(2S,3S,4S,5R,6R)-6-[(1S,2S)-2-(tert-butylamino)-1-(3-chlorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167383
• Molecular Formular: C19H28ClNO7
• Molecular Mass: 417.88112
• Monoisotopic Mass: 417.15542992
• SMILES: c1c(cccc1[C@@H]([C@@H](NC(C)(C)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Cl
• Canonical SMILES: C[C@@H]([C@H](c1cccc(c1)Cl)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)NC(C)(C)C
• InChI: InChI=1S/C19H28ClNO7/c1-9(21-19(2,3)4)15(10-6-5-7-11(20)8-10)27-18-14(24)12(22)13(23)16(28-18)17(25)26/h5-9,12-16,18,21-24H,1-4H3,(H,25,26)/t9-,12-,13-,14+,15+,16-,18+/m0/s1
• InChIKey: UHJXGGJVXVCTLU-KEZLRRPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1S,2S)-2-(tert-butylamino)-1-(3-chlorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1S,2S)-2-(tert-butylamino)-1-(3-chlorophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (αR)-rel-3-Chloro-α-[(1R)-1-[(1,1-dimethylethyl)amino]ethyl]benzenemethanol β-D-Glucuronide; rac threo-Hydroxybupropion β-D-Glucuronide; rac threo-Dihydro Bupropion β-D-Glucuronide

Database IDs

• PubChem SID: 162261516
• PubChem CID: 71316066

CALCULATED PROPERTIES

• Acid pKa: 3.1824024
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.94792527
• LogD (pH = 7.4): -0.94855815
• Log P: -0.9468076
• Molar Refractivity: 100.5784 cm^3
• Polarizability: 40.82271 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448680

A glucuronide metabolite of the drug Bupropion (B689625).