methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({6-methoxy-5-[(2E)-6-methoxy-3-methyl-6-oxohex-2-en-1-yl]-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)oxane-2-carboxylate

• ChemBase ID: 173994
• Molecular Formular: C25H32O12
• Molecular Mass: 524.51438
• Monoisotopic Mass: 524.18937646
• SMILES: c1(c(c(c(O[C@@H]2O[C@H]([C@H]([C@@H]([C@@H]2O)O)O)C(=O)OC)c2c1COC2=O)C/C=C(/CCC(=O)OC)\C)OC)C
• Canonical SMILES: COC(=O)CC/C(=C/Cc1c(OC)c(C)c2c(c1O[C@@H]1O[C@@H](C(=O)OC)[C@H]([C@@H]([C@@H]1O)O)O)C(=O)OC2)/C
• InChI: InChI=1S/C25H32O12/c1-11(7-9-15(26)32-3)6-8-13-20(33-4)12(2)14-10-35-23(30)16(14)21(13)36-25-19(29)17(27)18(28)22(37-25)24(31)34-5/h6,17-19,22,25,27-29H,7-10H2,1-5H3/b11-6+/t17-,18-,19+,22-,25+/m0/s1
• InChIKey: LMXFNHGLSAWZDI-TUPPYXDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({6-methoxy-5-[(2E)-6-methoxy-3-methyl-6-oxohex-2-en-1-yl]-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({6-methoxy-5-[(2E)-6-methoxy-3-methyl-6-oxohex-2-en-1-yl]-7-methyl-3-oxo-1H-2-benzofuran-4-yl}oxy)oxane-2-carboxylate
• Synonyms: MPAG-bis methyl ester; Methyl 6-[Methyl-β-D-glucuronato]mycophenolate; Methyl Mycophenolic Acid Methyl Ester Glucosiduronate; Mycophenolic Acid Methyl Ester 6-Methyl β-D-Glucuronate

Database IDs

• PubChem SID: 164229904
• PubChem CID: 71750465

CALCULATED PROPERTIES

• Acid pKa: 12.165075
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 1.221592
• LogD (pH = 7.4): 1.2215846
• Log P: 1.221592
• Molar Refractivity: 126.7834 cm^3
• Polarizability: 49.964497 Å^3
• Polar Surface Area: 167.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 56-58°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M831540

A labelled metabolite of 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 t

Toronto Research Chemicals - M323003

Ametabolite of Mycophenoic Acid.

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)