(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate

• ChemBase ID: 174872
• Molecular Formular: C23H30O11
• Molecular Mass: 482.4777
• Monoisotopic Mass: 482.17881178
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)\C)OC)C
• Canonical SMILES: OC[C@@H]1O[C@@H](OC(=O)CC/C(=C/Cc2c(OC)c(C)c3c(c2O)C(=O)OC3)/C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H30O11/c1-10(5-7-15(25)34-23-20(29)19(28)18(27)14(8-24)33-23)4-6-12-17(26)16-13(9-32-22(16)30)11(2)21(12)31-3/h4,14,18-20,23-24,26-29H,5-9H2,1-3H3/b10-4+/t14-,18-,19+,20-,23+/m1/s1
• InChIKey: VCDAVVIRONUCLX-OTFYJODQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
• IUPAC Traditional name: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
• Synonyms: 1-[(4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate] β-D-Glucopyranose; Mycophenolic Acid Acyl-β-D-glucoside

Database IDs

• CAS Number: 344562-78-3
• PubChem SID: 164230782
• PubChem CID: 71750870

CALCULATED PROPERTIES

• Acid pKa: 9.75719
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 1.2595055
• LogD (pH = 7.4): 1.2576407
• Log P: 1.2595294
• Molar Refractivity: 117.6646 cm^3
• Polarizability: 46.042347 Å^3
• Polar Surface Area: 172.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Foam

Safety Information

• Storage Condition: -86?C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M831510

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)