(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol

• ChemBase ID: 129676
• Molecular Formular: C8H15NO3
• Molecular Mass: 173.2096
• Monoisotopic Mass: 173.10519335
• SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)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)-octahydroindolizine-1,2,8-triol
• IUPAC Traditional name: swainsonine
• Synonyms: Tridolgosir; Swainsonine; 8α,β-Octahydroindolizidine-1α,2α,8β-triol; (-)-Swainsonine

Database IDs

• CAS Number: 72741-87-8
• PubChem SID: 162223965
• PubChem CID: 51683
• CHEMBL: 371197
• Chemspider ID: 46788
• DrugBank ID: DB02034
• KEGG ID: C10173
• Unique Ingredient Identifier: RSY4RK37KQ
• Wikipedia Title: Swainsonine

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: 10 mg/1 mL in water; DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >125°C (dec.); 143-144 °C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S885000

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

• J. Biol. Chem., 258, 7578-7585 (1983)
• Methods Enzymol., 98, 135 (1983)
• EMBO Journal, 3, 551-556 (1983)
• Mol. Cell. Biol., 5, 3467-3475 (1983)
• Int. J. Cancer, 44, 685 (1983)
• Melanoma Res., 1, 43 (1983)
• Bonay, P., & Fresno, M.: Glycobiology, 9(1983)
• 423-4