3-Hydroxyquinine (CHEM035072)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:28:11 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035072
Identification
Common Name3-Hydroxyquinine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass340.416 g/mol
Monoisotopic Mass340.179 g/mol
CAS Registry Number53467-23-5
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
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 IdentifierInChI=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
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 Solubility1.14 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2901000000-46662034299736c6d91aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-4192400000-35f213d793369e0c6fa1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-757d948be08bc83ac896Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0409000000-0750a9802133c3ad7e0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0911000000-f7b63c5080fbb178b639Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c895e6c74087aa4b7c23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0119000000-8ff71092af9c3960da8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-0911000000-a23d26a2164f67414c08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-6eb038badadf80b7dadaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0489000000-9bb3e6ff8d6f7f01ae22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-0901000000-5fd6aa84f8079b3fc2d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-3b43e0643b1819424eebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-9364abb1565c929aab29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-0961000000-7bb8ff583560fe8cdfb7Spectrum
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
DrugBank IDNot Available
HMDB IDHMDB0001091
FooDB IDFDB022421
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID3-HYDROXYQUININE
METLIN ID2234
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID138373
ChEBI ID17685
PubChem Compound ID441264
Kegg Compound IDC07344
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Carroll, 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
2. Killeen AA, Bowers LD: Fetal supraventricular tachycardia treated with high-dose quinidine: toxicity associated with marked elevation of the metabolite, 3(S)-3-hydroxyquinidine. Obstet Gynecol. 1987 Sep;70(3 Pt 2):445-9.
3. Pukrittayakamee S, Wanwimolruk S, Stepniewska K, Jantra A, Huyakorn S, Looareesuwan S, White NJ: Quinine pharmacokinetic-pharmacodynamic relationships in uncomplicated falciparum malaria. Antimicrob Agents Chemother. 2003 Nov;47(11):3458-63.
4. Damkier P, Brosen K: Quinidine as a probe for CYP3A4 activity: intrasubject variability and lack of correlation with probe-based assays for CYP1A2, CYP2C9, CYP2C19, and CYP2D6. Clin Pharmacol Ther. 2000 Aug;68(2):199-209.
5. Ridtitid W, Wongnawa M, Mahatthanatrakul W, Raungsri N, Sunbhanich M: Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers. J Clin Pharm Ther. 2005 Jun;30(3):285-90.
6. Christensen M, Andersson K, Dalen P, Mirghani RA, Muirhead GJ, Nordmark A, Tybring G, Wahlberg A, Yasar U, Bertilsson L: The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes. Clin Pharmacol Ther. 2003 Jun;73(6):517-28.
7. Mirghani RA, Hellgren U, Westerberg PA, Ericsson O, Bertilsson L, Gustafsson LL: The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo. Clin Pharmacol Ther. 1999 Nov;66(5):454-60.
8. Jansson A, Gustafsson LL, Mirghani RA: High-performance liquid chromatographic method for the determination of quinine and 3-hydroxyquinine in blood samples dried on filter paper. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Sep 25;795(1):151-6.