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

• ChemBase ID: 169611
• Molecular Formular: C21H18O11
• Molecular Mass: 446.36102
• Monoisotopic Mass: 446.0849114
• SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)O)O)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)occ(c3=O)c2ccc(cc2)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O11/c22-9-3-1-8(2-4-9)11-7-30-13-6-10(5-12(23)14(13)15(11)24)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: JIVINIISUDEORF-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 38482-81-4
• PubChem SID: 162263743
• PubChem CID: 15940724

CALCULATED PROPERTIES

• Acid pKa: 2.738625
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.565248
• LogD (pH = 7.4): -2.415487
• Log P: 1.1290789
• Molar Refractivity: 103.6947 cm^3
• Polarizability: 40.819046 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brown Solid
• Melting Point: >228°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - G350015

Genistein (G350000) metabolite.

REFERENCES

• Zhou, S., et al.: J. Agric. Food Chem., 56, 8354 (2008)
• Hosoda, K., et al.: Drug Metab. Disposition, 36, 1485 (2008)
• Hosoda, K., et al.: Anal. Bioanal., Chem., 397, 1563 (2008)