<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3129</id>
  <title>T3D3087</title>
  <common-name>Swainsonine</common-name>
  <description>Swainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). It has been known to cause a potentially lethal central nervous system condition in livestock known as locoism and is a significant cause of economic losses in livestock industries. Along with slaframine, the other biologially active compound of R. leguminicola, it may contribute to a condition called "slobbers syndrome" in livestock that has ingested contaminated feed. (L1248, A3092)</description>
  <cas>72741-87-8</cas>
  <pubchem-id>51683</pubchem-id>
  <chemical-formula>C8H15NO3</chemical-formula>
  <weight>173.105190</weight>
  <appearance>White powder.</appearance>
  <melting-point>143-144°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Swainsonine inhibits the activity of glycoside hydrolases, especially N-linked glycosylation. Inhibition of Golgi mannosidase II and other alpha-mannosidases causes the accumulation of atypical hybrid glycoproteins and oligosaccarides because the proper processing cannot occur. This also results in intracellular vacuolization. (L1248, A3092, A3093)
</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Swainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). (L1248, A3092)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Swainsonine causes a variety of neurological disorders, including locoism and "slobbers syndrome" in livestock. In man it causes a lysosomal storage disease, biochemically and morphologically similar to mannosidosis. It is also an appetite suppressant. (L1248, A3092, A3093)

</health-effects>
  <symptoms>Symptoms of locoism include staggering gait, depression, muscular incoordination, staring, nervousness, hyperexcitability, loss of appetite, and reproductive alterations such as abortion and birth defects. The major symptom of "slobbers syndrome" is profuse salivation. Other symptoms include diarrhea, lacrimation, stiff joints, frequent urination, tremors, spontaneous abortion, labored breathing, loss of appetite, bloat, and possibly death. Swainsonine also causes vacuolation of most tissues. (L1819, A3092, A3093)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-23T18:26:10Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:25:23Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C10173</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Swainsonine</stitch-id>
  <drugbank-id>DB02034</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OC1CN2CCCC(O)C2C1O</moldb-smiles>
  <moldb-formula>C8H15NO3</moldb-formula>
  <moldb-inchi>InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2</moldb-inchi>
  <moldb-inchikey>FXUAIOOAOAVCGD-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">173.2096</moldb-average-mass>
  <moldb-mono-mass type="decimal">173.105193351</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>-1.4</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>5170</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;William H. Pearson, Erik J. Hembre, &amp;#8220;Method for preparing swainsonine.&amp;#8221; U.S. Patent US5919952, issued December, 1986.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002424</chemdb-id>
  <dsstox-id>DTXSID5046356</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00037401</susdat-id>
  <iupac>(1S,2R,8R,8aR)-octahydroindolizine-1,2,8-triol</iupac>
  <moldb-polar-surface-area>63.93000000000001</moldb-polar-surface-area>
  <moldb-refractivity>43.117799999999995</moldb-refractivity>
  <moldb-polarizability>18.1096065809744</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>13.284673320768636</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.470513713136212</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>-1.52</moldb-alogps-logp>
  <moldb-alogps-logs>0.88</moldb-alogps-logs>
  <moldb-alogps-solubility>1.32e+03 g/l</moldb-alogps-solubility>
</compound>
