Showing Compound Quinine (FDB002087)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2018-05-29 00:33:54 UTC

Primary ID

FDB002087

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Quinine

Description

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

130-95-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Search:

Synonym	Source
(-)-Quinine	ChEBI
(8-alpha,9R)-6'-Methoxycinchonan-9-ol	biospider
(8S,9R)-6'-Methoxycinchonan-9-ol	biospider
(8S,9R)-Quinine	ChEBI
(R)-(-)-Quinine	ChEBI
(R)-(-)-quinine	manual
(R)-(-)-Quinine, 6-methoxycinchonidine	biospider
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol	ChEBI
6'-Methoxycinchonan-9-ol, 9CI	db_source
6'-Methoxycinchonidine	ChEBI

Showing 1 to 10 of 59 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.51	ChemAxon
logS	-3	ALOGPS
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	35.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H24N2O2

IUPAC name

(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

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

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 Weight

324.4168

Monoisotopic Molecular Weight

324.183778022

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.

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
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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

cinchona alkaloid (CHEBI:15854 )

Ontology

Pulmonary edema

Vascular disorders:

Hypotension

Renal and urinary disorders:

Hemoglobinuria

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Neuromuscular agent:

Muscle relaxant

Household products:

Antimicrobial agent:

Antimalarial

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	3.44	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 4.21 (20°)	DFC
Experimental Water Solubility	0.5 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 74.05%; H 7.46%; N 8.63%; O 9.86%	DFC
Melting Point	Mp 177° (anhyd.)	DFC
Optical Rotation	[a]D -158 (-145) (EtOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Quinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4r-1901000000-8176add5a84f7ae1eb69	Spectrum
Predicted GC-MS	Quinine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05g0-7947000000-ee233460f7e7fbb00ca7	Spectrum
Predicted GC-MS	Quinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00ai-7930000000-eb63f68d11153566b027	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00c0-7910000000-c0d16dda8d8a74dd1657	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0059-5945000000-dff1a74853685996f965	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-004i-0009000000-4cf6c66b2059468cd1e3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0009000000-d4367d77a81731ba3654	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00ai-7930000000-94e16a407d113a547240	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0059-5945000000-ddc4f19918fbae8ffe0c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0fc0-6900000000-8bb456f41e7cb82dfcf9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0fc0-6900000000-f458cccf839df1d5239b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00c0-7910000000-4b620f5ca762298602e7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-0019000000-0f42379f2989cf204f72	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-0729000000-5a0d8aa890e6c737bf45	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-0920000000-70e4fed1a61c38cf53fb	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0109000000-e84ce15e838ff8ac33f6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-0229000000-b87ca7a53d952af7505e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0540-0920000000-12d8977ce43e168f8453	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-2125f5c1412244f91fb3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0109000000-1096d980c779fca1eb3f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0920000000-468db2e8e8941541468c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0019000000-9c5f7ffbd0d69038e6da	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abi-0914000000-92707d10764c62ebe320	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-9e1ce60a980eb9551f33	2021-09-24	View Spectrum