(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169606
• Molecular Formular: C21H18O11
• Molecular Mass: 446.36102
• Monoisotopic Mass: 446.0849114
• SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)c2coc3c(c2=O)c(O)cc(c3)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O11/c22-9-5-12(23)14-13(6-9)30-7-11(15(14)24)8-1-3-10(4-2-8)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21-23,25-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: NHEBJNCJBWUPCK-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxochromen-3-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Genistein-4'-glucuronide; 4-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-3-yl)phenyl β-D-Glucopyranosiduronic Acid; Genistein 4'-β-D-Glucuronide

Database IDs

• CAS Number: 245084-07-5
• PubChem SID: 162263738
• PubChem CID: 45782816

CALCULATED PROPERTIES

• Acid pKa: 3.1858854
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.1936554
• LogD (pH = 7.4): -3.161339
• Log P: 1.1290789
• Molar Refractivity: 103.6947 cm^3
• Polarizability: 40.819016 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Yellow Solid
• Melting Point: 152-154°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - G349990

Genistein (G350000) metabolite.

REFERENCES

• Hosoda, K., et al.: Drug Metab. Disposition, 36, 1485 (2008)
• Bursztyka, J., et al.: Food Chem., Toxicol., 46, 939 (2008)
• Hosoda, K., et al.: Anal. Bioanal. Chem., 397, 1563 (2008)