Structure via PubChem · Public domain (PubChem)
castanospermine
Sign in to saveAlso known as (1S-(1α,6β,7α,8β,8αβ))-octahydro-1,6,7,8-indolizinetetrol, (1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine, 1,6,7,8-tetrahydroxyoctahydroindolizine
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe. It is a potent inhibitor of some glucosidase enzymes and has antiviral activity in vitro and in mouse models.
Chemical data
- Formula
- C8H15NO4
- Molecular weight
- 189.21 g/mol
- IUPAC name
- (1S,6S,7R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,6,7,8-tetrol
- SMILES
- C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O)O)O
- InChIKey
- JDVVGAQPNNXQDW-TVNFTVLESA-N
- XLogP
- -2.2
- Polar surface area
- 84.2 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
565 papers- Castanospermine suppresses CD44 ectodomain cleavage as revealed by transmembrane bioluminescent sensors.Journal of cell science · 2022
- Castanospermine reduces Zika virus infection-associated seizure by inhibiting both the viral load and inflammation in mouse models.Antiviral research · 2020
- The iminosugars celgosivir, castanospermine and UV-4 inhibit SARS-CoV-2 replication.Glycobiology · 2021
- Castanospermine, a tetrahydroxylated alkaloid that inhibits beta-glucosidase and beta-glucocerebrosidase.Archives of biochemistry and biophysics · 1983
- Castanospermine, a potent inhibitor of dengue virus infection in vitro and in vivo.Journal of virology · 2005
via PubMed
Wikidata facts
- Mass
- 189.1
Show 5 more facts
- found in taxon
- Castanospermum australe
- chemical formula
- C₈H₁₅NO₄
- canonical SMILES
- C1CN2CC(C(C(C2C1O)O)O)O
- isomeric SMILES
- C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O)O)O
- Commons category
- Castanospermine
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Biosynthesis
- See also
- References
Castanospermine is an indolizidine alkaloid first isolated from the seeds of Castanospermum australe. It is a potent inhibitor of some glucosidase enzymes and has antiviral activity in vitro and in mouse models.
The castanospermine derivative celgosivir is an antiviral drug candidate that as of 2009 was in development for possible use in treating hepatitis C virus (HCV) infection.
Excerpted from Wikipedia’s “castanospermine” article, available under the CC BY-SA 4.0 licence.