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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:34 UTC
Update Date2021-09-14 15:46:31 UTC
HMDB IDHMDB0060463
Secondary Accession Numbers
  • HMDB60463
Metabolite Identification
Common NameCitalopram propionic acid
DescriptionCitalopram propionic acid 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. 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. Citalopram propionic acid is a metabolite of citalopram. Citalopram propionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). citalopram propionic acid can be biosynthesized from citalopram aldehyde through its interaction with the enzyme aldehyde oxidase. In humans, citalopram propionic acid is involved in citalopram metabolism pathway.
Structure
Data?1563866063
Synonyms
ValueSource
Citalopram propionateGenerator
Chemical FormulaC18H14FNO3
Average Molecular Weight311.3071
Monoisotopic Molecular Weight311.095771524
IUPAC Name3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid
Traditional Namecitalopram propionic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C18H14FNO3/c19-15-4-2-14(3-5-15)18(8-7-17(21)22)16-6-1-12(10-20)9-13(16)11-23-18/h1-6,9H,7-8,11H2,(H,21,22)
InChI KeyJSYNRZJODZWUKX-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.0055 g/LALOGPS
logP10(2.88) g/LALOGPS
logP10(3.17) g/LChemAxon
logS10(-4.8) g/LALOGPS
pKa (Strongest Acidic)3.64ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.03 m³·mol⁻¹ChemAxon
Polarizability30.71 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]+174.48930932474
DeepCCS[M-H]-172.13230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citalopram propionic acidOC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C13722.2Standard polar33892256
Citalopram propionic acidOC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C12426.8Standard non polar33892256
Citalopram propionic acidOC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C12563.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citalopram propionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212609.0Semi standard non polar33892256
Citalopram propionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C212870.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram propionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0190000000-3d06e9999ac297d7ff752017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram propionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-000i-2190000000-85bbf7d086d9c3730e812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citalopram propionic acid 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 propionic acid 10V, Positive-QTOFsplash10-03dl-0097000000-a4cc60c1a67d15d9c5092016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Positive-QTOFsplash10-02u3-0191000000-32bf56429ae77a046a9f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Positive-QTOFsplash10-000i-3690000000-f1889e924027df9a16822016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Negative-QTOFsplash10-03di-0039000000-205792dd03a321acfcea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Negative-QTOFsplash10-03di-1097000000-57e6d8b00468c04d0b192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Negative-QTOFsplash10-003b-3190000000-9d9fff6b255b7514f3992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Positive-QTOFsplash10-03dl-0049000000-a7d194ab1cdb94ae9a7a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Positive-QTOFsplash10-03xu-0092000000-8cefa8ea29df30a2f7972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Positive-QTOFsplash10-0a4r-0960000000-6fc219207c652c40f4842021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Negative-QTOFsplash10-03xr-0096000000-d242411d68accb5c784d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Negative-QTOFsplash10-000i-0090000000-1fa7dadbab9070f3b6872021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Negative-QTOFsplash10-000i-1390000000-5075c17d729f9b4abae42021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDC16610
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10403174
PDB IDNot Available
ChEBI ID80605
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