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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:30 UTC
Update Date2017-10-23 19:15:43 UTC
HMDB IDHMDB0060462
Secondary Accession Numbers
  • HMDB60462
Metabolite Identification
Common NameCitalopram aldehyde
DescriptionCitalopram aldehyde 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 FormulaC18H14FNO2
Average Molecular Weight295.3077
Monoisotopic Molecular Weight295.100856902
IUPAC Name1-(4-fluorophenyl)-1-(3-oxopropyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional Namecitalopram aldehyde
CAS Registry NumberNot Available
SMILES
FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N
InChI Identifier
InChI=1S/C18H14FNO2/c19-16-5-3-15(4-6-16)18(8-1-9-21)17-7-2-13(11-20)10-14(17)12-22-18/h2-7,9-10H,1,8,12H2
InChI KeyBBYAFETUIKMLSF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as isocoumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIsocoumarans
Direct ParentIsocoumarans
Alternative Parents
Substituents
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Alpha-hydrogen aldehyde
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Carbonitrile
  • Nitrile
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aldehyde
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.0044 g/LALOGPS
logP3.05ALOGPS
logP3.01ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)12.93ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.1 m³·mol⁻¹ChemAxon
Polarizability29.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frj-6790000000-5810e3f0b2e8639294b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0090000000-5ead17bd5375dba4f0d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-3190000000-858185335b33b264bbcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9640000000-5db7455bc924c50e4db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-4c8f04a15eeec4d1438dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-fc12c3574f53fe0865a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9150000000-63b05d99317987b187a6View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Citalopram Metabolism PathwayPw000603Pw000603 greyscalePw000603 simpleNot Available
Citalopram PathwayPw000426Pw000426 greyscalePw000426 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16612
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound0
      PDB IDNot Available
      ChEBI ID80607
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Involved in oxidoreductase activity
      Specific function:
      Not Available
      Gene Name:
      AOX1
      Uniprot ID:
      Q06278
      Molecular weight:
      147916.735
      Reactions
      Citalopram aldehyde + Water + Oxygen → Citalopram propionic acid + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
      Gene Name:
      MAOB
      Uniprot ID:
      P27338
      Molecular weight:
      58762.475
      Reactions
      Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxidedetails
      N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxidedetails
      Didemethylcitalopram + Water + Oxygen → Citalopram aldehyde + Ammonia + Hydrogen peroxidedetails
      General function:
      Involved in oxidoreductase activity
      Specific function:
      Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
      Gene Name:
      MAOA
      Uniprot ID:
      P21397
      Molecular weight:
      59681.27
      Reactions
      Citalopram + Oxygen + Water → Citalopram aldehyde + Dimethylamine + Hydrogen peroxidedetails
      N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxidedetails
      Didemethylcitalopram + Water + Oxygen → Citalopram aldehyde + Ammonia + Hydrogen peroxidedetails