disodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({5-hydroxy-4-oxo-3-[4-(sulfonatooxy)phenyl]-4H-chromen-7-yl}oxy)oxane-2-carboxylate

• ChemBase ID: 169604
• Molecular Formular: C21H16Na2O14S
• Molecular Mass: 570.38788
• Monoisotopic Mass: 570.00561475
• SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)OS(=O)(=O)[O-])O)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)[O-].[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)occ(c3=O)c2ccc(cc2)OS(=O)(=O)[O-])[C@H]([C@H]([C@@H]1O)O)O.[Na+].[Na+]
• InChI: InChI=1S/C21H18O14S.2Na/c22-12-5-10(33-21-18(26)16(24)17(25)19(34-21)20(27)28)6-13-14(12)15(23)11(7-32-13)8-1-3-9(4-2-8)35-36(29,30)31;;/h1-7,16-19,21-22,24-26H,(H,27,28)(H,29,30,31);;/q;2*+1/p-2/t16-,17-,18+,19-,21+;;/m0../s1
• InChIKey: JZFIWABEFJYNRS-DSGPYVBMSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({5-hydroxy-4-oxo-3-[4-(sulfonatooxy)phenyl]-4H-chromen-7-yl}oxy)oxane-2-carboxylate
• IUPAC Traditional name: disodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({5-hydroxy-4-oxo-3-[4-(sulfonatooxy)phenyl]chromen-7-yl}oxy)oxane-2-carboxylate
• Synonyms: 5-Hydroxy-4-oxo-3-[4-(sulfooxy)phenyl]-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid Disodium Salt; Genistein 7-β-D-Glucuronide 4'-Sulfate Disodium Salt

Database IDs

• PubChem SID: 162263736
• PubChem CID: 71317058

CALCULATED PROPERTIES

• Acid pKa: -2.4968953
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): -4.4168124
• LogD (pH = 7.4): -5.2554426
• Log P: -1.4819682
• Molar Refractivity: 123.4019 cm^3
• Polarizability: 45.51319 Å^3
• Polar Surface Area: 232.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Brownish Red Solid
• Melting Point: >270°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - G349980

Sulfuric Acid conjugated Genistein metabolite.

REFERENCES

• Kinjo, J., et al.: Biol. Pharm. Bull., 27, 185 (2004)
• Tsuchihashi, R., et al.: Nat. Med., 58, 71 (2004)
• Bursztyka, J., et al.: Food Chem. Toxicol., 46, 939 (2004)