(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 169358
• Molecular Formular: C22H20O10
• Molecular Mass: 444.3882
• Monoisotopic Mass: 444.10564684
• SMILES: c1(ccc2c(c1)occ(c2=O)c1ccc(cc1)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H20O10/c1-29-11-4-2-10(3-5-11)14-9-30-15-8-12(6-7-13(15)16(14)23)31-22-19(26)17(24)18(25)20(32-22)21(27)28/h2-9,17-20,22,24-26H,1H3,(H,27,28)/t17-,18-,19+,20-,22+/m0/s1
• InChIKey: UMBVLOHYPOQARY-SXFAUFNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 3-(4-Methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; 3-(p-Methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; Formononetin Glucuronide; Formononetin-7-O-Glucuronide; Formononetin 7-O-β-D-Glucuronide

Database IDs

• CAS Number: 18524-03-3
• PubChem SID: 162263490
• PubChem CID: 71316927

CALCULATED PROPERTIES

• Acid pKa: 2.878408
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -1.6434674
• LogD (pH = 7.4): -2.5588346
• Log P: 0.9285382
• Molar Refractivity: 106.1961 cm^3
• Polarizability: 42.03373 Å^3
• Polar Surface Area: 151.98 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F693210

Formononetin 7-O-β-D-Glucuronide is the glucuronide metabolite of Formononetin (F693200).

REFERENCES

• Breinholt, V., et al.: Food Chem. Toxicol., 38, 555 (2000)
• Chen, J., et al.: Drug Metab. Dispos., 33, 1777 (2000)
• Barve, A., et al.: Biopharm. Drug Dispos., 30, 356 (2000)