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Showing Compound Quinine bisulfate (FDB019895)

Record Information
Version1.0
Creation date2010-04-08 22:14:39 UTC
Update date2018-05-29 01:43:50 UTC
Primary IDFDB019895
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuinine bisulfate
DescriptionBitter flavouring It 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 Number549-56-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Quinine bisulfuric acidGenerator
Quinine bisulphateGenerator
Quinine bisulphuric acidGenerator
6'-Methoxycinchonan-9-ol sulfate, (8alpha,9R)-, (1:1)biospider
8alpha,9R-6'-Methoxycinchonan-9-ol, sulfate (1:1) saltbiospider
Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-, sulfate (1:1)biospider
FEMA 2975db_source
Quinine bisulfatedb_source
Quinine sulfate (1:1)biospider
Predicted Properties
PropertyValueSource
logP2.51ChemAxon
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
Polarizability35.97 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H42N2O17S2
IUPAC name(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol bis(sulfuric acid) heptahydrate
InChI IdentifierInChI=1S/C20H24N2O2.2H2O4S.7H2O/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;2*1-5(2,3)4;;;;;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*(H2,1,2,3,4);7*1H2/t13-,14-,19-,20+;;;;;;;;;/m0........./s1
InChI KeyQRINDWCWGOHSTN-FTCXZRKKSA-N
Isomeric SMILESO.O.O.O.O.O.O.OS(O)(=O)=O.OS(O)(=O)=O.COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1
Average Molecular Weight646.681
Monoisotopic Molecular Weight646.192489308
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
  • Sulfuric acid
  • Aralkylamine
  • Benzenoid
  • Pyridine
  • Piperidine
  • Heteroaromatic compound
  • Organic sulfuric acid or derivatives
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Aromatic alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water Solubility10.8 mg/mL at 25 oCSEIDELL,A (1941)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40183
CRC / DFC (Dictionary of Food Compounds) IDCFC28-A:MFO58-X
EAFUS ID3278
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034311
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
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference