methyl (4E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate

• ChemBase ID: 166523
• Molecular Formular: C17H20O6
• Molecular Mass: 320.3371
• Monoisotopic Mass: 320.12598836
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)OC)\C)O)C
• Canonical SMILES: COC(=O)CC/C(=C/Cc1c(O)c(C)c2c(c1O)C(=O)OC2)/C
• InChI: InChI=1S/C17H20O6/c1-9(5-7-13(18)22-3)4-6-11-15(19)10(2)12-8-23-17(21)14(12)16(11)20/h4,19-20H,5-8H2,1-3H3/b9-4+
• InChIKey: ONBUUVPMBJOPQE-RUDMXATFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
• IUPAC Traditional name: methyl (4E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
• Synonyms: (4E)-6-(1,3-Dihydro-4,6-dihydroxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid Methyl Ester; Demethylmycophenolic Acid Methyl Ester; Nor-O-methyl Mycophenolic Acid Methyl Ester; O-Desmethyl Mycophenolic Acid Methyl Ester

Database IDs

• CAS Number: 33431-38-8
• PubChem SID: 162260656
• PubChem CID: 29938276

CALCULATED PROPERTIES

• Acid pKa: 8.602898
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.5272574
• LogD (pH = 7.4): 3.5013704
• Log P: 3.5275974
• Molar Refractivity: 85.5202 cm^3
• Polarizability: 32.298985 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292080

Protected metabolite of Mycophenolic Acid.

REFERENCES

• Nelson, P., et al.: J. Med. Chem., 39, 4181 (1996)
• Ubukata, M., et al.: Bioorg. Med. Chem. Lett., 17, 4767 (1996)