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Octahydroindolizine-1,2,8-triol

HCID 5363
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

Standard SMILES
OC1CN2CCCC(O)C2C1O
InChIKey
FXUAIOOAOAVCGD-UHFFFAOYSA-N
Molecular formula
C8H15NO3
Average molar mass
173.21 g/mol

Overview

octahydroindolizine-1,2,8-triol has been reported in Oxytropis, Astragalus oxyphysus, and Swainsona galegifolia with data available.

Names & identifiers

Preferred name
Octahydroindolizine-1,2,8-triol
IUPAC
1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol

Names & synonyms

octahydroindolizine-1,2,8-triol1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triolRefChem:366780Locoweed toxinOctahydro-1,2,8-indolizinetriol hydrochloride8,8a-DiepiswainsonineNSC652469orb3054152orb3179982SCHEMBL2267754(-)-(1S,2R,8R,8aR)-1,2,8-Trihydroxyoctahydroindolizine Hydrochloride1,2,8-trihydroxyoctahydroindolizine
Show more names
TN2344LS-13488DB-055672(1S,2R,8R,8aR)-1,2,8-Octahydroindolizidinetriol(1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-Octahydroindolizine- 1,2,8-triol

Database identifiers

PubChem CID
5363
Nikkaji
J2.116.288D

Properties

Computed structural propertiesFilling in

XLogP
-1.3
Topological polar surface area
63.9 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
176

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Health Effects · 1 item

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)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

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)

Signs and Symptoms · 1 item

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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Uses & manufacturing

UsesSwainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). (L1248, A3092)

Related reactions

1 records
New reaction record
HRID 1937438 reaction equation
HRID 1937438As reactantuspto-grants-2002_05

Compound notes

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