(4E)-6-[4-hydroxy-6-(2H3)methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoic acid

• ChemBase ID: 174871
• Molecular Formular: C17H20O6
• Molecular Mass: 320.3371
• Monoisotopic Mass: 320.12598836
• SMILES: c1(c(c(c2c(c1O)C(=O)OC2)C)OC)C/C=C(/CCC(=O)O)\C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O)\C)c(O)c2c(c1C)COC2=O
• InChI: InChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
• InChIKey: HPNSFSBZBAHARI-RUDMXATFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E)-6-[4-hydroxy-6-(^2H₃)methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
• IUPAC Traditional name: (4E)-6-[4-hydroxy-6-(^2H₃)methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
• Synonyms: (4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-d3-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid; Mycophenolic Acid-d3

Database IDs

• PubChem SID: 164230781
• PubChem CID: 45039976

CALCULATED PROPERTIES

• Acid pKa: 3.574788
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6079037
• LogD (pH = 7.4): 0.17404361
• Log P: 3.5275974
• Molar Refractivity: 85.2334 cm^3
• Polarizability: 32.12502 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 132-134°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M831502

Labelled Mycophenolic Acid, an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synth

REFERENCES

• Senda, M., et al.: Transplantation, 60, 1143 (1995)
• Nimmesgern, E., et al.: J. Biol. Chem., 271, 19421 (1995)
• Gummert, J.F., et al.: J. Pharmacol. Exp. Ther., 291, 1100 (1995)