Cinchonidine (CHEM024307)

Record Information
Version1.0
Creation Date2016-05-25 21:37:25 UTC
Update Date2026-08-20 03:21:52 UTC
Accession NumberCHEM024307
Identification
Common NameCinchonidine
ClassSmall Molecule
Description
Alkaloid from the leaves of Olea europaea Cinchonidine is an alkaloid used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonine. Cinchonidine is found in olive, herbs and spices, and fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC19H22N2O
Average Molecular Mass294.391 g/mol
Monoisotopic Mass294.173 g/mol
CAS Registry Number485-71-2
IUPAC Name{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol
Traditional Namecinchonidine sulfate
SMILESOC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0250260
FooDB IDFDB002116
Phenol Explorer IDNot Available
KNApSAcK IDC00002147
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCinchonidine
Chemspider ID2655
ChEBI IDNot Available
PubChem Compound ID2757
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References