[(1R,2S,6S,9R,11R)-11-(hydroxymethyl)-4,4,11-trimethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate

• ChemBase ID: 171384
• Molecular Formular: C12H21NO9S
• Molecular Mass: 355.36144
• Monoisotopic Mass: 355.09370226
• SMILES: O1C[C@@H]2[C@H]([C@H]3[C@@]1(OC(O3)(C)C)COS(=O)(=O)N)O[C@@](O2)(CO)C
• Canonical SMILES: OC[C@]1(C)O[C@H]2[C@@H](O1)[C@@H]1OC(O[C@@]1(OC2)COS(=O)(=O)N)(C)C
• InChI: InChI=1S/C12H21NO9S/c1-10(2)21-9-8-7(19-11(3,5-14)20-8)4-17-12(9,22-10)6-18-23(13,15)16/h7-9,14H,4-6H2,1-3H3,(H2,13,15,16)/t7-,8-,9+,11-,12+/m1/s1
• InChIKey: RWNDWLAEFHRSEG-VZSYODPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,2S,6S,9R,11R)-11-(hydroxymethyl)-4,4,11-trimethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^2,^6]dodecan-6-yl]methyl sulfamate
• IUPAC Traditional name: [(1R,2S,6S,9R,11R)-11-(hydroxymethyl)-4,4,11-trimethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^2,^6]dodecan-6-yl]methyl sulfamate
• Synonyms: 4,5-O-[(1S)-2-Hydroxy-1-methylethylidene]-2,3-O-(1-methylethylidene)-β-D-fructopyranose 1-Sulfamate; 9-Hydroxy Topiramate; S-Hydroxy Topiramate

Database IDs

• CAS Number: 198215-62-2
• PubChem SID: 164227294
• PubChem CID: 29982168

CALCULATED PROPERTIES

• Acid pKa: 11.085729
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -0.57689905
• LogD (pH = 7.4): -0.5769774
• Log P: -0.57689804
• Molar Refractivity: 73.6801 cm^3
• Polarizability: 31.151781 Å^3
• Polar Surface Area: 135.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H969950

A metabolite of Topiramate.

REFERENCES

• Maryanoff, B., et al.: J. Med. Chem., 30, 880 (1987)
• Shank, R., et al.: Epilepsia, 35, 450 (1987)
• Streeter, A., et al.: Drug Metab. Disp., 23, 90 (1987)