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

• ChemBase ID: 174883
• Molecular Formular: C22H28O8
• Molecular Mass: 420.45292
• Monoisotopic Mass: 420.17841786
• SMILES: c1(c(c(c2c(c1OCCCCC(=O)O)C(=O)OC2)C)OC)C/C=C(/CCC(=O)O)\C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O)\C)c(OCCCCC(=O)O)c2c(c1C)COC2=O
• InChI: InChI=1S/C22H28O8/c1-13(8-10-18(25)26)7-9-15-20(28-3)14(2)16-12-30-22(27)19(16)21(15)29-11-5-4-6-17(23)24/h7H,4-6,8-12H2,1-3H3,(H,23,24)(H,25,26)/b13-7+
• InChIKey: PFECETFRFNZFKJ-NTUHNPAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4E)-6-[4-(4-carboxybutoxy)-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
• IUPAC Traditional name: (4E)-6-[4-(4-carboxybutoxy)-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl]-4-methylhex-4-enoic acid
• Synonyms: (4E)-6-[4-(4-Carboxybutoxy)-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoic Acid; MPAC; Mycophenolic Acid Carboxybutoxy Ether

Database IDs

• CAS Number: 931407-27-1
• PubChem SID: 164230793
• PubChem CID: 71750878

CALCULATED PROPERTIES

• Acid pKa: 3.1174793
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.65524715
• LogD (pH = 7.4): -3.318664
• Log P: 3.4717174
• Molar Refractivity: 109.8557 cm^3
• Polarizability: 41.95438 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M831555

A metabolite of Mycophenolic Acid (M831500).

REFERENCES

• Wieland, E., et al.: Clin. Biochem., 33, 107 (2000)
• Shipkova, M., et al.: Ther. Drug Monit., 25, 1 (2000)