quinine   Click here for help

GtoPdb Ligand ID: 2510

Synonyms: GNF-Pf-506 | Qualaquin® | Quinate® | quinine bisulphate | quinine sulfate
Approved drug PDB Ligand Antimalarial Ligand
quinine is an approved drug (FDA (2005, as quinine sulfate, previous history unspecified))
Compound class: Natural product
Comment: First extracted from the bark of the cinchona tree and used as an antimalarial medicine, quinine has also been synthesized in the laboratory [1].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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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
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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 45.59
Molecular weight 324.18
XLogP 2.6
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 C=CC1CN2CCC1CC2C(c1ccnc2c1cc(OC)cc2)O
Isomeric SMILES C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O
InChI InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
InChI Key LOUPRKONTZGTKE-WZBLMQSHSA-N
Classification Click here for help
Compound class Natural product
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2005, as quinine sulfate, previous history unspecified))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(R)-[(4S,5R,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol
Synonyms Click here for help
GNF-Pf-506 | Qualaquin® | Quinate® | quinine bisulphate | quinine sulfate
Database Links Click here for help
Specialist databases
GPCRdb Ligand quinine
Other databases
BitterDB Ligand 38
CAS Registry No. 130-95-0 (source: Scifinder)
ChEBI CHEBI:15854
ChEMBL Ligand CHEMBL170
DrugBank Ligand DB00468
DrugCentral Ligand 4523
GtoPdb PubChem SID 135652709
PubChem CID 3034034
RCSB PDB Ligand QI9
Search Google for chemical match using the InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
Search Google for chemicals with the same backbone LOUPRKONTZGTKE
UniChem Compound Search for chemical match using the InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
UniChem Connectivity Search for chemical match using the InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
Wikipedia Quinine