methyl (2S,3S,4S,5R,6S)-6-(4-{7-[(2,2-dimethylpropanoyl)oxy]-5-hydroxy-4-oxo-4H-chromen-3-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 176816
• Molecular Formular: C27H28O12
• Molecular Mass: 544.50402
• Monoisotopic Mass: 544.15807634
• SMILES: c1(cc(c2c(c1)occ(c2=O)c1ccc(cc1)O[C@@H]1O[C@H]([C@H]([C@H](O)[C@@H]1O)O)C(=O)OC)O)OC(=O)C(C)(C)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)c2coc3c(c2=O)c(O)cc(c3)OC(=O)C(C)(C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H28O12/c1-27(2,3)26(34)38-14-9-16(28)18-17(10-14)36-11-15(19(18)29)12-5-7-13(8-6-12)37-25-22(32)20(30)21(31)23(39-25)24(33)35-4/h5-11,20-23,25,28,30-32H,1-4H3/t20-,21-,22+,23-,25+/m0/s1
• InChIKey: IKZCYCKFOMGAHK-LYVDORBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-6-(4-{7-[(2,2-dimethylpropanoyl)oxy]-5-hydroxy-4-oxo-4H-chromen-3-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-6-(4-{7-[(2,2-dimethylpropanoyl)oxy]-5-hydroxy-4-oxochromen-3-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 7-O-Pivaloyl-genistein 4'-β-D-Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164232726
• PubChem CID: 71751712

CALCULATED PROPERTIES

• Acid pKa: 8.08887
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 2.9842272
• LogD (pH = 7.4): 2.905189
• Log P: 2.9853356
• Molar Refractivity: 131.3177 cm^3
• Polarizability: 52.190968 Å^3
• Polar Surface Area: 178.28 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Colorless Solid

DETAILS

Toronto Research Chemicals - P550735

Intermediate in the synthesis of Genistein 4’-β-D-Glucuronide (G349990)