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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:35:54 UTC
Update Date2022-09-22 18:34:24 UTC
HMDB IDHMDB0030282
Secondary Accession Numbers
  • HMDB30282
Metabolite Identification
Common 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.
Structure
Data?1563861964
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 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
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 mg/mL at 25 °CNot Available
LogP2.82Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.89431661259
DarkChem[M-H]-167.5931661259
DeepCCS[M+H]+163.7130932474
DeepCCS[M-H]-161.35230932474
DeepCCS[M-2H]-194.23830932474
DeepCCS[M+Na]+169.80330932474
AllCCS[M+H]+174.032859911
AllCCS[M+H-H2O]+170.432859911
AllCCS[M+NH4]+177.232859911
AllCCS[M+Na]+178.232859911
AllCCS[M-H]-180.232859911
AllCCS[M+Na-2H]-180.032859911
AllCCS[M+HCOO]-179.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CinchonidineOC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C23281.7Standard polar33892256
CinchonidineOC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C22548.2Standard non polar33892256
CinchonidineOC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C22597.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cinchonidine,1TMS,isomer #1C=CC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=CC=C122509.7Semi standard non polar33892256
Cinchonidine,1TBDMS,isomer #1C=CC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=CC=C122725.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-2910000000-0f0ed0cb19d7fe7fadca2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinchonidine GC-MS (1 TMS) - 70eV, Positivesplash10-00a9-9875000000-eaf01aacdc509130f1402017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine LC-ESI-qTof , Positive-QTOFsplash10-0002-0960000000-6456c6c3bb2715a7fa002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine , positive-QTOFsplash10-0002-0960000000-6456c6c3bb2715a7fa002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 20V, Positive-QTOFsplash10-0002-0090000000-6187f815acdbbec47fb22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-00lu-2900000000-14f3c34cde5aa2a110792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-00nb-2940000000-eb3a248cf968cf9410402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 30V, Positive-QTOFsplash10-069v-0980000000-48c213347c975179636c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 15V, Positive-QTOFsplash10-0002-0090000000-0e970cbc2afa57a9654f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-858bee716ec1d75adc072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0561-1940000000-26e7e3cbae5ea5fb610f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 10V, Positive-QTOFsplash10-0002-0090000000-b480b5a0b696f940452f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-f93b51b0818b008b49b72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-00lr-1900000000-603d73783b786d42fdc12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-6595d19fdd23a9e3238b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-5a94ad8c559d5c375bdd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-c81a1076dcd69ebccce32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0090000000-ae336d292aca65dcc1742021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0090000000-166d01b77083c7e277512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-001j-2950000000-88afa86bed375ec3a70c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOFsplash10-0002-0190000000-6abca9144bc157cadb342021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 10V, Positive-QTOFsplash10-004j-0090000000-ad4802f48f78230372002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 20V, Positive-QTOFsplash10-004r-0890000000-dfa80dddb949e8796af02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 40V, Positive-QTOFsplash10-0ac9-0910000000-23c8a136dc8bfb4979ca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 10V, Negative-QTOFsplash10-0006-0190000000-49f8db7ac84bad0edd862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 20V, Negative-QTOFsplash10-002f-0290000000-9d17bd1a54e6ff3cde9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cinchonidine 40V, Negative-QTOFsplash10-057r-1910000000-835c9a14cf1712dd341b2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002116
KNApSAcK IDC00002147
Chemspider ID2655
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinchonidine
METLIN IDNot Available
PubChem Compound2757
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .