Swainsonine (T3D3087)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (10)XML
Targets (10)
Record Information
Version2.0
Creation Date2009-07-23 18:26:10 UTC
Update Date2014-12-24 20:25:58 UTC
Accession NumberT3D3087
Identification
Common NameSwainsonine
ClassSmall Molecule
DescriptionSwainsonine 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. (4, 1)
Compound Type
  • Amine
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(-)-(1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine Hydrochloride
(1S, 2R, 8R, 8AR)-1,2,8-Indolizidinetriol
(1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol
(1S,2R,8R,8aR)-Octahydro-indolizine-1,2,8-triol
1S-8AB-Octahydro-indolizidine-1A,2A,8B-triol
Octahydro-1,2,8-indolizinetriol hydrochloride
SWA
Swainsonine Hydrochloride
SWS
Tridolgosir
Chemical FormulaC8H15NO3
Average Molecular Mass173.210 g/mol
Monoisotopic Mass173.105 g/mol
CAS Registry Number72741-87-8
IUPAC Nameoctahydroindolizine-1,2,8-triol
Traditional Nameoctahydroindolizine-1,2,8-triol
SMILESOC1CN2CCCC(O)C2C1O
InChI IdentifierInChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2
InChI KeyInChIKey=FXUAIOOAOAVCGD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndolizidines
Sub ClassNot Available
Direct ParentIndolizidines
Alternative Parents
Substituents
  • Indolizidine
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point143-144°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1320 g/LALOGPS
logP-1.5ALOGPS
logP-1.4ChemAxon
logS0.88ALOGPS
pKa (Strongest Acidic)13.28ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.93 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.12 m³·mol⁻¹ChemAxon
Polarizability18.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3900000000-fa3ee98b35bc181564582021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-af27f13c36318fe110f32016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1900000000-afb1adf231f02c9bee972016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4900000000-f18b9efbfeac2f00516c2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-5fcf910ef2eee1aaeab52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-1900000000-a4f22679f524611c0d782016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-8c00652a95cc25a8acbb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-e9dac584c857b5760ac32021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-0900000000-66417828119342afecdf2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9100000000-0f56b431ab6b0a7547cd2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-f31ec28dc8af4da871102021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-0166941b80b892d623ee2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9500000000-bd83df587f7d40c8015b2021-10-12View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
Mechanism of ToxicitySwainsonine 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. (4, 1, 2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesSwainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). (4, 1)
Minimum Risk LevelNot Available
Health EffectsSwainsonine 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. (4, 1, 2)
SymptomsSymptoms 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. (6, 1, 2)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02034
HMDB IDNot Available
PubChem Compound ID51683
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC10173
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDSwainsonine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis Reference

William H. Pearson, Erik J. Hembre, “Method for preparing swainsonine.” U.S. Patent US5919952, issued December, 1986.

MSDST3D3087.pdf
General References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
  3. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  4. Wikipedia. Swainsonine. Last Updated 7 July 2009. [Link]
  5. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
  6. Wikipedia. Locoweed. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Alpha-mannosidase 2
General Function:
Zinc ion binding
Specific Function:
Catalyzes the first committed step in the biosynthesis of complex N-glycans. It controls conversion of high mannose to complex N-glycans; the final hydrolytic step in the N-glycan maturation pathway.
Gene Name:
MAN2A1
Uniprot ID:
Q16706
Molecular Weight:
131139.485 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
  3. Wikipedia. Swainsonine. Last Updated 7 July 2009. [Link]
Target Details
2. Lysosomal alpha-mannosidase
General Function:
Zinc ion binding
Specific Function:
Necessary for the catabolism of N-linked carbohydrates released during glycoprotein turnover. Cleaves all known types of alpha-mannosidic linkages.
