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Swainsonine information


Swainsonine
Names
Preferred IUPAC name
(1S,2R,8R,8aR)-Octahydroindolizine-1,2,8-triol
Other names
Tridolgosir
Identifiers
CAS Number
  • 72741-87-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9367 ☒N
ChEMBL
  • ChEMBL371197 checkY
ChemSpider
  • 46788 checkY
DrugBank
  • DB02034 checkY
ECHA InfoCard 100.123.531 Edit this at Wikidata
KEGG
  • C10173 checkY
PubChem CID
  • 51683
UNII
  • RSY4RK37KQ checkY
CompTox Dashboard (EPA)
  • DTXSID5046356 Edit this at Wikidata
InChI
  • InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1 checkY
    Key: FXUAIOOAOAVCGD-WCTZXXKLSA-N checkY
  • InChI=1/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
    Key: FXUAIOOAOAVCGD-WCTZXXKLBP
  • InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
    Key: FXUAIOOAOAVCGD-WCTZXXKLSA-N
SMILES
  • C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
Properties
Chemical formula
C8H15NO3
Molar mass 173.2
Melting point 143 to 144 °C (289 to 291 °F; 416 to 417 K)
Solubility in water
10 mg/1 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Swainsonine is an indolizidine alkaloid. It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug.[1] As a toxin in locoweed (likely its primary toxin[2]) it also is a significant cause of economic losses in livestock industries, particularly in North America. It was first isolated from Swainsona canescens.[3]

  1. ^ "NCATS Inxight: Drugs". drugs.ncats.io. Retrieved 2020-01-22.
  2. ^ Stegelmeier BL, Molyneux RJ, Elbein AD, James LF (May 1995). "The lesions of locoweed (Astragalus mollissimus), swainsonine, and castanospermine in rats". Veterinary Pathology. 32 (3): 289–98. doi:10.1177/030098589503200311. PMID 7604496. S2CID 45016726.
  3. ^ Dorling PR, Huxtable CR, Colegate SM (November 1980). "Inhibition of lysosomal alpha-mannosidase by swainsonine, an indolizidine alkaloid isolated from Swainsona canescens". The Biochemical Journal. 191 (2): 649–51. doi:10.1042/bj1910649. PMC 1162258. PMID 6786280.

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Swainsonine

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Swainsonine is an indolizidine alkaloid. It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug...

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Locoweed

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North America for any plant that produces swainsonine, an alkaloid harmful to livestock. Worldwide, swainsonine is produced by a small number of species...

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Chris McCandless

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that McCandless might have been poisoned by a toxic alkaloid called swainsonine, after eating sweet-vetch seeds (Hedysarum alpinum or Hedysarum mackenzii)...

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Ipomoea carnea

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toxic and it can be hazardous to cattle; the toxicity is related to the swainsonine produced by its endophytes, and to bioaccumulation of selenium in the...

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Oxytropis lambertii

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most frequently implicated in livestock poisoning. The toxin is called swainsonine. Research suggests that the plant itself may not be toxic, but becomes...

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Indolizidine alkaloids

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produced as metabolites by fungi and bacteria. For instance, Slaframine and swainsonine were identified in the fungus Rhizoctonia leguminicola, while Castanospermine...

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Indolizine

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are indolizidine, which are found in a variety of alkaloids such as swainsonine. International Union of Pure and Applied Chemistry (2014). Nomenclature...

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Slafractonia leguminicola

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and swainsonine. "Bloat in Camelids". Croom WJ, Hagler WM, Froetschel MA, Johnson AD (May 1995). "The involvement of slaframine and swainsonine in slobbers...

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Oxytropis sericea

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a type of congestive heart failure. The toxic agent in the plant is swainsonine, an alkaloid. Animals affected include cattle, sheep, horses, goats,...

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Fish

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Solasodamine Solasodine Solasonine Solauricidine Solauricine Strychnine Swainsonine Tagetitoxin Tinyatoxin Tomatine Toxalbumin Abrin Ricin Tutin Invertebrate...

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Alkaloid

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δ-semialdehyde of α-aminoadipic acid → pipecolic acid → 1 indolizidinone Swainsonine, castanospermine Pyridine derivatives Simple derivatives of pyridine...

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Indolizidine

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compound that forms the central core of the indolizidine alkaloids such as swainsonine and castanospermine. Indole Indolizine Tryptophan Tryptamine Skvortsov...

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Tetrodotoxin

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Clostridium botulinum

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Ricin

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Glycoside hydrolase

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heterocycles have been found in nature, including deoxynojirimycin, swainsonine, australine and castanospermine. From these natural templates many other...

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Ciguatera fish poisoning

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Solasodamine Solasodine Solasonine Solauricidine Solauricine Strychnine Swainsonine Tagetitoxin Tinyatoxin Tomatine Toxalbumin Abrin Ricin Tutin Invertebrate...

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Amatoxin

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Astragalus mollissimus

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them to "go loco." This is caused by an alkaloid it contains called swainsonine, formerly known as locoine. The plant is toxic both fresh and dried,...

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Lipopolysaccharide

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Tetanus toxin

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Muscimol

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C8H15NO3

Last Update:

mass: 173.21 g/mol, exact mass: 173.1052 u) may refer to: Acetylleucine Swainsonine SCH-50911 This set index page lists chemical structure articles associated...

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Swainsona

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known to produce swainsonine, a phytotoxin harmful to livestock (see Locoweed). In Australia, animals intoxicated with swainsonine are said to be pea...

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Exotoxin

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Cardiotoxicity

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Shiga toxin

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Solasodamine Solasodine Solasonine Solauricidine Solauricine Strychnine Swainsonine Tagetitoxin Tinyatoxin Tomatine Toxalbumin Abrin Ricin Tutin Invertebrate...

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