(1S,3R,5R,6R,8R,9s,10S,12S,13S)-5,6,12,13-tetramethoxy-5,6,12,13-tetramethyl-9-(trifluoromethanesulfonyloxy)-4,7,11,14-tetraoxatricyclo[8.4.0.03,8]tetradecan-2-yl benzoate

• ChemBase ID: 161986
• Molecular Formular: C26H35F3O13S
• Molecular Mass: 644.6085096
• Monoisotopic Mass: 644.17504684
• SMILES: [C@@H]1([C@@H]2OC([C@@](O[C@@H]2C([C@H]2OC([C@](O[C@@H]12)(C)OC)(C)OC)OC(=O)c1ccccc1)(C)OC)(C)OC)OS(=O)(=O)C(F)(F)F
• Canonical SMILES: COC1(C)O[C@@H]2C(OC(=O)c3ccccc3)[C@H]3O[C@](C)(OC)C(O[C@H]3[C@@H]([C@@H]2O[C@@]1(C)OC)OS(=O)(=O)C(F)(F)F)(C)OC
• InChI: InChI=1S/C26H35F3O13S/c1-22(33-5)24(3,35-7)40-18-16(38-22)15(37-21(30)14-12-10-9-11-13-14)17-19(20(18)42-43(31,32)26(27,28)29)41-25(4,36-8)23(2,34-6)39-17/h9-13,15-20H,1-8H3/t15?,16-,17+,18+,19-,20+,22+,23-,24+,25-
• InChIKey: JKOKAMIFWNDNGM-VAWSJCSXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,5R,6R,8R,9s,10S,12S,13S)-5,6,12,13-tetramethoxy-5,6,12,13-tetramethyl-9-(trifluoromethanesulfonyloxy)-4,7,11,14-tetraoxatricyclo[8.4.0.0^3,^8]tetradecan-2-yl benzoate
• IUPAC Traditional name: (1S,3R,5R,6R,8R,9s,10S,12S,13S)-5,6,12,13-tetramethoxy-5,6,12,13-tetramethyl-9-(trifluoromethanesulfonyloxy)-4,7,11,14-tetraoxatricyclo[8.4.0.0^3,^8]tetradecan-2-yl benzoate
• Synonyms: 1,6-O-[(1R,2R)-1,2-Dimethoxy-1,2-dimethyl-1,2-ethanediyl]-3,4-O-[(1S,2S)-1,2-dimethoxy-1,2-dimethyl-1,2-ethanediyl]-myo-inositol 5-Benzoate 2-(1,1,1-Trifluoro-methanesulfonate); 1,6:3,4-Bis-[O-(2,3-dimethoxybutane-2,3-diyl)]-2-O-trifluoromethanesulphonyl-5-O-benzolyl-myo-inositol

Database IDs

• CAS Number: 1068089-34-8
• PubChem SID: 162256121
• PubChem CID: 71313945

CALCULATED PROPERTIES

• H Acceptors: 11
• H Donor: 0
• LogD (pH = 5.5): 5.0951824
• LogD (pH = 7.4): 5.0951824
• Log P: 5.0951824
• Molar Refractivity: 137.0783 cm^3
• Polarizability: 55.94724 Å^3
• Polar Surface Area: 143.51 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: >150°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - B427000

One of the scyllo-Inositol derivatives having effects on amyloid β peptide aggregation. Scyllo-Inositol has shown promise as a potential therapeutic for Alzheimer's disease, by directly interacting with the amyloid β (Aβ) peptide to inhibit Aβ42 fiber for

REFERENCES

• McLaurin, J., et al.: J. Biol. Chem., 275, 18495 (2000)
• Hardy, J., et al.: Science, 297, 353 (2000)
• Cohen, T., et al.: Biochemistry, 45, 4727 (2000)