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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:30 UTC
Update Date2019-07-23 07:14:23 UTC
HMDB IDHMDB0060462
Secondary Accession Numbers
  • HMDB60462
Metabolite Identification
Common NameCitalopram aldehyde
DescriptionCitalopram aldehyde belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Citalopram aldehyde is a metabolite of citalopram. Citalopram aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Citalopram aldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, citalopram aldehyde participates in a number of enzymatic reactions. In particular, citalopram aldehyde and dimethylamine can be biosynthesized from citalopram; which is catalyzed by the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In addition, citalopram aldehyde and methylammonium can be biosynthesized from N-desmethylcitalopram through the action of the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In humans, citalopram aldehyde 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?1563866063
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
Description belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassNot Available
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frj-6790000000-5810e3f0b2e8639294b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0090000000-5ead17bd5375dba4f0d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-3190000000-858185335b33b264bbcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9640000000-5db7455bc924c50e4db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-4c8f04a15eeec4d1438dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-fc12c3574f53fe0865a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9150000000-63b05d99317987b187a6Spectrum
Biological Properties
Cellular Locations
  • 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 IDC16612
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9944000
PDB IDNot Available
ChEBI ID80607
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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