2-[3-(4-bromobenzoyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}phenyl]acetic acid

• ChemBase ID: 162719
• Molecular Formular: C21H22BrNO8
• Molecular Mass: 496.30528
• Monoisotopic Mass: 495.05287867
• SMILES: c1c(c(c(cc1)CC(=O)O)N[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)C(=O)c1ccc(cc1)Br
• Canonical SMILES: OC[C@@H]1O[C@@H](Nc2c(cccc2C(=O)c2ccc(cc2)Br)CC(=O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H22BrNO8/c22-12-6-4-10(5-7-12)17(27)13-3-1-2-11(8-15(25)26)16(13)23-21-20(30)19(29)18(28)14(9-24)31-21/h1-7,14,18-21,23-24,28-30H,8-9H2,(H,25,26)/t14-,18-,19+,20-,21-/m1/s1
• InChIKey: MYPFOYDRLGWLCK-LNCSSOGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(4-bromobenzoyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}phenyl]acetic acid
• IUPAC Traditional name: [3-(4-bromobenzoyl)-2-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}phenyl]acetic acid
• Synonyms: 3-(4-Bromobenzoyl)-2-(β-D-glucopyranosylamino)benzeneacetic Acid; Bromfenac N-β-D-Glucoside

Database IDs

• CAS Number: 212266-82-5
• PubChem SID: 162256854
• PubChem CID: 71314207

CALCULATED PROPERTIES

• Acid pKa: 3.6829755
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.26734084
• LogD (pH = 7.4): -1.7646234
• Log P: 1.5479157
• Molar Refractivity: 113.4198 cm^3
• Polarizability: 43.83115 Å^3
• Polar Surface Area: 156.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B678560

Bromfenac N-β-D-Glucoside is a metabolite of Bromfenac (B678550).

REFERENCES

• Kirkman, S.K., et al.: Drug Metab. Dispos., 26, 720 (1998)