arecoline   Click here for help

GtoPdb Ligand ID: 296

Synonyms: methylarecaiden | methylarecaidin | taeniolin
Compound class: Natural product
Comment: Arecoline is an alkaloid derived from the betel nut. It acts as a cholinomimetic.
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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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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 29.54
Molecular weight 155.09
XLogP 0.17
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)C1=CCCN(C1)C
Isomeric SMILES COC(=O)C1=CCCN(C1)C
InChI InChI=1S/C8H13NO2/c1-9-5-3-4-7(6-9)8(10)11-2/h4H,3,5-6H2,1-2H3
InChI Key HJJPJSXJAXAIPN-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Christie JE, Shering A, Ferguson J, Glen AI. (1981)
Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia.
Br J Psychiatry, 138: 46-50. [PMID:7023592]
2. Ghelardini C, Galeotti N, Lelli C, Bartolini A. (2001)
M1 receptor activation is a requirement for arecoline analgesia.
Farmaco, 56 (5-7): 383-5. [PMID:11482763]
3. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
4. Mei L, Lai J, Roeske WR, Fraser CM, Venter JC, Yamamura HI. (1989)
Pharmacological characterization of the M1 muscarinic receptors expressed in murine fibroblast B82 cells.
J Pharmacol Exp Ther, 248 (2): 661-70. [PMID:2537406]
5. Ozenil M, Pacher K, Balber T, Vraka C, Roller A, Holzer W, Spreitzer H, Mitterhauser M, Wadsak W, Hacker M et al.. (2020)
Enhanced arecoline derivatives as muscarinic acetylcholine receptor M1 ligands for potential application as PET radiotracers.
Eur J Med Chem, 204: 112623. [PMID:32717485]
6. Richards MH, van Giersbergen PL. (1995)
Human muscarinic receptors expressed in A9L and CHO cells: activation by full and partial agonists.
Br J Pharmacol, 114 (6): 1241-9. [PMID:7620715]
7. Xie DP, Chen LB, Liu CY, Zhang CL, Liu KJ, Wang PS. (2004)
Arecoline excites the colonic smooth muscle motility via M3 receptor in rabbits.
Chin J Physiol, 47 (2): 89-94. [PMID:15481791]
8. Yang YR, Chang KC, Chen CL, Chiu TH. (2000)
Arecoline excites rat locus coeruleus neurons by activating the M2-muscarinic receptor.
Chin J Physiol, 43 (1): 23-8. [PMID:10857465]