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Showing Compound Cinchonidine (FDB002116)

Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2025-11-18 22:35:01 UTC
Primary IDFDB002116
Secondary Accession Numbers
  • FDB002117
Chemical Information
FooDB NameCinchonidine
DescriptionCinchonidine 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 Number485-71-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Cinchonine, hexaiodotl(-2) (1:1), (9S)-isomerMeSH
Cinchonine, hydrochloride, (9S)-isomerMeSH
Cinchonine, monohydrochloride, (9S)-isomerMeSH
Cinchonine, sulfate (2:1), (9S)-isomerMeSH
(-)-CinchonidineHMDB
(8a,9R)-Cinchonan-9-ol, 9ciHMDB
(8alpha ,9R)-Cinchonan-9-olHMDB
(8S,9R)-CinchonidineHMDB
a-QuinidineHMDB
alpha -QuinidineHMDB
alpha-QuinidineHMDB
CinchovatineHMDB
L-CinchonidineHMDB
Nchem.180-comp1bHMDB
Cinchonidine monohydrochlorideMeSH, HMDB
Cinchonidine sulfate(2:1)MeSH, HMDB
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomerMeSH, HMDB
Cinchonidine hydrochlorideMeSH, HMDB
CinchonidineMeSH
(-)-cinchonidinebiospider
(8α,9R)-Cinchonan-9-olbiospider
(8a,9R)-Cinchonan-9-ol, 9CIdb_source
α-quinidinebiospider
Alpha-quinidinebiospider
Cinchonan-9-ol, (8α, 9R)-biospider
Cinchonan-9-ol, (8α,9R)-biospider
L-cinchonidinebiospider
nchem.180-comp1bbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP3.2ALOGPS
logP2.67ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.88ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.23 m³·mol⁻¹ChemAxon
Polarizability33.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H22N2O
IUPAC name{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol
InChI IdentifierInChI=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 KeyKMPWYEUPVWOPIM-UHFFFAOYSA-N
Isomeric SMILESOC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2
Average Molecular Weight294.3908
Monoisotopic Molecular Weight294.173213336
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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona 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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.52%; H 7.53%; N 9.52%; O 5.43%DFC
Melting PointMp 210.5° (205°)DFC
Boiling PointNot Available
Experimental Water Solubility0.2 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.82SANGSTER (1994)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -110 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a5i-2910000000-0f0ed0cb19d7fe7fadcaSpectrum
Predicted GC-MSCinchonidine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00a9-9875000000-eaf01aacdc509130f140Spectrum
Predicted GC-MSCinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCinchonidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0960000000-6456c6c3bb2715a7fa002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0960000000-6456c6c3bb2715a7fa002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-6187f815acdbbec47fb22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00lu-2900000000-14f3c34cde5aa2a110792021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00nb-2940000000-eb3a248cf968cf9410402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-069v-0980000000-48c213347c975179636c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0090000000-0e970cbc2afa57a9654f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-858bee716ec1d75adc072021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0561-1940000000-26e7e3cbae5ea5fb610f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b480b5a0b696f940452f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-f93b51b0818b008b49b72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00lr-1900000000-603d73783b786d42fdc12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-6595d19fdd23a9e3238b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-5a94ad8c559d5c375bdd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-c81a1076dcd69ebccce32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0090000000-ae336d292aca65dcc1742021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0090000000-166d01b77083c7e277512021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001j-2950000000-88afa86bed375ec3a70c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-0190000000-6abca9144bc157cadb342021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-ad4802f48f78230372002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0890000000-dfa80dddb949e8796af02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac9-0910000000-23c8a136dc8bfb4979ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-49f8db7ac84bad0edd862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0290000000-9d17bd1a54e6ff3cde9b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057r-1910000000-835c9a14cf1712dd341b2016-08-03View Spectrum
NMRNot Available
ChemSpider ID2655
ChEMBL IDCHEMBL15134
KEGG Compound IDC11379
Pubchem Compound ID101744
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0030282
CRC / DFC (Dictionary of Food Compounds) IDCFP80-X:CFP80-X
EAFUS IDNot Available
Dr. Duke IDCINCHONIDINE
BIGG IDNot Available
KNApSAcK IDC00002147
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCinchonidine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).