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

• ChemBase ID: 166520
• Molecular Formular: C22H29NO7
• Molecular Mass: 419.46816
• Monoisotopic Mass: 419.19440227
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)OCCN1CCOCC1)\C)O)C
• Canonical SMILES: O=C(CC/C(=C/Cc1c(O)c(C)c2c(c1O)C(=O)OC2)/C)OCCN1CCOCC1
• InChI: InChI=1S/C22H29NO7/c1-14(4-6-18(24)29-12-9-23-7-10-28-11-8-23)3-5-16-20(25)15(2)17-13-30-22(27)19(17)21(16)26/h3,25-26H,4-13H2,1-2H3/b14-3+
• InChIKey: QGQXAMBOYWULFX-LZWSPWQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(morpholin-4-yl)ethyl (4E)-6-(4,6-dihydroxy-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-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
• Synonyms: Mycophenolate Mofetyl Impurity A; O-Desmethyl Mycophenolate Mofetil(Impurity A)

Database IDs

• CAS Number: 1322681-36-6
• PubChem SID: 162260653
• PubChem CID: 29977541

CALCULATED PROPERTIES

• Acid pKa: 8.60457
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.5535376
• LogD (pH = 7.4): 3.2753377
• Log P: 3.3277416
• Molar Refractivity: 112.6138 cm^3
• Polarizability: 42.99944 Å^3
• Polar Surface Area: 105.53 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Brownish Yellow Gel Low-Melting Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D292076

Mycophenolate mofetyl impurity A.

REFERENCES

• Mackall, J.C., et al.: J. Biol. Chem., 2511, 6462 (1976)
• Nishio, E., et al.: Eur. J. Pharmacol., 301, 203 (1976)
• Zhang, B., et al.: J. Clin. Endocrinol. Metab., 84, 4274 (1976)
• Reusch, J.E.B., et al.: Mol. Cell. Biol., 20, 1008 (1976)