3-[(1S)-5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid

• ChemBase ID: 167195
• Molecular Formular: C18H14FNO3
• Molecular Mass: 311.3070632
• Monoisotopic Mass: 311.09577153
• SMILES: c1(ccc2c(c1)CO[C@]2(c1ccc(cc1)F)CCC(=O)O)C#N
• Canonical SMILES: N#Cc1ccc2c(c1)CO[C@@]2(CCC(=O)O)c1ccc(cc1)F
• InChI: 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)/t18-/m0/s1
• InChIKey: JSYNRZJODZWUKX-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1S)-5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid
• IUPAC Traditional name: 3-[(1S)-5-cyano-1-(4-fluorophenyl)-3H-2-benzofuran-1-yl]propanoic acid
• Synonyms: (1S)-5-Cyano-1-(4-fluorophenyl)-1,3-dihydro-1-isobenzofuranpropanoic Acid; (S)-3-[5-Cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl]propionic Acid; (S)-Didemethylamino Citalopram Carboxylic Acid

Database IDs

• CAS Number: 766508-94-5
• PubChem SID: 162261328
• PubChem CID: 11312947

CALCULATED PROPERTIES

• Acid pKa: 3.641667
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3168483
• LogD (pH = 7.4): -0.15604684
• Log P: 3.1719944
• Molar Refractivity: 82.0301 cm^3
• Polarizability: 31.105448 Å^3
• Polar Surface Area: 70.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D439440

A metabolite of Citalopram (C505000).

REFERENCES

• Bertilsson, L., et al.: Eur. J. Clin. Pharmacol., 18, 483 (1980)
• Rochat, B., et al.: Brain Res., 831, 229 (1980)
• Bertilsson, L., et al.: Pharmacol. Toxicol., 68, 100 (1980)