Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2013-02-09 00:31:55 UTC
HMDB IDHMDB14611
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuinine
DescriptionQuinine is an alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood. [PubChem].
Structure
Thumb
Synonyms
  1. 6'-Methoxycinchonidine
  2. 6'-Methoxycinchonine
  3. Quinine sulfate
  4. Quinine sulphate
  5. Quinine, Anhydrous
  6. Quinineanhydrous
  7. Quinoline Alkaloid
Chemical FormulaC20H24N2O2
Average Molecular Weight324.4168
Monoisotopic Molecular Weight324.183778022
IUPAC Name(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional IUPAC Name(-)-quinine
CAS Registry Number130-95-0
SMILES
[H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12
InChI Identifier
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 KeyLOUPRKONTZGTKE-WZBLMQSHSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinolines and Derivatives
Sub ClassHydroxyquinolines
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • cinchona alkaloid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Piperidine
  • Pyridine
  • Quinuclidine
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentHydroxyquinolines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Analgesics, Non-Narcotic
  • Antimalarials
  • Muscle Relaxants, Central
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point57 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.34e-01 g/LNot Available
LogP2.6Not Available
Predicted Properties
PropertyValueSource
water solubility0.33 g/LALOGPS
logP2.82ALOGPS
logP2.51ChemAxon
logS-3ALOGPS
pKa (strongest acidic)13.89ChemAxon
pKa (strongest basic)9.05ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count1ChemAxon
polar surface area45.59ChemAxon
rotatable bond count4ChemAxon
refractivity94.69ChemAxon
polarizability35.96ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00468
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00468
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00468
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002087
KNApSAcK IDC00002193
Chemspider ID84989
KEGG Compound IDC06526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuinine
NuGOwiki LinkHMDB14611
Metagene LinkHMDB14611
METLIN IDNot Available
PubChem Compound3034034
PDB IDNot Available
ChEBI ID15854
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23. Pubmed: 8143397

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Reactions
Quinine + NADPH + Oxygen unknown 3-Hydroxyquinine + NADP + Waterdetails
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP2C8
Uniprot ID:
P10632

Transporters

Gene Name:
SLC22A5
Uniprot ID:
O76082
Gene Name:
ABCB1
Uniprot ID:
P08183
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Gene Name:
SLC22A1
Uniprot ID:
O15245
Gene Name:
SLC22A2
Uniprot ID:
O15244