Showing metabocard for 3-Hydroxyquinine (BMDB0001091)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:00 UTC
Update Date2020-04-22 15:06:40 UTC
BMDB IDBMDB0001091
Secondary Accession Numbers
  • BMDB01091
Metabolite Identification
Common Name3-Hydroxyquinine
Description3-Hydroxyquinine 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. Based on a literature review a significant number of articles have been published on 3-Hydroxyquinine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-HydroxyquinidineHMDB, MeSH
6'-Methoxycinchonan-3,9-diolHMDB
3-Hydroxyquinidine, (3alpha,9S)-isomerMeSH, HMDB
3-Hydroxyquinidine, (8alpha,9R)-isomerMeSH, HMDB
3-HydroxyquinineMeSH
Chemical FormulaC20H24N2O3
Average Molecular Weight340.4162
Monoisotopic Molecular Weight340.178692644
IUPAC Name(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol
Traditional Name3-hydroxyquinidine
CAS Registry Number53467-23-5
SMILES
[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12
InChI Identifier
InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1
InChI KeyBSRUJCFCZKMFMB-ZNYHDOEXSA-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
  • Anisole
  • Quinuclidine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic alcohol
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.24ALOGPS
logP1.67ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)13.55ChemAxon
pKa (Strongest Basic)8.63ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.91 m³·mol⁻¹ChemAxon
Polarizability36.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2901000000-46662034299736c6d91aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-4192400000-35f213d793369e0c6fa1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-757d948be08bc83ac896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0409000000-0750a9802133c3ad7e0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0911000000-f7b63c5080fbb178b639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c895e6c74087aa4b7c23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0119000000-8ff71092af9c3960da8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-0911000000-a23d26a2164f67414c08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-6eb038badadf80b7dadaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0489000000-9bb3e6ff8d6f7f01ae22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-0901000000-5fd6aa84f8079b3fc2d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-3b43e0643b1819424eebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-9364abb1565c929aab29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-0961000000-7bb8ff583560fe8cdfb7View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001091
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022421
KNApSAcK IDNot Available
Chemspider ID138373
KEGG Compound IDC07344
BioCyc ID3-HYDROXYQUININE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2234
PubChem Compound441264
PDB IDNot Available
ChEBI ID17685
References
Synthesis ReferenceCarroll, F. Ivy; Abraham, Philip; Gaetano, Kevan; Mascarella, S. Wayne; Wohl, Ronald A.; Lind, Joan; Petzoldt, Karl. (3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate. J. Chem. Soc., Perkin Trans. 1, 1991, 12, 3017-3026
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available