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 or derivative
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
Selectivity at GPCRs
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R14 Hs Agonist Agonist - - - 4
⤷ [4]
Description: Threshold=10 μM
TAS2R40 Hs Agonist Agonist - - - 4
⤷ [4]
Description: Threshold=10 μM
Selectivity at ion channels
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
K2P18.1 N/A Channel blocker - - - 1x10-4 - 2x10-4
⤷ Conc range: 1x10-4 - 2x10-4 M
Kv2.2 Hs Channel blocker - 4.9 pIC50 - 5
⤷ pIC50 4.9 [5]
VRAC Hs Channel blocker - - - -
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Selectivity at transporters
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasma membrane monoamine transporter Hs Inhibitor Inhibition 4.6 pKi - 3,6
⤷ pKi 4.6 (Ki 2.69x10-5 M) [3,6]
Selectivity at other protein targets
Key to terms and symbols Click on species/strain names for details Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum purine nucleoside phosphorylase Pf

Plasmodium falciparum

P. falciparum (Pf) is one of five protozoan parasite species of the genus Plasmodium that cause malaria in humans. Pf is responsible for the majority of malaria related deaths and is the most prevalent species in sub-Saharan Africa.
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 Inhibitor - 6.9 pKi - 2
⤷ pKi 6.9 (Ki 1.38x10-7 M) [2]
Ligand mentioned in the following text fields
5-HT3 receptors comments
Organic cation transporters (OCT) comments