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

• ChemBase ID: 174876
• Molecular Formular: C23H28O12
• Molecular Mass: 496.46122
• Monoisotopic Mass: 496.15807634
• SMILES: c1(c(c(c(c2c1COC2=O)O)C/C=C(/CCC(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H]([C@@H]1O)O)C(=O)O)\C)OC)C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)\C)c(O)c2c(c1C)COC2=O
• InChI: InChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1
• InChIKey: QBMSTEZXAMABFF-UEARNRKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
• Synonyms: 1-[(4E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-1-oxo-4-hexenoate] β-D-Glucopyranuronic Acid; Mycophenolic Acid Acyl-β-D-glucuronide

Database IDs

• CAS Number: 99043-04-6
• PubChem SID: 164230786
• PubChem CID: 10028772

CALCULATED PROPERTIES

• Acid pKa: 3.2614963
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.6395502
• LogD (pH = 7.4): -1.8560599
• Log P: 1.579804
• Molar Refractivity: 117.532 cm^3
• Polarizability: 46.024822 Å^3
• Polar Surface Area: 189.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Pale Yellow Solid
• Melting Point: 90-93°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M831525

A metabolite of Mycophenolic Acid.

REFERENCES

• Shipkova, M., et al.: Therap. Drug Monit., 24, 390 (2002)
• Picard, N., et al.: Drug Metab. Dispos., 33, 139 (2002)