Showing Compound Cinchonidine (FDB002116)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2020-02-24 19:10:25 UTC

Primary ID

FDB002116

Secondary Accession Numbers

FDB002117

Chemical Information

FooDB Name

Cinchonidine

Description

Cinchonidine 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. Cinchonidine has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and olives (Olea europaea). This could make cinchonidine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinchonidine.

CAS Number

485-71-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Cinchonine, hexaiodotl(-2) (1:1), (9S)-isomer	MeSH
Cinchonine, hydrochloride, (9S)-isomer	MeSH
Cinchonine, monohydrochloride, (9S)-isomer	MeSH
Cinchonine, sulfate (2:1), (9S)-isomer	MeSH
(-)-Cinchonidine	HMDB
(8a,9R)-Cinchonan-9-ol, 9ci	HMDB
(8alpha ,9R)-Cinchonan-9-ol	HMDB
(8S,9R)-Cinchonidine	HMDB
a-Quinidine	HMDB
alpha -Quinidine	HMDB
alpha-Quinidine	HMDB
Cinchovatine	HMDB
L-Cinchonidine	HMDB
Nchem.180-comp1b	HMDB
Cinchonidine monohydrochloride	MeSH, HMDB
Cinchonidine sulfate(2:1)	MeSH, HMDB
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer	MeSH, HMDB
Cinchonidine hydrochloride	MeSH, HMDB
Cinchonidine	MeSH
(-)-cinchonidine	biospider
(8α,9R)-Cinchonan-9-ol	biospider
(8a,9R)-Cinchonan-9-ol, 9CI	db_source
α-quinidine	biospider
Alpha-quinidine	biospider
Cinchonan-9-ol, (8α, 9R)-	biospider
Cinchonan-9-ol, (8α,9R)-	biospider
L-cinchonidine	biospider
nchem.180-comp1b	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.67	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.23 m³·mol⁻¹	ChemAxon
Polarizability	33.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H22N2O

IUPAC name

{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol

InChI Identifier

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2

InChI Key

KMPWYEUPVWOPIM-UHFFFAOYSA-N

Isomeric SMILES

OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2

Average Molecular Weight

294.3908

Monoisotopic Molecular Weight

294.173213336

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
Quinuclidine
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.52%; H 7.53%; N 9.52%; O 5.43%	DFC
Melting Point	Mp 210.5° (205°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.2 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.82	SANGSTER (1994)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -110 (EtOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a5i-2910000000-0f0ed0cb19d7fe7fadca	Spectrum
Predicted GC-MS	Cinchonidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00a9-9875000000-eaf01aacdc509130f140	Spectrum
Predicted GC-MS	Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0002-0960000000-6456c6c3bb2715a7fa00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0960000000-6456c6c3bb2715a7fa00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-6187f815acdbbec47fb2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00lu-2900000000-14f3c34cde5aa2a11079	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00nb-2940000000-eb3a248cf968cf941040	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-069v-0980000000-48c213347c975179636c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-0090000000-0e970cbc2afa57a9654f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-858bee716ec1d75adc07	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0561-1940000000-26e7e3cbae5ea5fb610f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-b480b5a0b696f940452f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-f93b51b0818b008b49b7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00lr-1900000000-603d73783b786d42fdc1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-6595d19fdd23a9e3238b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-5a94ad8c559d5c375bdd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-c81a1076dcd69ebccce3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0090000000-ae336d292aca65dcc174	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0090000000-166d01b77083c7e27751	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-001j-2950000000-88afa86bed375ec3a70c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-0190000000-6abca9144bc157cadb34	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0090000000-ad4802f48f7823037200	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-0890000000-dfa80dddb949e8796af0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ac9-0910000000-23c8a136dc8bfb4979ca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0190000000-49f8db7ac84bad0edd86	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002f-0290000000-9d17bd1a54e6ff3cde9b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057r-1910000000-835c9a14cf1712dd341b	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C11379

Pubchem Compound ID

101744

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CFP80-X:CFP80-X

EAFUS ID

Not Available

Dr. Duke ID

CINCHONIDINE

BIGG ID

Not Available

KNApSAcK ID

C00002147

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

Cinchonidine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti flu	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE