CHEBI:65845 - 1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene

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ChEBI Name 1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene
ChEBI ID CHEBI:65845
ChEBI ASCII Name 1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene
Definition A sesquiterpenoid that is bisabola-2,10-diene substituted by a peroxy group between positions 2 and 10 (the 1R,4S,6R stereoisomer). Isolated from Artemisia stolonifera and Eupatorium rufescens, it exhibits antineoplastic and antiplasmodial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB1257009, eMolecules:30316209, ZINC000000895297
Download Molfile XML SDF
Formula C15H24O2
Net Charge 0
Average Mass 236.34990
Monoisotopic Mass 236.17763
InChI InChI=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
InChIKey LJPSCRDRIZSODI-ATGSNQNLSA-N
SMILES [H][C@@]1(C[C@@H]2OO[C@H]1C=C2C)[C@@H](C)CCC=C(C)C
Metabolite of Species Details
Eupatorium rufescens (IPNI:206830-1) See: PubMed
Alpinia densibracteata (IPNI:871940-1) See: DOI
Senecio selloi (NCBI:txid462559) See: PubMed
Artemisia selengensis (NCBI:txid637485) See: J PHARMACOGN, 1993, 24, 107
Artemisia stolonifera (NCBI:txid637488) Found in aerial part (BTO:0001658). See: PubMed
Roles Classification
Chemical Role(s): oxidising agent
A substance that removes electrons from another reactant in a redox reaction.
(via peroxides )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) has parent hydride bisabolane (CHEBI:36480)
1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) has role antineoplastic agent (CHEBI:35610)
1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) has role antiplasmodial drug (CHEBI:64915)
1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) has role metabolite (CHEBI:25212)
1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) is a organic peroxide (CHEBI:25702)
1R,4S,6R-1,4-endoperoxy-bisabola-2,10-diene (CHEBI:65845) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
(1R,4S,7R)-5-methyl-7-[(2S)-6-methylhept-5-en-2-yl]-2,3-dioxabicyclo[2.2.2]oct-5-ene
Citations Types Sources
10836741 PubMed citation Europe PMC
17252501 PubMed citation Europe PMC
Last Modified
18 January 2013
General Comment
2012-07-27 J PHARMACOGN, 1993, 24, 107