Structure via PubChem · Public domain (PubChem)
tridolgosir
Sign in to saveAlso 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.
In the Vinony graph
Vinony's link graph records 186 inbound references to tridolgosir, and connects out to carbohydrate, drug and digital object identifier.
It is catalogued under topics including Alkaloids found in Fabaceae, Chembox image size set and Chemical articles with multiple compound IDs.
Vinony links it to 12 Wikipedia language editions.
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 Ų
- 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
via Wikidata · CC0
~6 min read
Encyclopedic overview
9 sectionsContents
- Pharmacology
- Sources
- Biosynthesis
- Synthesis
- Livestock losses
- Potential uses
- Molecular mechanism
- See also
- References
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.
==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.