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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:30 UTC
Update Date2021-09-14 15:47:54 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

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 Solubility0.0044 g/LALOGPS
logP10(3.05) g/LALOGPS
logP10(3.01) g/LChemAxon
logS10(-4.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.26230932474
DeepCCS[M-H]-163.90430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citalopram aldehydeFC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N3499.8Standard polar33892256
Citalopram aldehydeFC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N2368.1Standard non polar33892256
Citalopram aldehydeFC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N2357.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citalopram aldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212521.5Semi standard non polar33892256
Citalopram aldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212432.8Standard non polar33892256
Citalopram aldehyde,1TMS,isomer #1C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C213124.3Standard polar33892256
Citalopram aldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212770.0Semi standard non polar33892256
Citalopram aldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212642.0Standard non polar33892256
Citalopram aldehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C213224.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram aldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0frj-6790000000-5810e3f0b2e8639294b82017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram aldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram aldehyde 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 aldehyde 10V, Positive-QTOFsplash10-002b-0090000000-5ead17bd5375dba4f0d72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 20V, Positive-QTOFsplash10-004l-3190000000-858185335b33b264bbca2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 40V, Positive-QTOFsplash10-0fr6-9640000000-5db7455bc924c50e4db32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 10V, Negative-QTOFsplash10-0006-0090000000-4c8f04a15eeec4d1438d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 20V, Negative-QTOFsplash10-0006-0090000000-fc12c3574f53fe0865a22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 40V, Negative-QTOFsplash10-0006-9150000000-63b05d99317987b187a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 10V, Positive-QTOFsplash10-0002-0090000000-7111d74cac5fc00f8d152021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 20V, Positive-QTOFsplash10-014j-0290000000-9366990781f41be3c9f52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 40V, Positive-QTOFsplash10-0609-1940000000-82fe51aefa8f4cbb5b932021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 10V, Negative-QTOFsplash10-0006-0090000000-457637be3c95254ed61e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 20V, Negative-QTOFsplash10-0f79-0190000000-4d7069168725469b18c62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram aldehyde 40V, Negative-QTOFsplash10-0udr-3980000000-516fbc25e612fe1f12fb2021-10-12Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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