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

• ChemBase ID: 1800
• Molecular Formular: C8H15NO3
• Molecular Mass: 173.2096
• Monoisotopic Mass: 173.10519335
• SMILES: O[C@H]1CCCN2C[C@@H](O)[C@@H](O)[C@H]12
• 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+/m0/s1
• InChIKey: FXUAIOOAOAVCGD-FKSUSPILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,8aS)-octahydroindolizine-1,2,8-triol
• IUPAC Traditional name: @swainsonine
• Synonyms: Swainsonine

Database IDs

• CAS Number: 72741-87-8
• PubChem SID: 46506581; 160965256
• PubChem CID: 10975968

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -1.52
• LOG S: 0.88
• Solubility (Water): 1.32e+03 g/l

DETAILS

DrugBank - DB02034

• Drug Groups: experimental
• Description: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity. [PubChem]
• External Links: Wikipedia