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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:52 UTC
HMDB IDHMDB0001091
Secondary Accession Numbers
  • HMDB01091
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. 3-Hydroxyquinine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-hydroxyquinine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Hydroxyquinine.
Structure
Data?1582752176
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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.58731661259
DarkChem[M-H]-176.45731661259
AllCCS[M+H]+184.06532859911
AllCCS[M-H]-188.25232859911
DeepCCS[M-2H]-214.90930932474
DeepCCS[M+Na]+190.15830932474
AllCCS[M+H]+184.132859911
AllCCS[M+H-H2O]+180.932859911
AllCCS[M+NH4]+186.932859911
AllCCS[M+Na]+187.832859911
AllCCS[M-H]-188.332859911
AllCCS[M+Na-2H]-188.432859911
AllCCS[M+HCOO]-188.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxyquinine[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C123504.6Standard polar33892256
3-Hydroxyquinine[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C122834.8Standard non polar33892256
3-Hydroxyquinine[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C123068.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyquinine,1TMS,isomer #1C=C[C@@]1(O[Si](C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C122746.2Semi standard non polar33892256
3-Hydroxyquinine,1TMS,isomer #2C=C[C@@]1(O)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C)C1=CC=NC2=CC=C(OC)C=C122773.5Semi standard non polar33892256
3-Hydroxyquinine,2TMS,isomer #1C=C[C@@]1(O[Si](C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C)C1=CC=NC2=CC=C(OC)C=C122775.4Semi standard non polar33892256
3-Hydroxyquinine,1TBDMS,isomer #1C=C[C@@]1(O[Si](C)(C)C(C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C122999.1Semi standard non polar33892256
3-Hydroxyquinine,1TBDMS,isomer #2C=C[C@@]1(O)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(OC)C=C123024.9Semi standard non polar33892256
3-Hydroxyquinine,2TBDMS,isomer #1C=C[C@@]1(O[Si](C)(C)C(C)(C)C)CN2CC[C@@H]1C[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(OC)C=C123262.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2901000000-46662034299736c6d91a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-4192400000-35f213d793369e0c6fa12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyquinine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Positive-QTOFsplash10-00di-0009000000-757d948be08bc83ac8962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Positive-QTOFsplash10-0ab9-0409000000-0750a9802133c3ad7e0f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Positive-QTOFsplash10-053r-0911000000-f7b63c5080fbb178b6392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Negative-QTOFsplash10-000i-0009000000-c895e6c74087aa4b7c232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Negative-QTOFsplash10-00dr-0119000000-8ff71092af9c3960da8e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Negative-QTOFsplash10-0uk9-0911000000-a23d26a2164f67414c082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Negative-QTOFsplash10-000i-0009000000-6eb038badadf80b7dada2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Negative-QTOFsplash10-000b-0489000000-9bb3e6ff8d6f7f01ae222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Negative-QTOFsplash10-08fr-0901000000-5fd6aa84f8079b3fc2d82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 10V, Positive-QTOFsplash10-0006-0009000000-3b43e0643b1819424eeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 20V, Positive-QTOFsplash10-0006-0009000000-9364abb1565c929aab292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyquinine 40V, Positive-QTOFsplash10-00li-0961000000-7bb8ff583560fe8cdfb72021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.52 (2.35-4.40) uMAdult (>18 years old)Both
Malaria
details
BloodDetected and Quantified2.90 (1.76-6.16) uMAdult (>18 years old)Both
Malaria
details
Associated Disorders and Diseases
Disease References
Malaria
  1. Pukrittayakamee S, Pitisuttithum P, Zhang H, Jantra A, Wanwimolruk S, White NJ: Effects of cigarette smoking on quinine pharmacokinetics in malaria. Eur J Clin Pharmacol. 2002 Aug;58(5):315-9. Epub 2002 Jun 20. [PubMed:12185554 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 References
  1. 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. [PubMed:3627599 ]
  2. 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. [PubMed:14576102 ]
  3. 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. [PubMed:10976551 ]
  4. 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. [PubMed:15896247 ]
  5. 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. [PubMed:12811361 ]
  6. 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. [PubMed:10579472 ]
  7. 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. [PubMed:12957180 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Reactions
Quinine + NADPH + Oxygen → 3-Hydroxyquinine + NADP + Waterdetails