(1S,2R,8R,8aR)-octahydro(6,7-3H2)indolizine-1,2,8-triol

• ChemBase ID: 177971
• Molecular Formular: C8H15NO3
• Molecular Mass: 173.2096
• Monoisotopic Mass: 173.10519335
• SMILES: C1CCN2[C@H]([C@@H]1O)[C@@H]([C@@H](C2)O)O
• Canonical SMILES: O[C@@H]1CN2[C@@H]([C@@H]1O)[C@H](O)CCC2
• InChI: InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
• InChIKey: FXUAIOOAOAVCGD-WCTZXXKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,8aR)-octahydro(6,7-^3H₂)indolizine-1,2,8-triol
• IUPAC Traditional name: (1S,2R,8R,8aR)-octahydro(6,7-^3H₂)indolizine-1,2,8-triol
• Synonyms: 8α,β-Octahydroindolizidine-1α,2α,8β-triol-6-t,7-t; Swainsonine-6,7-3H

Database IDs

• PubChem SID: 164233881
• PubChem CID: 45040453

CALCULATED PROPERTIES

• Acid pKa: 13.284674
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.78174
• LogD (pH = 7.4): -3.4669168
• Log P: -1.4067957
• Molar Refractivity: 43.1178 cm^3
• Polarizability: 17.444298 Å^3
• Polar Surface Area: 63.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (hot); Methanol; Water
• Apperance: Off-White Crystalline Solid

Safety Information

• Storage Warning: Sp. Act. 50 mCi/mmol

DETAILS

Toronto Research Chemicals - S885500

Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of

REFERENCES

• Klein, J.-L. D., et al.: Br. J. Cancer, 80, 87 (1999)