7-hydroxy-5-methoxy-4-methyl-6-{2-[(2S)-2-methyl-5-oxooxolan-2-yl]ethyl}-1,3-dihydro-2-benzofuran-1-one

• ChemBase ID: 174879
• Molecular Formular: C17H20O6
• Molecular Mass: 320.3371
• Monoisotopic Mass: 320.12598836
• SMILES: C1C[C@@](OC1=O)(CCc1c(c(c2c(c1O)C(=O)OC2)C)OC)C
• Canonical SMILES: COc1c(CC[C@@]2(C)CCC(=O)O2)c(O)c2c(c1C)COC2=O
• InChI: InChI=1S/C17H20O6/c1-9-11-8-22-16(20)13(11)14(19)10(15(9)21-3)4-6-17(2)7-5-12(18)23-17/h19H,4-8H2,1-3H3/t17-/m0/s1
• InChIKey: GNWIDHOJWGSPTK-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-5-methoxy-4-methyl-6-{2-[(2S)-2-methyl-5-oxooxolan-2-yl]ethyl}-1,3-dihydro-2-benzofuran-1-one
• IUPAC Traditional name: 7-hydroxy-5-methoxy-4-methyl-6-{2-[(2S)-2-methyl-5-oxooxolan-2-yl]ethyl}-3H-2-benzofuran-1-one
• Synonyms: (S)- 7-Hydroxy-5-methoxy-4-methyl-6-[2-(tetrahydro-2-methyl-5-oxo-2-furanyl)ethyl]-1(3H)-isobenzofuranone; Mycophenolic Acid Lactone (EP Impurity H)

Database IDs

• CAS Number: 79081-87-1
• PubChem SID: 164230789
• PubChem CID: 46782410

CALCULATED PROPERTIES

• Acid pKa: 9.791668
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.2044652
• LogD (pH = 7.4): 3.2027423
• Log P: 3.204487
• Molar Refractivity: 82.6503 cm^3
• Polarizability: 31.90238 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M831535

A degradation product of Mycophenolic Acid. EP Impurity H.

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)