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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:40:50 UTC
Update Date2022-03-07 03:18:14 UTC
HMDB IDHMDB0240236
Secondary Accession NumbersNone
Metabolite Identification
Common NameQuifenadine
DescriptionQuifenadine belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. In humans, quifenadine is involved in the quifenadine h1-antihistamine action pathway. Quifenadine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Quifenadine.
Structure
Data?1563892734
Synonyms
ValueSource
Α,α-diphenyl-3-quinuclidinemethanolHMDB
alpha,alpha-Diphenyl-3-quinuclidinemethanolHMDB
Diphenyl-3-quinuclidylcarbinolHMDB
QuifenadineHMDB
Chemical FormulaC20H23NO
Average Molecular Weight293.41
Monoisotopic Molecular Weight293.177964365
IUPAC Name{1-azabicyclo[2.2.2]octan-2-yl}diphenylmethanol
Traditional Name1-azabicyclo[2.2.2]octan-2-yldiphenylmethanol
CAS Registry Number10447-39-9
SMILES
OC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C20H23NO/c22-20(17-7-3-1-4-8-17,18-9-5-2-6-10-18)19-15-16-11-13-21(19)14-12-16/h1-10,16,19,22H,11-15H2
InChI KeyJNZMANQLHCNXTA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Quinuclidine
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Azacycle
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
RoleNot Available
Physical Properties
StateNot Available
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
logP3.77ALOGPS
logP3.52ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)9.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.9 m³·mol⁻¹ChemAxon
Polarizability33.29 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
AllCCS[M-H]-179.40531661259
AllCCS[M+H]+172.10531661259
DeepCCS[M+H]+165.92630932474
DeepCCS[M-H]-163.56830932474
DeepCCS[M-2H]-196.45430932474
DeepCCS[M+Na]+172.01930932474
AllCCS[M+H]+172.132859911
AllCCS[M+H-H2O]+168.632859911
AllCCS[M+NH4]+175.332859911
AllCCS[M+Na]+176.332859911
AllCCS[M-H]-179.432859911
AllCCS[M+Na-2H]-179.032859911
AllCCS[M+HCOO]-178.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
QuifenadineOC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C12791.3Standard polar33892256
QuifenadineOC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C12297.7Standard non polar33892256
QuifenadineOC(C1CC2CCN1CC2)(C1=CC=CC=C1)C1=CC=CC=C12361.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Quifenadine,1TMS,isomer #1C[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CC2CCN1CC22432.9Semi standard non polar33892256
Quifenadine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C1=CC=CC=C1)(C1=CC=CC=C1)C1CC2CCN1CC22669.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Quifenadine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quifenadine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quifenadine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quifenadine GC-MS ("Quifenadine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 10V, Positive-QTOFsplash10-0006-0190000000-256fa29ee83a48fb7eeb2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 20V, Positive-QTOFsplash10-0036-0980000000-b7e02cfd3848711fd4152019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 40V, Positive-QTOFsplash10-08fr-3900000000-6776e6b0e1ea3161e72c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 10V, Negative-QTOFsplash10-0006-0090000000-0ae6164e56a923d4a3482019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 20V, Negative-QTOFsplash10-0006-1190000000-683090136635d8db9f232019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 40V, Negative-QTOFsplash10-08i0-4930000000-bb3852505004a55484e52019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 10V, Negative-QTOFsplash10-0006-0090000000-17a2775e8d18d2b59e532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 20V, Negative-QTOFsplash10-0006-0490000000-b01fba61a2444ab31cb12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 40V, Negative-QTOFsplash10-0a4i-0940000000-c0b9e9dfa089487f14a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 10V, Positive-QTOFsplash10-0006-0090000000-235438a9e84c804828842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 20V, Positive-QTOFsplash10-0006-0190000000-6bb1a66dbb898613e4cd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quifenadine 40V, Positive-QTOFsplash10-03di-0900000000-7c4da14f6ad13d15d47d2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2308316
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuifenadine
METLIN IDNot Available
PubChem Compound3045613
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. Makarov L, Balykova L, Soldatova O, Komolyatova V, Serebruany V: The antiarrhythmic properties of quifenadine, H1-histamine receptor blocker in children with premature beats: a randomized controlled pilot trial. Am J Ther. 2010 Jul-Aug;17(4):396-401. doi: 10.1097/MJT.0b013e3181a86987. [PubMed:19487925 ]