CHEBI:9367 - swainsonine

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ChEBI Name swainsonine
ChEBI ID CHEBI:9367
Definition An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C8H15NO3
Net Charge 0
Average Mass 173.20960
Monoisotopic Mass 173.105
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
InChIKey FXUAIOOAOAVCGD-WCTZXXKLSA-N
SMILES [H][C@]12[C@H](O)CCCN1C[C@@H](O)[C@H]2O
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor
An enzyme inhibitor that interferes with the action of mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase (EC 3.2.1.114), a key enzyme target in the development of anti-cancer therapies.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
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ChEBI Ontology
Outgoing swainsonine (CHEBI:9367) has role antineoplastic agent (CHEBI:35610)
swainsonine (CHEBI:9367) has role EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-α-mannosidase) inhibitor (CHEBI:65239)
swainsonine (CHEBI:9367) has role immunological adjuvant (CHEBI:50847)
swainsonine (CHEBI:9367) has role plant metabolite (CHEBI:76924)
swainsonine (CHEBI:9367) is a indolizidine alkaloid (CHEBI:38511)
INN Source
tridolgosir ChemIDplus
Synonym Source
Swainsonine KEGG COMPOUND
Manual Xrefs Databases
C00002075 KNApSAcK
C10173 KEGG COMPOUND
DB02034 DrugBank
SWA PDBeChem
Swainsonine Wikipedia
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Registry Numbers Types Sources
4175740 Reaxys Registry Number Reaxys
72741-87-8 CAS Registry Number KEGG COMPOUND
72741-87-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22281718 PubMed citation Europe PMC
22544335 PubMed citation Europe PMC
22578623 PubMed citation Europe PMC
Last Modified
28 July 2014