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Record Information
Version3.6
Creation Date2013-06-18 17:42:26 UTC
Update Date2016-02-11 08:10:17 UTC
HMDB IDHMDB60654
Secondary Accession NumbersNone
Metabolite Identification
Common NameCitalopram N-oxide
DescriptionCitalopram N-oxide is a metabolite of citalopram. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. 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. (Wikipedia)
Structure
Thumb
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=1/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 KeyInChIKey=DIOGFDCEWUUSBQ-UHFFFAOYNA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.002 mg/mLALOGPS
logP1.2ALOGPS
logP2.64ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.9 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.07 m3·mol-1ChemAxon
Polarizability36.04 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00195
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16607
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60654
Metagene LinkHMDB60654
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available