[(3aR,6R,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl sulfamate

• ChemBase ID: 166314
• Molecular Formular: C9H17NO8S
• Molecular Mass: 299.29818
• Monoisotopic Mass: 299.06748751
• SMILES: O1C[C@@H]2[C@H]([C@@H]([C@@]1(O)COS(=O)(=O)N)O)OC(O2)(C)C
• Canonical SMILES: O[C@H]1[C@@H]2OC(O[C@@H]2CO[C@]1(O)COS(=O)(=O)N)(C)C
• InChI: InChI=1S/C9H17NO8S/c1-8(2)17-5-3-15-9(12,4-16-19(10,13)14)7(11)6(5)18-8/h5-7,11-12H,3-4H2,1-2H3,(H2,10,13,14)/t5-,6-,7+,9-/m1/s1
• InChIKey: VQFMBYSMXMIARD-JAGXHNFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aR,6R,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl sulfamate
• IUPAC Traditional name: [(3aR,6R,7S,7aS)-6,7-dihydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]methyl sulfamate
• Synonyms: 4,5-O-(1-Methylethylidene)-β-D-fructopyranose 1-Sulfamate; 2,3-Desisopropylidene Topiramate

Database IDs

• CAS Number: 851957-35-2
• PubChem SID: 162260447
• PubChem CID: 29977351

CALCULATED PROPERTIES

• Acid pKa: 10.158731
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.5754743
• LogD (pH = 7.4): -1.5762104
• Log P: -1.5754648
• Molar Refractivity: 60.095 cm^3
• Polarizability: 25.594572 Å^3
• Polar Surface Area: 137.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 66-68°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D290170

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)