4-{[(3S,4R)-4-(4-fluorophenyl)piperidin-3-yl]methoxy}benzene-1,2-diol hydrochloride

• ChemBase ID: 166442
• Molecular Formular: C18H21ClFNO3
• Molecular Mass: 353.8156432
• Monoisotopic Mass: 353.11939944
• SMILES: C1NC[C@H]([C@@H](C1)c1ccc(cc1)F)COc1ccc(c(c1)O)O.Cl
• Canonical SMILES: Fc1ccc(cc1)[C@@H]1CCNC[C@H]1COc1ccc(c(c1)O)O.Cl
• InChI: InChI=1S/C18H20FNO3.ClH/c19-14-3-1-12(2-4-14)16-7-8-20-10-13(16)11-23-15-5-6-17(21)18(22)9-15;/h1-6,9,13,16,20-22H,7-8,10-11H2;1H/t13-,16-;/m0./s1
• InChIKey: GIPUDSSHAJOHQK-LINSIKMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(3S,4R)-4-(4-fluorophenyl)piperidin-3-yl]methoxy}benzene-1,2-diol hydrochloride
• IUPAC Traditional name: 4-{[(3S,4R)-4-(4-fluorophenyl)piperidin-3-yl]methoxy}benzene-1,2-diol hydrochloride
• Synonyms: 4-[[(3S,4R)-4-(4-Fluorophenyl)-3-piperidinyl]methoxy]-1,2-benzenediol Hydrochloride; (3S-trans)-4-[[4-(4-Fluorophenyl)-3-piperidinyl]methoxy]-1,2-benzenediol Hydrochloride; BRL 36610; Paroxetine catechol; Desmethylene Paroxetine Hydrochloride Salt

Database IDs

• CAS Number: 159126-30-4
• PubChem SID: 162260575
• PubChem CID: 71315739

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.6535289
• Log P: 2.1132154
• Molar Refractivity: 86.2186 cm^3
• Polarizability: 33.241344 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 9.934216
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.27942443

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid
• Melting Point: 104-107°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291645

A major metabolite of the antidepressant Paroxetine (P205750).

REFERENCES

• Segura, M., et al.: Bioorg. Chem., 31, 248 (2003)
• Wei, P., et al.: Bioorg. Med. Chem. Lett., 14, 3093 (2003)