Gene Name:
MAN2B1
Uniprot ID:
O00754
Molecular Weight:
113743.26 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC500.01 uMNot AvailableBindingDB 50168995
IC500.05 uMNot AvailableBindingDB 50168995
IC5020 uMNot AvailableBindingDB 50168995
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
  3. Fiaux H, Kuntz DA, Hoffman D, Janzer RC, Gerber-Lemaire S, Rose DR, Juillerat-Jeanneret L: Functionalized pyrrolidine inhibitors of human type II alpha-mannosidases as anti-cancer agents: optimizing the fit to the active site. Bioorg Med Chem. 2008 Aug 1;16(15):7337-46. doi: 10.1016/j.bmc.2008.06.021. Epub 2008 Jun 14. [18599296 ]
Target Details
3. Alpha-mannosidase 2C1
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
MAN2C1
Uniprot ID:
Q9NTJ4
Molecular Weight:
115834.355 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
4. Alpha-mannosidase 2x
General Function:
Zinc ion binding
Specific Function:
Catalyzes the first committed step in the biosynthesis of complex N-glycans. It controls conversion of high mannose to complex N-glycans; the final hydrolytic step in the N-glycan maturation pathway.
Gene Name:
MAN2A2
Uniprot ID:
P49641
Molecular Weight:
130537.495 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
5. Endoplasmic reticulum mannosyl-oligosaccharide 1,2-alpha-mannosidase
General Function:
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function:
Involved in glycoprotein quality control targeting of misfolded glycoproteins for degradation. It primarily trims a single alpha-1,2-linked mannose residue from Man(9)GlcNAc(2) to produce Man(8)GlcNAc(2), but at high enzyme concentrations, as found in the ER quality control compartment (ERQC), it further trims the carbohydrates to Man(5-6)GlcNAc(2).
Gene Name:
MAN1B1
Uniprot ID:
Q9UKM7
Molecular Weight:
79579.18 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
6. Epididymis-specific alpha-mannosidase
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
MAN2B2
Uniprot ID:
Q9Y2E5
Molecular Weight:
113978.29 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
7. Glycoprotein endo-alpha-1,2-mannosidase
General Function:
Glycoprotein endo-alpha-1,2-mannosidase activity
Specific Function:
Not Available
Gene Name:
MANEA
Uniprot ID:
Q5SRI9
Molecular Weight:
53670.425 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
8. Mannosyl-oligosaccharide 1,2-alpha-mannosidase IA
General Function:
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function:
Involved in the maturation of Asn-linked oligosaccharides. Progressively trim alpha-1,2-linked mannose residues from Man(9)GlcNAc(2) to produce Man(5)GlcNAc(2).
Gene Name:
MAN1A1
Uniprot ID:
P33908
Molecular Weight:
72967.88 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
9. Mannosyl-oligosaccharide 1,2-alpha-mannosidase IB
General Function:
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function:
Involved in the maturation of Asn-linked oligosaccharides. Progressively trim alpha-1,2-linked mannose residues from Man(9)GlcNAc(2) to produce Man(5)GlcNAc(2).
Gene Name:
MAN1A2
Uniprot ID:
O60476
Molecular Weight:
73002.93 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]
Target Details
10. Mannosyl-oligosaccharide 1,2-alpha-mannosidase IC
General Function:
Mannosyl-oligosaccharide 1,2-alpha-mannosidase activity
Specific Function:
Involved in the maturation of Asn-linked oligosaccharides. Trim alpha-1,2-linked mannose residues from Man(9)GlcNAc(2) to produce first Man(8)GlcNAc(2) then Man(6)GlcNAc and a small amount of Man(5)GlcNAc.
Gene Name:
MAN1C1
Uniprot ID:
Q9NR34
Molecular Weight:
70910.025 Da
References
  1. Croom WJ Jr, Hagler WM Jr, Froetschel MA, Johnson AD: The involvement of slaframine and swainsonine in slobbers syndrome: a review. J Anim Sci. 1995 May;73(5):1499-508. [7665382 ]
  2. Broquist HP: The indolizidine alkaloids, slaframine and swainsonine: contaminants in animal forages. Annu Rev Nutr. 1985;5:391-409. [3927948 ]