2-(morpholin-4-yl)ethyl (4E)-6-[4-(2H3)methoxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate

• ChemBase ID: 173938
• Molecular Formular: C24H33NO7
• Molecular Mass: 447.52132
• Monoisotopic Mass: 447.2257024
• SMILES: c1(c(c(c(c2c1COC2=O)OC)C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)OCCN2CCOCC2)\C)c(OC)c2c(c1C)COC2=O
• InChI: InChI=1S/C24H33NO7/c1-16(6-8-20(26)31-14-11-25-9-12-30-13-10-25)5-7-18-22(28-3)17(2)19-15-32-24(27)21(19)23(18)29-4/h5H,6-15H2,1-4H3/b16-5+
• InChIKey: KOEZVGVALFAIMS-FZSIALSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(morpholin-4-yl)ethyl (4E)-6-[4-(^2H₃)methoxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoate
• IUPAC Traditional name: 2-(morpholin-4-yl)ethyl (4E)-6-[4-(^2H₃)methoxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoate
• Synonyms: Mycophenolate Mofetil EP Impurity D-d3; (4E)-6-(1,3-Dihydro-4,6-dimethoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid 2-(4-Morpholinyl)ethyl Ester-d3; O-Methyl-d3 Mycophenolate Mofetil (d3 Major)(EP Impurity D)

Database IDs

• PubChem SID: 164229848
• PubChem CID: 71750449

CALCULATED PROPERTIES

• Acid pKa: 15.082333
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.19559
• LogD (pH = 7.4): 2.9432771
• Log P: 2.9695296
• Molar Refractivity: 121.5784 cm^3
• Polarizability: 46.8073 Å^3
• Polar Surface Area: 83.53 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M320547

The labelled analogue of O-Methyl Mycophenolate Mofetil, a degradation product of Mycophenolate Mofetil (M831450). EP Impurity D.

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)