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CHEBI:27860 - castanospermine

ChEBI IDCHEBI:27860
ChEBI Namecastanospermine
Stars
DefinitionA 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).
Secondary ChEBI IDsCHEBI:3459, CHEBI:23050, CHEBI:41729
Last Modified28 July 2014
DownloadsMolfile
FormulaC8H15NO4
Net Charge0
Average Mass189.211
Monoisotopic Mass189.10011
SMILES[H][C@]12[C@@H](O)CCN1C[C@H](O)[C@@H](O)[C@@H]2O
InChIInChI=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
InChIKeyJDVVGAQPNNXQDW-TVNFTVLESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Castanospermum australe (ncbitaxon:24962) - DOI (10.1016/0031-9422(81)85181-3)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.*).
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
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  Source
CastanospermineKEGG COMPOUND
CASTANOSPERMINEPDBeChem
castinospermineChEBI
(1S-(1α,6β,7α,8β,8αβ))-octahydro-1,6,7,8-indolizinetetrolChEBI
(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidineChEBI
1,6,7,8-tetrahydroxyoctahydroindolizineChEBI
Manual XrefsDatabases
C02256KEGG COMPOUND
CTSPDBeChem
MX2009004170Patent
KR20070061879Patent
US5837709Patent
CastanospermineWikipedia
C00002028KNApSAcK
Registry NumbersSources
Reaxys:3588654Reaxys
CAS:79831-76-8KEGG COMPOUND
CAS:79831-76-8ChemIDplus
Citations