Human Metabolome Database Version 3.5

Showing metabocard for Quinine (HMDB14611)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:49 -0600
Update Date 2013-02-08 17:31:55 -0700
HMDB ID HMDB14611
Secondary Accession Numbers None
Metabolite Identification
Common Name Quinine
Description Quinine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 6'-Methoxycinchonidine
  2. 6'-Methoxycinchonine
  3. Quinine sulfate
  4. Quinine sulphate
  5. Quinine, Anhydrous
  6. Quinineanhydrous
  7. Quinoline Alkaloid
Chemical Formula C20H24N2O2
Average Molecular Weight 324.4168
Monoisotopic Molecular Weight 324.183778022
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 Number 130-95-0
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 Key LOUPRKONTZGTKE-WZBLMQSHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinolines and Derivatives
Sub Class Hydroxyquinolines
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • cinchona alkaloid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Piperidine
  • Pyridine
  • Quinuclidine
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Hydroxyquinolines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Analgesics, Non-Narcotic
  • Antimalarials
  • Muscle Relaxants, Central
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 57 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.34e-01 g/L Not Available
LogP 2.6 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.33 g/L ALOGPS
LogP 2.82 ALOGPS
LogP 2.51 ChemAxon
LogS -2.99 ALOGPS
pKa (strongest acidic) 13.89 ChemAxon
pKa (strongest basic) 9.05 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 45.59 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 94.69 ChemAxon
Polarizability 35.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00468
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00468
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00468 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002087
KNApSAcK ID C00002193 Link_out
Chemspider ID 84989 Link_out
KEGG Compound ID C06526 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Quinine Link_out
NuGOwiki Link HMDB14611 Link_out
Metagene Link HMDB14611 Link_out
METLIN ID Not Available
PubChem Compound 3034034 Link_out
PDB ID Not Available
ChEBI ID 15854 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
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 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions:
Quinine + NADPH + Oxygen unknown 3-Hydroxyquinine + NADP + Water details
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A7
Reactions: Not Available
Gene Name: CYP3A7
Uniprot ID: P24462 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Intermediate conductance calcium-activated potassium channel protein 4
Reactions: Not Available
Gene Name: KCNN4
Uniprot ID: O15554 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Solute carrier family 22 member 5
Reactions: Not Available
Gene Name: SLC22A5
Uniprot ID: O76082 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Multidrug resistance protein 1
Reactions: Not Available
Gene Name: ABCB1
Uniprot ID: P08183 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 4
Reactions: Not Available
Gene Name: SLC22A4
Uniprot ID: Q9H015 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 1
Reactions: Not Available
Gene Name: SLC22A1
Uniprot ID: O15245 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1A2
Reactions: Not Available
Gene Name: SLCO1A2
Uniprot ID: P46721 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier family 22 member 2
Reactions: Not Available
Gene Name: SLC22A2
Uniprot ID: O15244 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA