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Showing Compound Quinine (FDB002087)

Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2018-05-29 00:33:54 UTC
Primary IDFDB002087
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuinine
DescriptionIt is used in tonics and bitter drinks Quinine is a natural white crystalline alkaloid having antipyretic, antimalarial, analgesic, anti-inflammatory properties and a bitter taste. It is a stereoisomer of quinidine which, unlike quinine, is an anti-arrhythmic. Though it has been synthesized in the lab, the bark of the cinchona tree is the only known natural source of quinine. Quinine was the first effective treatment for malaria caused by Plasmodium falciparum, appearing in therapeutics in the 17th century. It remained the antimalarial drug of choice until the 1940s, when other drugs replaced it.
CAS Number130-95-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(-)-QuinineChEBI
(8S,9R)-QuinineChEBI
(R)-(-)-QuinineChEBI
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanolChEBI
6'-MethoxycinchonidineChEBI
ChininChEBI
ChinineChEBI
ChininumChEBI
QuininaChEBI
MyoquinMeSH
SurquinaMeSH
BiquinateMeSH
QuinimaxMeSH
Quinine bisulfateMeSH
Quinine sulfateMeSH
QuinoctalMeSH
QuinsonMeSH
QuinsulMeSH
Bisulfate, quinineMeSH
Hydrochloride, quinineMeSH
LegatrimMeSH
QuinammMeSH
QuinbisanMeSH
QuinbisulMeSH
Quinine lafranMeSH
Quinine sulphateMeSH
Quinine-odanMeSH
Sulfate, quinineMeSH
Sulphate, quinineMeSH
QuindanMeSH
Quinine hydrochlorideMeSH
StremaMeSH
6'-MethoxycinchonineHMDB
Quinine, anhydrousHMDB
QuinineanhydrousHMDB
Quinoline alkaloidHMDB
Aventis brand OF quinine bisulfateMeSH, HMDB
Fawns and mcallan brand OF quinine sulfateMeSH, HMDB
Foy brand OF quinine sulfateMeSH, HMDB
Plough brand OF quinine sulfateMeSH, HMDB
Fawns and mcallan brand OF quinine bisulfateMeSH, HMDB
Hoechst brand OF quinine sulfateMeSH, HMDB
Lafran brand OF quinine hydrochlorideMeSH, HMDB
Alphapharm brand OF quinine sulfateMeSH, HMDB
Innotech brand OF quinine hydrochlorideMeSH, HMDB
Odan brand OF quinine sulfateMeSH, HMDB
Prosana brand OF quinine bisulfateMeSH, HMDB
(8-alpha,9R)-6'-Methoxycinchonan-9-olbiospider
(8S,9R)-6'-Methoxycinchonan-9-olbiospider
(R)-(-)-quininemanual
(R)-(-)-Quinine, 6-methoxycinchonidinebiospider
α-(6-Methoxy-4-quinoyl)-5-vinyl-2-quinclidinemethanolbiospider
6-Methoxy-quinolinbiospider
6-Methoxycinchoninebiospider
6'-Methoxycinchonan-9-ol, 9CIdb_source
Cinchonan-9-ol, 6'-methoxy-biospider
Cinchonan-9-ol, 6'-methoxy-, (8α,9R)-biospider
Cinchonan-9-ol, 6'-methoxy-, (8a,9R)-biospider
Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-biospider
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 Area45.59 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.69 m³·mol⁻¹ChemAxon
Polarizability35.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H24N2O2
IUPAC name(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight324.4168
Monoisotopic Molecular Weight324.183778022
Classification
Description Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • 4-quinolinemethanol
  • Quinoline
  • Anisole
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 74.05%; H 7.46%; N 8.63%; O 9.86%DFC
Melting PointMp 177° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility0.5 mg/mL at 15 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.44HANSCH,C ET AL. (1995)
Experimental pKapKa2 4.21 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -158 (-145) (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSQuinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4r-1901000000-8176add5a84f7ae1eb69Spectrum
Predicted GC-MSQuinine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05g0-7947000000-ee233460f7e7fbb00ca7Spectrum
Predicted GC-MSQuinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00ai-7930000000-eb63f68d11153566b0272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00c0-7910000000-c0d16dda8d8a74dd16572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0059-5945000000-dff1a74853685996f9652021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-004i-0009000000-4cf6c66b2059468cd1e32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0009000000-d4367d77a81731ba36542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00ai-7930000000-94e16a407d113a5472402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0059-5945000000-ddc4f19918fbae8ffe0c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0fc0-6900000000-8bb456f41e7cb82dfcf92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0fc0-6900000000-f458cccf839df1d5239b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-00c0-7910000000-4b620f5ca762298602e72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0019000000-0f42379f2989cf204f722016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0729000000-5a0d8aa890e6c737bf452016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0920000000-70e4fed1a61c38cf53fb2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-e84ce15e838ff8ac33f62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0229000000-b87ca7a53d952af7505e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0540-0920000000-12d8977ce43e168f84532016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-2125f5c1412244f91fb32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0109000000-1096d980c779fca1eb3f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0920000000-468db2e8e8941541468c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-9c5f7ffbd0d69038e6da2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-0914000000-92707d10764c62ebe3202021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-9e1ce60a980eb9551f332021-09-24View Spectrum
NMRNot Available
ChemSpider ID84989
ChEMBL IDCHEMBL170
KEGG Compound IDC06526
Pubchem Compound ID3034034
Pubchem Substance IDNot Available
ChEBI ID15854
Phenol-Explorer IDNot Available
DrugBank IDDB00468
HMDB IDHMDB14611
CRC / DFC (Dictionary of Food Compounds) IDCFC28-A:CFC28-A
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002193
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDQuinine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference