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

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ChEBI Name	1S,4R,6R-1,4-endoperoxy-bisabola-2,10-diene

ChEBI ID	CHEBI:65844

ChEBI ASCII Name	1S,4R,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 1S,4R,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

Download	Molfile XML SDF

Formula

C15H24O2

Net Charge

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-ZGKBOVNRSA-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.

ChEBI Ontology
Outgoing	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 Number	Type	Source
7746152	Reaxys Registry Number	Reaxys

Last Modified

18 January 2013

General Comment
2012-07-27	J PHARMACOGN, 1993, 24, 107