4-(2-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}ethyl)morpholin-4-ium-4-olate

• ChemBase ID: 174870
• Molecular Formular: C23H31NO8
• Molecular Mass: 449.49414
• Monoisotopic Mass: 449.20496696
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)OCC[N+]1(CCOCC1)[O-])\C)OC)C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)OCC[N+]2([O-])CCOCC2)\C)c(O)c2c(c1C)COC2=O
• InChI: InChI=1S/C23H31NO8/c1-15(5-7-19(25)31-13-10-24(28)8-11-30-12-9-24)4-6-17-21(26)20-18(14-32-23(20)27)16(2)22(17)29-3/h4,26H,5-14H2,1-3H3/b15-4+
• InChIKey: MNDAMCFHWPXNAW-SYZQJQIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}ethyl)morpholin-4-ium-4-olate
• IUPAC Traditional name: 4-(2-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}ethyl)morpholin-4-ium-4-olate
• Synonyms: (4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-Oxido-4-morpholinyl)ethyl Ester; EP ImpurityG; Mycophenolate Mofetil N-Oxide (EP Impurity G)

Database IDs

• CAS Number: 224052-51-1
• PubChem SID: 164230780
• PubChem CID: 29984917

CALCULATED PROPERTIES

• Acid pKa: 9.758773
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.3492358
• LogD (pH = 7.4): 2.3473787
• Log P: 2.3492603
• Molar Refractivity: 119.141 cm^3
• Polarizability: 45.09026 Å^3
• Polar Surface Area: 118.17 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M831470

Degradation product of Mycophenolate Mofetyl. EP impurity G.

REFERENCES

• Jones, D., et al.: J. Med. Chem., 14, 305 (1971)
• Ohsugi, Y., et al.: Cancer Res., 36, 2923 (1971)
• Hupe, D., et al.: J. Bio. Chem., 262, 8363 (1971)
• Lee, W., et al.: Int. J. Pharm., 7, 161 (1971)