quinine

Ligand id: 2510

Name: quinine

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Natural product or derivative
Ligand families/groups Antimalarial ligands
Approved drug? Yes (FDA (2005, as quinine sulfate, previous history unspecified))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(R)-[(4S,5R,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol
Synonyms
GNF-Pf-506 | Qualaquin® | Quinate® | quinine bisulphate | quinine sulfate
Comments
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.
Database Links
BitterDB Ligand 38
CAS Registry No. 130-95-0 (source: Scifinder)
ChEBI CHEBI:15854
ChEMBL Ligand CHEMBL170
DrugBank Ligand DB00468
GtoPdb PubChem SID 135652709
PubChem CID 3034034
RCSB PDB Ligand QI9
Search Google for chemical match using the InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
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Search UniChem for chemical match using the InChIKey LOUPRKONTZGTKE-WZBLMQSHSA-N
Search UniChem for chemicals with the same backbone LOUPRKONTZGTKE
Wikipedia Quinine