Citalopram propionic acid (CHEM022576)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:40:04 UTC
Update Date2016-11-09 01:17:32 UTC
Accession NumberCHEM022576
Identification
Common NameCitalopram propionic acid
ClassSmall Molecule
DescriptionCitalopram propionic acid 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)
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Citalopram propionateGenerator
Chemical FormulaC18H14FNO3
Average Molecular Mass311.307 g/mol
Monoisotopic Mass311.096 g/mol
CAS Registry NumberNot Available
IUPAC Name3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid
Traditional Namecitalopram propionic acid
SMILESOC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP2.88ALOGPS
logP3.17ChemAxon
logS-4.8ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0190000000-3d06e9999ac297d7ff75Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-2190000000-85bbf7d086d9c3730e81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0097000000-a4cc60c1a67d15d9c509Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u3-0191000000-32bf56429ae77a046a9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3690000000-f1889e924027df9a1682Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0039000000-205792dd03a321acfceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1097000000-57e6d8b00468c04d0b19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-3190000000-9d9fff6b255b7514f399Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0049000000-a7d194ab1cdb94ae9a7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xu-0092000000-8cefa8ea29df30a2f797Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0960000000-6fc219207c652c40f484Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0096000000-d242411d68accb5c784dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-1fa7dadbab9070f3b687Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1390000000-5075c17d729f9b4abae4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060463
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID80605
PubChem Compound ID10403174
Kegg Compound IDC16610
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.