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Showing Compound Cinchonidine (FDB002116)

Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2020-02-24 19:10:25 UTC
Primary IDFDB002116
Secondary Accession Numbers
  • FDB002117
Chemical Information
FooDB NameCinchonidine
DescriptionCinchonidine, also known as a-quinidine or cinchovatine, 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 is a very strong basic compound (based on its pKa). Cinchonidine has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and olives. This could make cinchonidine a potential biomarker for the consumption of these foods.
CAS Number485-71-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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 monohydrochlorideHMDB
Cinchonidine sulfate(2:1)HMDB
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomerHMDB
Cinchonidine hydrochlorideMeSH
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 - Experimental
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0960000000-6456c6c3bb2715a7fa00Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0960000000-6456c6c3bb2715a7fa00Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-ad4802f48f7823037200Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0890000000-dfa80dddb949e8796af0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac9-0910000000-23c8a136dc8bfb4979caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-49f8db7ac84bad0edd86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0290000000-9d17bd1a54e6ff3cde9bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057r-1910000000-835c9a14cf1712dd341bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC11379
Pubchem Compound ID101744
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
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 A substance that destroys or inhibits replication of viruses.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti pyretic35493 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 viral22587 A substance that destroys or inhibits replication of viruses.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).