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

• ChemBase ID: 159777
• Molecular Formular: C21H21NO9
• Molecular Mass: 431.39274
• Monoisotopic Mass: 431.12163126
• 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)c1ccccc1
• Canonical SMILES: O=C(Cc1cccc(c1N)C(=O)c1ccccc1)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H21NO9/c22-14-11(7-4-8-12(14)15(24)10-5-2-1-3-6-10)9-13(23)30-21-18(27)16(25)17(26)19(31-21)20(28)29/h1-8,16-19,21,25-27H,9,22H2,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: YHXPKRBNQLGSSL-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162253912
• PubChem CID: 71313136

CALCULATED PROPERTIES

• Acid pKa: 3.1934633
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.3841962
• LogD (pH = 7.4): -2.5108078
• Log P: 0.7176401
• Molar Refractivity: 104.9401 cm^3
• Polarizability: 41.121407 Å^3
• Polar Surface Area: 176.61 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A576510

Amfenac Acyl-β-D-Glucuronide is a metabolite of Amfenac (A576502).

REFERENCES

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