(2S,3R,4S,5S,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl (4E)-6-{4-[(tert-butyldimethylsilyl)oxy]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl}-4-methylhex-4-enoate

• ChemBase ID: 163356
• Molecular Formular: C35H58O11Si2
• Molecular Mass: 710.99942
• Monoisotopic Mass: 710.35176574
• SMILES: c1(c(c(c(c2c1COC2=O)O[Si](C(C)(C)C)(C)C)C/C=C(/CCC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO[Si](C(C)(C)C)(C)C)\C)OC)C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O[C@@H]2O[C@@H](CO[Si](C(C)(C)C)(C)C)[C@H]([C@@H]([C@@H]2O)O)O)\C)c(O[Si](C(C)(C)C)(C)C)c2c(c1C)COC2=O
• InChI: InChI=1S/C35H58O11Si2/c1-20(15-17-25(36)45-33-29(39)28(38)27(37)24(44-33)19-43-47(10,11)34(3,4)5)14-16-22-30(41-9)21(2)23-18-42-32(40)26(23)31(22)46-48(12,13)35(6,7)8/h14,24,27-29,33,37-39H,15-19H2,1-13H3/b20-14+/t24-,27-,28+,29-,33+/m1/s1
• InChIKey: OSEKHTMTABJUIJ-RPDVICHOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl (4E)-6-{4-[(tert-butyldimethylsilyl)oxy]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl}-4-methylhex-4-enoate
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl (4E)-6-{4-[(tert-butyldimethylsilyl)oxy]-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl}-4-methylhex-4-enoate
• Synonyms: 4,6'-O-(tert-Butyldimethylsilyl)mycophenolic Acid Acyl-β-D-glucoside

Database IDs

• PubChem SID: 162257491
• PubChem CID: 71314412

CALCULATED PROPERTIES

• Acid pKa: 12.197623
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 4.7815
• LogD (pH = 7.4): 4.781493
• Log P: 4.7815
• Molar Refractivity: 177.3608 cm^3
• Polarizability: 74.00957 Å^3
• Polar Surface Area: 150.21 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Dichloromethane; Ethyl Acetate

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B691345

A protected metabolite of Mycophenolic acid (phase II metabolism).

REFERENCES

• Bullingham, R., et al.: J. Clin. Pharmacol., 36, 315 (1996)
• McGurk, K., et al.: Biochem. Pharmacol., 55, 1005 (1996)
• Bowalgaha, K., et al.: Br. J. Clin. Pharmacol., 52, 605 (1996)
• Bernard, O., et al.: Drug Metab. Dispos., 32, 775 (2004)