cinchonine   Click here for help

GtoPdb Ligand ID: 13363

Synonyms: (+)-Cinchonine | D-Cinchonine
Compound class: Natural product
Comment: Cinchonine is an alkaloid phytochemical which is present in the South American shrub/tree Cinchona officinalis, one of the plants that is used for the production of quinine. It is structurally very similar quinine. Experimental evidence indicates that cinchonine can act as a GLP-1 receptor agonist, with associated findings in mouse models that support its potential as an oral agent to treat type 2 diabetes and non-alcoholic steatohepatitis (NASH) [1]. Molecular docking was used to analyse the likely binding characteristics of cinchonine for the GLP-1 receptor, and to predict the contact residues that mediate ligand docking into the receptor structure. Binding affinity was considered to be good by this methodology, but this should be confirmed by further in vitro exploration.

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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 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 35.83
Molecular weight 294.39
XLogP 1.39
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 C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=C3C=CC=C4)O
Isomeric SMILES C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
InChI InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
InChI Key KMPWYEUPVWOPIM-QAMTZSDWSA-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/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
Synonyms Click here for help
(+)-Cinchonine | D-Cinchonine
Database Links Click here for help
BindingDB Ligand 50370411
ChEBI CHEBI:27509
ChEMBL Ligand CHEMBL588619
GtoPdb PubChem SID 496703333
PubChem CID 90454
Search Google for chemical match using the InChIKey KMPWYEUPVWOPIM-QAMTZSDWSA-N
Search Google for chemicals with the same backbone KMPWYEUPVWOPIM
UniChem Compound Search for chemical match using the InChIKey KMPWYEUPVWOPIM-QAMTZSDWSA-N
UniChem Connectivity Search for chemical match using the InChIKey KMPWYEUPVWOPIM-QAMTZSDWSA-N

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MedChemExpress
Cinchonine (links to external site)
Cat. No. HY-Y0152