(2S,3S,4S,5R,6S)-6-({2-[2-amino-3-(4-bromobenzoyl)phenyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 162720
• Molecular Formular: C21H20BrNO9
• Molecular Mass: 510.2888
• Monoisotopic Mass: 509.03214323
• SMILES: c1c(c(c(cc1)CC(=O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)N)C(=O)c1ccc(cc1)Br
• Canonical SMILES: O=C(Cc1cccc(c1N)C(=O)c1ccc(cc1)Br)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H20BrNO9/c22-11-6-4-9(5-7-11)15(25)12-3-1-2-10(14(12)23)8-13(24)31-21-18(28)16(26)17(27)19(32-21)20(29)30/h1-7,16-19,21,26-28H,8,23H2,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: DGEAGYNQPHUIAA-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[2-amino-3-(4-bromobenzoyl)phenyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[2-amino-3-(4-bromobenzoyl)phenyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-Amino-3-(4-bromobenzoyl)benzeneacetyl β-D-Glucopyranosiduronic Acid; Bromfenac Acyl-β-D-Glucuronide

Database IDs

• PubChem SID: 162256855
• PubChem CID: 71314208

CALCULATED PROPERTIES

• Acid pKa: 3.1833305
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.61575985
• LogD (pH = 7.4): -1.7421165
• Log P: 1.5216844
• Molar Refractivity: 112.5629 cm^3
• Polarizability: 44.06751 Å^3
• Polar Surface Area: 176.61 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B678565

Bromfenac Acyl-β-D-Glucuronide is a metabolite of Bromfenac (B678550).

REFERENCES

• Kaspersen, F.M., et al.: Xenobiotica, 17, 1451 (1987)
• Spahn-Langguth, H., et al.: Drug Metab. Rev., 24, 5 (1987)