(1S,2R,6R,7R,8S,8aS)-octahydroindolizine-1,2,6,7,8-pentol

• ChemBase ID: 167879
• Molecular Formular: C8H15NO5
• Molecular Mass: 205.2084
• Monoisotopic Mass: 205.09502259
• SMILES: [C@H]1([C@@H](CN2[C@H]([C@@H]1O)[C@@H]([C@@H](C2)O)O)O)O
• Canonical SMILES: O[C@@H]1CN2C[C@H]([C@H]([C@H]2[C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C8H15NO5/c10-3-1-9-2-4(11)7(13)8(14)5(9)6(3)12/h3-8,10-14H,1-2H2/t3-,4-,5+,6-,7-,8+/m1/s1
• InChIKey: KSWHMQGAWBUNLD-RDULZCEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6R,7R,8S,8aS)-octahydroindolizine-1,2,6,7,8-pentol
• IUPAC Traditional name: (1S,2R,6R,7R,8S,8aS)-octahydroindolizine-1,2,6,7,8-pentol
• Synonyms: (1S,2R,6R,7R,8S,8aS)-Octahydro-1,2,6,7,8-indolizinepentol; 6,7-Dihydroxyswainsonine

Database IDs

• CAS Number: 144367-16-8
• PubChem SID: 162262012
• PubChem CID: 10867451

CALCULATED PROPERTIES

• Acid pKa: 12.757111
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -6.0413866
• LogD (pH = 7.4): -4.2770276
• Log P: -3.2447882
• Molar Refractivity: 45.5328 cm^3
• Polarizability: 18.81549 Å^3
• Polar Surface Area: 104.39 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D455000

Swainsonine analogue; inhibits a-mannosidase with 20-to 100-fold less activity.

REFERENCES

• Chen, Y., et al.: Tetrahedron Letters, 33, 34, 4917 (1992)
• Dime, D.S., et al.: Biochemical Pharmacology, 46, 8, 1459 (1993)