tridolgosir

Also known as (1S,2R,8R,8AR)-octahydro-1,2,8-indolizinetriol, Swainsonine

Swainsonine is an indolizidine alkaloid. It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug. As a toxin in locoweed (likely its primary toxin) it also is a significant cause of economic losses in livestock industries, particularly in North America. It was first isolated from Swainsona canescens.

Chemical data

Formula: C8H15NO3
Molecular weight: 173.21 g/mol
IUPAC name: (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
InChIKey: FXUAIOOAOAVCGD-WCTZXXKLSA-N
XLogP: -1.3
Polar surface area: 63.9 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 173.105

Show 7 more facts

subject has role: immunologic adjuvant
found in taxon: Fabaceae
chemical formula: C₈H₁₅NO₃
canonical SMILES: C1CC(C2C(C(CN2C1)O)O)O
isomeric SMILES: C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
World Health Organisation international non-proprietary name: tridolgosir
Commons category: Swainsonine

Sources (4)

via Wikidata · CC0

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Encyclopedic overview

9 sections

Contents

Pharmacology
Sources
Biosynthesis
Synthesis
Livestock losses
Potential uses
Molecular mechanism
See also
References

==Pharmacology== Swainsonine inhibits glycoside hydrolases, specifically those involved in N-linked glycosylation. Disruption of Golgi alpha-mannosidase II with swainsonine induces hybrid-type glycans. These glycans have a Man5GlcNAc2 core with processing on the 3-arm that resembles so-called complex-type glycans.

Excerpted from Wikipedia’s “tridolgosir” article, available under the CC BY-SA 4.0 licence.