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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:54 UTC
Update Date2019-01-11 19:39:58 UTC
HMDB IDHMDB0030282
Secondary Accession Numbers
  • HMDB30282
Metabolite Identification
Common NameCinchonidine
DescriptionCinchonine is found in fruits. Cinchonine is an alkaloid from the leaves of Olea europaea Cinchonine is an alkaloidwith molecular formula C19H22N2O used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine
Structure
Data?1547235598
Synonyms
ValueSource
(-)-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
Cinchonidine sulfate(2:1)MeSH
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomerMeSH
Chemical FormulaC19H22N2O
Average Molecular Weight294.3908
Monoisotopic Molecular Weight294.173213336
IUPAC Name{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol
Traditional Namecinchonidine sulfate
CAS Registry Number485-71-2
SMILES
OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2
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 KeyKMPWYEUPVWOPIM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point210.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 25 °CNot Available
LogP2.82Not Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-2910000000-0f0ed0cb19d7fe7fadcaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00a9-9875000000-eaf01aacdc509130f140View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0960000000-6456c6c3bb2715a7fa00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0960000000-6456c6c3bb2715a7fa00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0090000000-ad4802f48f7823037200View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0890000000-dfa80dddb949e8796af0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac9-0910000000-23c8a136dc8bfb4979caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-49f8db7ac84bad0edd86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0290000000-9d17bd1a54e6ff3cde9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057r-1910000000-835c9a14cf1712dd341bView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002116
KNApSAcK IDNot Available
Chemspider ID2655
KEGG Compound IDC11379
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinchonidine
METLIN IDNot Available
PubChem Compound2757
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shah BH, Nawaz Z, Virani SS, Ali IQ, Saeed SA, Gilani AH: The inhibitory effect of cinchonine on human platelet aggregation due to blockade of calcium influx. Biochem Pharmacol. 1998 Oct 15;56(8):955-60. [PubMed:9776305 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .