(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol

• ChemBase ID: 126053
• Molecular Formular: C32H31BrN2O2
• Molecular Mass: 555.50474
• Monoisotopic Mass: 554.15689024
• SMILES: Brc1ccc2nc(OC)c(cc2c1)[C@@H](c1ccccc1)[C@](O)(c1c2ccccc2ccc1)CCN(C)C
• Canonical SMILES: COc1nc2ccc(cc2cc1[C@H]([C@](c1cccc2c1cccc2)(CCN(C)C)O)c1ccccc1)Br
• InChI: InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1
• InChIKey: QUIJNHUBAXPXFS-XLJNKUFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
• IUPAC Traditional name: (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
• Brand Name: Sirturo
• Synonyms: TMC207; R207910; AIDS222089; Bedaquiline

Database IDs

• CAS Number: 654653-81-3
• PubChem SID: 162220394
• PubChem CID: 5388906; 5746640
• Chemspider ID: 4534966
• Unique Ingredient Identifier: 78846I289Y
• Wikipedia Title: Bedaquiline

CALCULATED PROPERTIES

• Acid pKa: 13.606679
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.9780622
• LogD (pH = 7.4): 5.610202
• Log P: 7.1326175
• Molar Refractivity: 154.0234 cm^3
• Polarizability: 61.923874 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only (US)
• Pregnancy Category: B (US)
• US Licence: Bedaquiline