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))
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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2D Structure
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Physico-chemical Properties
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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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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 ion channels
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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 - 4
pIC50 4.9 [4]
VRAC Hs Channel blocker - - - -
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasma membrane monoamine transporter Hs Inhibitor Inhibition 4.6 pKi - 3,5
pKi 4.6 (Ki 2.69x10-5 M) [3,5]
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Plasmodium falciparum purine nucleoside phosphorylase Pf Inhibitor - 6.9 pKi - 2
pKi 6.9 (Ki 1.38x10-7 M) [2]
Ligand mentioned in the following text fields