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

• ChemBase ID: 165351
• Molecular Formular: C21H18O10
• Molecular Mass: 430.36162
• Monoisotopic Mass: 430.08999678
• SMILES: c1(ccc2c(c1)occ(c2=O)c1ccc(cc1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)c2coc3c(c2=O)ccc(c3)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O10/c22-10-3-6-12-14(7-10)29-8-13(15(12)23)9-1-4-11(5-2-9)30-21-18(26)16(24)17(25)19(31-21)20(27)28/h1-8,16-19,21-22,24-26H,(H,27,28)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: ATUYSKUVHUPXBV-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 264236-77-3
• PubChem SID: 162259484
• PubChem CID: 23930394

CALCULATED PROPERTIES

• Acid pKa: 3.186248
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.5504488
• LogD (pH = 7.4): -3.6115386
• Log P: 0.78264415
• Molar Refractivity: 101.7138 cm^3
• Polarizability: 40.144634 Å^3
• Polar Surface Area: 162.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol
• Apperance: Pale Yellow Solid
• Melting Point: 155-159°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D103490

Daidzein (D103500) metabolite.

REFERENCES

• Fang, N., et al.: J. Agric. Food Chem., 50, 2700 (2002)
• Tsuchihashi, R., et al.: Nat. Med., 58, 71 (2002)
• Hosoda, K., et al.: Drug Metab. Disposition, 36, 1485 (2002)