Showing Compound 3-Hydroxyquinine (FDB022421)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:45 UTC

Update date

2015-07-21 06:57:12 UTC

Primary ID

FDB022421

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Hydroxyquinine

Description

3-Hydroxyquinine 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. 3-Hydroxyquinine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyquinine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxyquinine.

CAS Number

53467-23-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3-Hydroxyquinidine	HMDB, MeSH
3-hydroxyquinidine	hmdb
3-Hydroxyquinidine, (3alpha,9S)-isomer	MeSH, HMDB
3-Hydroxyquinidine, (8alpha,9R)-isomer	MeSH, HMDB
3-Hydroxyquinine	MeSH
6'-Methoxycinchonan-3,9-diol	HMDB

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.14 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.67	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.55	ChemAxon
pKa (Strongest Basic)	8.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.91 m³·mol⁻¹	ChemAxon
Polarizability	36.89 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

C20H24N2O3

IUPAC name

(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

InChI Identifier

InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1

InChI Key

BSRUJCFCZKMFMB-ZNYHDOEXSA-N

Isomeric SMILES

[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

Average Molecular Weight

340.4162

Monoisotopic Molecular Weight

340.178692644

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
Tertiary alcohol
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic alcohol
Alcohol
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Malaria

Disposition

Biological location:

Biofluid and excreta:

Blood

Source:

Endogenous

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	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3-Hydroxyquinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-2901000000-46662034299736c6d91a	Spectrum
Predicted GC-MS	3-Hydroxyquinine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03k9-4192400000-35f213d793369e0c6fa1	Spectrum
Predicted GC-MS	3-Hydroxyquinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Hydroxyquinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-757d948be08bc83ac896	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0409000000-0750a9802133c3ad7e0f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-0911000000-f7b63c5080fbb178b639	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c895e6c74087aa4b7c23	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dr-0119000000-8ff71092af9c3960da8e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uk9-0911000000-a23d26a2164f67414c08	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-6eb038badadf80b7dada	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000b-0489000000-9bb3e6ff8d6f7f01ae22	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fr-0901000000-5fd6aa84f8079b3fc2d8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-3b43e0643b1819424eeb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-9364abb1565c929aab29	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00li-0961000000-7bb8ff583560fe8cdfb7	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

138373

ChEMBL ID

Not Available

KEGG Compound ID

C07344

Pubchem Compound ID

441264

Pubchem Substance ID

Not Available

ChEBI ID

17685

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01091

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

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

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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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

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 3-Hydroxyquinine (FDB022421)

Structure for FDB022421 (3-Hydroxyquinine)