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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-18 17:42:26 UTC
Update Date2021-09-14 15:47:40 UTC
HMDB IDHMDB0060654
Secondary Accession Numbers
  • HMDB60654
Metabolite Identification
Common NameCitalopram N-oxide
DescriptionCitalopram N-oxide belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Citalopram N-oxide is a metabolite of citalopram. Citalopram N-oxide is a strong basic compound (based on its pKa). citalopram N-oxide can be biosynthesized from citalopram; which is mediated by the enzyme cytochrome P450 2D6. In humans, citalopram N-oxide is involved in citalopram metabolism pathway. It has U.S. Food and Drug Administration (FDA) approval to treat major depression, and is prescribed off-label for a number of anxiety conditions.
Structure
Data?1563866087
SynonymsNot Available
Chemical FormulaC20H21FN2O2
Average Molecular Weight340.3913
Monoisotopic Molecular Weight340.158706131
IUPAC Name3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropanamine oxide
Traditional Namecitalopram N-oxide
CAS Registry NumberNot Available
SMILES
CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C20H21FN2O2/c1-23(2,24)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-25-20/h4-9,12H,3,10-11,14H2,1-2H3
InChI KeyDIOGFDCEWUUSBQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Trialkyl amine oxide
  • N-oxide
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Trisubstituted n-oxide
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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
Water Solubility0.002 g/LALOGPS
logP10(1.2) g/LALOGPS
logP10(2.64) g/LChemAxon
logS10(-5.2) g/LALOGPS
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.07 m³·mol⁻¹ChemAxon
Polarizability36.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+181.31630932474
DeepCCS[M-H]-178.95830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citalopram N-oxideCN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C13679.1Standard polar33892256
Citalopram N-oxideCN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C12422.7Standard non polar33892256
Citalopram N-oxideCN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C12468.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1191000000-61350a6a4e7c7ec574612017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram N-oxide 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 - Citalopram N-oxide 10V, Positive-QTOFsplash10-0006-0029000000-44d92e428209f50b8f522017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram N-oxide 20V, Positive-QTOFsplash10-001c-4397000000-1ca72d34b2e820c2e98a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram N-oxide 40V, Positive-QTOFsplash10-00s9-8960000000-f90431365d18605158e62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram N-oxide 10V, Negative-QTOFsplash10-000i-0009000000-4fec0d54847fd5c5d7cc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram N-oxide 20V, Negative-QTOFsplash10-000i-1019000000-19ea08ed4fbf629707542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram N-oxide 40V, Negative-QTOFsplash10-000j-4190000000-328d5f705437721a32ee2017-10-06Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
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 IDNot Available
KEGG Compound IDC16607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10068142
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 ReferencesNot Available