[4-(4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}-4H-chromen-3-yl)phenyl]oxidanesulfonic acid

• ChemBase ID: 165361
• Molecular Formular: C28H26O16S
• Molecular Mass: 650.56144
• Monoisotopic Mass: 650.09415575
• SMILES: c1(ccc2c(c1)occ(c2=O)c1ccc(cc1)OS(=O)(=O)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)OS(=O)(=O)O)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H26O16S/c1-13(29)39-23-24(40-14(2)30)26(41-15(3)31)28(43-25(23)27(33)37-4)42-18-9-10-19-21(11-18)38-12-20(22(19)32)16-5-7-17(8-6-16)44-45(34,35)36/h5-12,23-26,28H,1-4H3,(H,34,35,36)/t23-,24-,25-,26+,28+/m0/s1
• InChIKey: YLYDFNVTVUNKCE-YYDZWWTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}-4H-chromen-3-yl)phenyl]oxidanesulfonic acid
• IUPAC Traditional name: [4-(4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}chromen-3-yl)phenyl]oxidanesulfonic acid
• Synonyms: 3-(4-Hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate 4’-Sulfate; Daidzein 7-Tri-O-acetyl-β-D-glucuronic Acid Methyl Ester 4'-Sulfate

Database IDs

• CAS Number: 1041261-16-8
• PubChem SID: 162259494
• PubChem CID: 71315166

CALCULATED PROPERTIES

• Acid pKa: -2.423266
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): -0.5997965
• LogD (pH = 7.4): -0.59979767
• Log P: 1.7766011
• Molar Refractivity: 143.9292 cm^3
• Polarizability: 58.66667 Å^3
• Polar Surface Area: 213.56 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Colourless Solid

DETAILS

Toronto Research Chemicals - D103535

Protected Daidzein metabolite.

REFERENCES

• Soidinsalo, O., et al.: Steroids, 72, 851 (2007)