2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one

• ChemBase ID: 128101
• Molecular Formular: C22H27NO2
• Molecular Mass: 337.45528
• Monoisotopic Mass: 337.20417911
• SMILES: O=C(c1ccccc1)C[C@@H]1N(C)[C@H](C[C@H](O)c2ccccc2)CCC1
• Canonical SMILES: O[C@H](c1ccccc1)C[C@@H]1CCC[C@@H](N1C)CC(=O)c1ccccc1
• InChI: InChI=1S/C22H27NO2/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18/h2-7,9-12,19-21,24H,8,13-16H2,1H3/t19-,20+,21-/m0/s1
• InChIKey: MXYUKLILVYORSK-HBMCJLEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethan-1-one
• IUPAC Traditional name: (-)-lobeline
• Synonyms: Lobeline

Database IDs

• CAS Number: 90-69-7
• PubChem SID: 162222415
• PubChem CID: 101616
• ATC CODE: QV04CV01
• CHEMBL: 15476
• Chemspider ID: 91814
• KEGG ID: D02364
• Unique Ingredient Identifier: D0P25S3P81
• Wikipedia Title: Lobeline

CALCULATED PROPERTIES

• Acid pKa: 14.422222
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.7126789
• LogD (pH = 7.4): 2.3968606
• Log P: 3.7834027
• Molar Refractivity: 101.5121 cm^3
• Polarizability: 39.833355 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true