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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.
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.*).
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