(4E)-6-(6-methoxy-7-methyl-3-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

• ChemBase ID: 174878
• Molecular Formular: C23H30O11
• Molecular Mass: 482.4777
• Monoisotopic Mass: 482.17881178
• SMILES: c1(c(c(c(c2c1COC2=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)C/C=C(/CCC(=O)O)\C)OC)C
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2c(C/C=C(/CCC(=O)O)\C)c(OC)c(c3c2C(=O)OC3)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H30O11/c1-10(5-7-15(25)26)4-6-12-20(31-3)11(2)13-9-32-22(30)16(13)21(12)34-23-19(29)18(28)17(27)14(8-24)33-23/h4,14,17-19,23-24,27-29H,5-9H2,1-3H3,(H,25,26)/b10-4+/t14-,17-,18+,19-,23+/m1/s1
• InChIKey: PXWZKGRCFSHAMN-OVUIAQIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E)-6-(6-methoxy-7-methyl-3-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• IUPAC Traditional name: (4E)-6-(6-methoxy-7-methyl-3-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
• Synonyms: (4E)-6-[4-(β-D-Glucopyranosyloxy)-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid; Mycophenolic Acid Phenolic β-D-Glucoside

Database IDs

• CAS Number: 55533-52-3
• PubChem SID: 164230788
• PubChem CID: 71750874

CALCULATED PROPERTIES

• Acid pKa: 3.4869657
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.394673
• LogD (pH = 7.4): -2.7697148
• Log P: 0.6095294
• Molar Refractivity: 117.3778 cm^3
• Polarizability: 45.87048 Å^3
• Polar Surface Area: 172.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 85-90°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M831530

A metabolite of Mycophenolic acid (phase II metabolism).

REFERENCES

• Bullingham, R., et al.: J. Clin. Pharmacol., 36, 315 (1996)
• McGurk, K., et al.: Biochem. Pharmacol., 55, 1005 (1996)
• Bowalgaha, K., et al.: Br. J. Clin. Pharmacol., 52, 605 (1996)
• Bernard, O., et al.: Drug Metab. Dispos., 32, 775 (1996)