methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-(3-hydroxy-5-iodophenoxy)oxane-2-carboxylate

• ChemBase ID: 171697
• Molecular Formular: C19H21IO11
• Molecular Mass: 552.26791
• Monoisotopic Mass: 552.01285949
• SMILES: O1[C@@H]([C@@H]([C@@H]([C@H]([C@H]1C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)Oc1cc(cc(c1)O)I
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Oc2cc(O)cc(c2)I)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C19H21IO11/c1-8(21)27-14-15(28-9(2)22)17(29-10(3)23)19(31-16(14)18(25)26-4)30-13-6-11(20)5-12(24)7-13/h5-7,14-17,19,24H,1-4H3/t14-,15-,16-,17+,19+/m1/s1
• InChIKey: OASKASZRFUXVAA-RXYDEIHYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-(3-hydroxy-5-iodophenoxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-(3-hydroxy-5-iodophenoxy)oxane-2-carboxylate
• Synonyms: 3-Hydroxy-5-iodophenyl-β-D-glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate; 3-Hydroxy-5-iodophenyl-2’,3’,4’-tri-O-acetyl-β-D-glucuronide Methyl Ester; 5-Iodoresorcinol-2',3',4'-tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 490028-20-1
• PubChem SID: 164227607
• PubChem CID: 71749517

CALCULATED PROPERTIES

• Acid pKa: 8.798921
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.8163197
• LogD (pH = 7.4): 1.7996533
• Log P: 1.8165364
• Molar Refractivity: 107.6177 cm^3
• Polarizability: 44.270313 Å^3
• Polar Surface Area: 143.89 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - I719510

Intermediate for the synthesis of glucuronide conjugates of trans-Resveratrol

REFERENCES

• Learmonth, D.A., et al.: Bioconjug. Chem., 14, 262 (2003)