Showing Compound Quinine bisulfate (FDB019895)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:39 UTC

Update date

2018-05-29 01:43:50 UTC

Primary ID

FDB019895

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Quinine bisulfate

Description

Bitter 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 Number

549-56-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
6'-Methoxycinchonan-9-ol sulfate, (8alpha,9R)-, (1:1)	biospider
8alpha,9R-6'-Methoxycinchonan-9-ol, sulfate (1:1) salt	biospider
Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-, sulfate (1:1)	biospider
FEMA 2975	db_source
Quinine bisulfate	db_source
Quinine bisulfuric acid	Generator
Quinine bisulphate	Generator
Quinine bisulphuric acid	Generator
Quinine sulfate (1:1)	biospider

Showing 1 to 9 of 9 entries

Predicted Properties

Property	Value	Source
logP	2.51	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.69 m³·mol⁻¹	ChemAxon
Polarizability	35.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H42N2O17S2

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 Identifier

InChI=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 Key

QRINDWCWGOHSTN-FTCXZRKKSA-N

Isomeric SMILES

O.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 Weight

646.681

Monoisotopic Molecular Weight

646.192489308

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cinchona alkaloids

Sub Class

Not Available

Direct Parent

Cinchona 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	10.8 mg/mL at 25 oC	SEIDELL,A (1941)
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40183

CRC / DFC (Dictionary of Food Compounds) ID

CFC28-A:MFO58-X

EAFUS ID

3278

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1034311

SuperScent ID

Not Available

Wikipedia ID

Quinine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Show entries

Search:

Showing 1 to 1 of 1 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Quinine bisulfate (FDB019895)

Structure for FDB019895 (Quinine bisulfate)