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CHEBI:65844 - 1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene

ChEBI IDCHEBI:65844
ChEBI Name1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene
Stars
ASCII Name1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene
DefinitionA sesquiterpenoid that is bisabola-2,10-diene substituted by a peroxy group between positions 2 and 10 (the 1S,4R,6R stereoisomer). Isolated from Artemisia stolonifera and Eupatorium rufescens, it exhibits antineoplastic and antiplasmodial activity.
Last Modified18 January 2013
DownloadsMolfile
FormulaC15H24O2
Net Charge0
Average Mass236.355
Monoisotopic Mass236.17763
SMILES[H][C@]1([C@@H](C)CCC=C(C)C)C[C@H]2OO[C@@H]1C=C2C
InChIInChI=1S/C15H24O2/c1-10(2)6-5-7-11(3)13-9-14-12(4)8-15(13)17-16-14/h6,8,11,13-15H,5,7,9H2,1-4H3/t11-,13+,14+,15+/m0/s1
InChIKeyLJPSCRDRIZSODI-ZGKBOVNRSA-N
Species of MetaboliteComponentSourceComments
Eupatorium rufescens (IPNI:206830-1) - PubMed (17252501)
Alpinia densibracteata (IPNI:871940-1) - DOI (10.1016/S0031-9422(96)00863-1)
Senecio selloi (ncbitaxon:462559) - PubMed (17252501)
Artemisia stolonifera (ncbitaxon:637488) aerial part (BTO:0001658) PubMed (10836741)
Artemisia selengensis (ncbitaxon:637485) - Article (J PHARMACOGN, 1993, 24, 107)
Roles Classification
Chemical Role:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
Biological Roles:
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antiplasmodial drug  An antiparasitic drug which is effective against Apicomplexan parasites in the genus Plasmodium. The genus contains over 200 species and includes those responsible for malaria.
ChEBI Ontology
Outgoing Relation(s)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) has parent hydride bisabolane (CHEBI:36480)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) has role antineoplastic agent (CHEBI:35610)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) has role antiplasmodial drug (CHEBI:64915)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) has role metabolite (CHEBI:25212)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) is a organic peroxide (CHEBI:25702)
1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65844) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(1S,4R,7R)-5-methyl-7-[(2S)-6-methylhept-5-en-2-yl]-2,3-dioxabicyclo[2.2.2]oct-5-ene
Registry NumbersSources
Reaxys:7746152Reaxys
Citations