CHEBI:27860 - castanospermine

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ChEBI Name castanospermine
ChEBI ID CHEBI:27860
Definition A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41729, CHEBI:3459, CHEBI:23050
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Formula C8H15NO4
Net Charge 0
Average Mass 189.20900
InChI InChI=1S/C8H15NO4/c10-4-1-2-9-3-5(11)7(12)8(13)6(4)9/h4-8,10-13H,1-3H2/t4-,5-,6+,7+,8+/m0/s1
InChIKey JDVVGAQPNNXQDW-TVNFTVLESA-N
SMILES [H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O
Metabolite of Species Details
Castanospermum australe (NCBI:24962) See: DOI
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
anti-HIV-1 agent
An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
EC 3.2.1.* (glycosidase) inhibitor
An EC 3.2.* (glycosylase) inhibitor that interferes with the action of any glycosidase (i.e. enzymes hydrolysing O- and S-glycosyl compounds, EC 3.2.1.*).
Application(s): anti-HIV-1 agent
An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing castanospermine (CHEBI:27860) has role anti-HIV-1 agent (CHEBI:64947)
castanospermine (CHEBI:27860) has role anti-inflammatory agent (CHEBI:67079)
castanospermine (CHEBI:27860) has role EC 3.2.1.* (glycosidase) inhibitor (CHEBI:52424)
castanospermine (CHEBI:27860) has role metabolite (CHEBI:25212)
castanospermine (CHEBI:27860) is a indolizidine alkaloid (CHEBI:38511)
IUPAC Name
(1S,6S,7R,8R,8aR)-octahydroindolizine-1,6,7,8-tetrol
Synonyms Sources
(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine ChEBI
(1S-(1α,6β,7α,8β,8αβ))-octahydro-1,6,7,8-indolizinetetrol ChEBI
1,6,7,8-tetrahydroxyoctahydroindolizine ChEBI
Castanospermine KEGG COMPOUND
CASTANOSPERMINE PDBeChem
castinospermine ChEBI
Database Links Databases
C00002028 KNApSAcK
C02256 KEGG COMPOUND
Castanospermine Wikipedia
CTS PDBeChem
KR20070061879 Patent
MX2009004170 Patent
US5837709 Patent
View more database links
Registry Numbers Types Sources
3588654 Reaxys Registry Number Reaxys
79831-76-8 CAS Registry Number KEGG COMPOUND
79831-76-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20552113 PubMed citation CiteXplore
22647882 PubMed citation CiteXplore
Last Modified
28 July 2014