(1R,2R,8aR)-octahydroindolizine-1,2-diol

• ChemBase ID: 172264
• Molecular Formular: C8H15NO2
• Molecular Mass: 157.2102
• Monoisotopic Mass: 157.11027873
• SMILES: C1CCCN2[C@H]1[C@H]([C@@H](C2)O)O
• Canonical SMILES: O[C@@H]1CN2[C@@H]([C@H]1O)CCCC2
• InChI: InChI=1S/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m1/s1
• InChIKey: SQECYPINZNWUTE-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,8aR)-octahydroindolizine-1,2-diol
• IUPAC Traditional name: (1R,2R,8aR)-octahydroindolizine-1,2-diol
• Synonyms: (1R,2R,8aR)-Octahydro-1,2-indolizinediol; [1R-(1α,2β,8aα)]-Octahydro-1,2-indolizinediol; (1R,2R,8aR)-1,2-Dihydroxyindolizidine; (1R,2R,8aR)-Lentiginosine; (-)-Lentiginosine

Database IDs

• CAS Number: 125279-72-3
• PubChem SID: 164228174
• PubChem CID: 130407

CALCULATED PROPERTIES

• Acid pKa: 13.368207
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.7899144
• LogD (pH = 7.4): -2.8638508
• Log P: -0.33189216
• Molar Refractivity: 41.7563 cm^3
• Polarizability: 16.785397 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Beige Solid
• Melting Point: 102-105°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L329000

A selective and powerful inhibitor of amyloglucosidases.

REFERENCES

• Pastuszak, I., et al.: Biochemistry, 29, 1881 (1990)
• Chandra, K., et al.: J. Org. Chem., 67, 4630 (2002)