click here for help

GtoPdb Ligand ID: 2585

Synonyms: Nicorette® | Nicotrol®
Approved drug PDB Ligand
nicotine is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Nicotine is a natural alkaloid of the tobacco plant. It is an addictive stimulant, which is an agonist of most nicotinic acetylcholine receptors (nAChRs) (it is an antagonist of the nAChRα9 and nAChRα10 receptor subtypes).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: nicotine

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 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
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 CN1CCCC1c1cccnc1
Isomeric SMILES CN1CCC[C@H]1c1cccnc1
InChI InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
InChI Key SNICXCGAKADSCV-JTQLQIEISA-N
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
CYP2A6
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 - - -
⤷ (α9)5
α9α10
nicotinic acetylcholine receptor α10 subunit Hs Antagonist Antagonist - - -
⤷ α9α10
Ligand mentioned in the following text fields
Nicotinic acetylcholine receptors (nACh) comments