(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol

• ChemBase ID: 126448
• Molecular Formular: C8H15NO4
• Molecular Mass: 189.209
• Monoisotopic Mass: 189.10010797
• SMILES: O[C@H]1CCN2[C@H]1[C@@H](O)[C@H](O)[C@@H](O)C2
• Canonical SMILES: O[C@@H]1[C@@H](O)CN2[C@@H]([C@H]1O)[C@@H](O)CC2
• InChI: InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
• InChIKey: JDVVGAQPNNXQDW-TVNFTVLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol
• IUPAC Traditional name: castanospermine
• Synonyms: (+)-Castanospermine; (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyoctahydroindolizidine; (1S,6S,7R,8R,8aR)-Octahydro-1,6,7,8-indolizinetetrol; Castanospermine; Castanospermine; 1,6,7,8-Tetrahydroxyoctahydroindolizine; Castanospermine; (1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine; 栗树精胺; (1S,6S,7R,8R,8aR)-1,6,7,8-四羟基八氢吲哚里西定; (1S,6S,7R,8R,8aR)-八氢-1,6,7,8-吲嗪四醇; 1,6,7,8-四羟基八氢吲嗪; 栗树精胺; 栗精胺

Database IDs

• CAS Number: 79831-76-8
• MDL Number: MFCD00017555
• Beilstein Number: 3588654
• PubChem SID: 24892642; 24877905; 162220782
• PubChem CID: 54445
• CHEBI ID: 27860
• CHEMBL: 311226
• Chemspider ID: 49177
• Wikipedia Title: Castanospermine

CALCULATED PROPERTIES

• Acid pKa: 12.890403
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -5.7346234
• LogD (pH = 7.4): -4.122846
• Log P: -2.5544934
• Molar Refractivity: 44.4357 cm^3
• Polarizability: 18.122393 Å^3
• Polar Surface Area: 84.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble20 mg/mL, clear, very faintly yellow; Soluble in water; Water
• Apperance: White Crystalline Solid; White to off-white solid
• Melting Point: 211-214°C; 212-215 °C; 213-217 °C(lit.)
• Optical Rotation: [α]20/D +80°, c = 0.9 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22; R20/21/22
• Safety Statements: 26-36; S26 S36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥94% (GC); ≥95.0% (GC); 98%
• Biological Source: from Castanospermum australe seeds
• Empirical Formula (Hill Notation): C8H15NO4

DETAILS

Sigma Aldrich - C3784

Biochem/physiol Actions
α-glucosidase Inhibitor

Sigma Aldrich - 532673

Packaging
100 mg in glass bottle

Sigma Aldrich - 22100

Biochem/physiol Actions
α-glucosidase Inhibitor
Other Notes
Glycoprotein processing inhibitor1; Inhibits the function of the LDL receptor2; Inhibits human immunodeficiency virus syncytium formation3

Toronto Research Chemicals - C185000

Castanospermine is a plant alkaloid shown to be a potent inhibitor of lysosomal a-or beta- glucosidase. It also inhibits mammalian glucosidase 1 and beta-mannosidase from sweet almonds and fungal beta-xylosidase.

REFERENCES

• Trends Bio. Sci., 9, 32, (1983)
• J. Biol. Chem., 260, 15873-15879 (1983)
• FEBS, 1985, 28 (1986)
• Arch. Biochem. Biophys., 221, 593 (1983)
• Clin. Biochem., 17, 3 (1983)