cytisine   Click here for help

GtoPdb Ligand ID: 5347

Synonyms: baptitoxine | cytisin | cytisinicline | sophorine
PDB Ligand
Compound class: Natural product
Comment: Cytisine (INN: cytisinicline) is a naturally occurring phytochemical, found in leguminous plants including species of Laburnum and Cytisus. It interacts with central neuronal α4β2 subtype nicotinic acetylcholine receptors (nACh), with activity as a partial agonist [1-2].

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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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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 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 34.03
Molecular weight 190.11
XLogP 1.25
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 O=c1cccc2n1CC1CNCC2C1
Isomeric SMILES O=c1cccc2n1C[C@@H]1CNC[C@H]2C1
InChI InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
InChI Key ANJTVLIZGCUXLD-DTWKUNHWSA-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. Breining SR. (2004)
Recent developments in the synthesis of nicotinic acetylcholine receptor ligands.
Curr Top Med Chem, 4 (6): 609-29. [PMID:14965298]
2. Holladay MW, Dart MJ, Lynch JK. (1997)
Neuronal nicotinic acetylcholine receptors as targets for drug discovery.
J Med Chem, 40 (26): 4169-94. [PMID:9435889]
3. Rigotti NA, Benowitz NL, Prochaska J, Leischow S, Nides M, Blumenstein B, Clarke A, Cain D, Jacobs C. (2023)
Cytisinicline for Smoking Cessation: A Randomized Clinical Trial.
JAMA, 330 (2): 152-160. [PMID:37432430]
4. Rigotti NA, Benowitz NL, Prochaska JJ, Cain DF, Ball J, Clarke A, Blumenstein BA, Jacobs C. (2024)
Cytisinicline for Vaping Cessation in Adults Using Nicotine E-Cigarettes: The ORCA-V1 Randomized Clinical Trial.
JAMA Intern Med, 184 (8): 922-930. [PMID:38709500]