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CHEBI:65834 - 2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide

ChEBI IDCHEBI:65834
ChEBI Name2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide
Stars
ASCII Name2,5-epoxy-2beta-hydroxy-8alpha-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6alpha-olide
DefinitionA guaiane sesquiterpenoid isolated from Elephantopus mollis and has been shown to exhibit cytotoxic activity.
Last Modified2 August 2013
DownloadsMolfile
FormulaC21H28O7
Net Charge0
Average Mass392.448
Monoisotopic Mass392.18350
SMILES[H][C@]12OC(=O)C(=C)[C@]1([H])[C@@H](OC(=O)/C(C)=C/C)CC(=C)C[C@]1(O)C[C@@](C)(OC)[C@@H]2O1
InChIInChI=1S/C21H28O7/c1-7-12(3)18(22)26-14-8-11(2)9-21(24)10-20(5,25-6)17(28-21)16-15(14)13(4)19(23)27-16/h7,14-17,24H,2,4,8-10H2,1,3,5-6H3/b12-7+/t14-,15+,16-,17+,20+,21+/m0/s1
InChIKeyPDFFFCDISRKSLI-KSIAICTFSA-N
Species of MetaboliteComponentSourceComments
Elephantopus mollis (ncbitaxon:318057)
stem (BTO:0001300) PubMed (18239317)
root (BTO:0001188) PubMed (18239317)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) has functional parent tiglic acid (CHEBI:9592)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) has role antineoplastic agent (CHEBI:35610)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) has role metabolite (CHEBI:25212)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) is a enoate ester (CHEBI:51702)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) is a guaiane sesquiterpenoid (CHEBI:36744)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) is a organic heterotricyclic compound (CHEBI:26979)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) is a tertiary alcohol (CHEBI:26878)
2,5-epoxy-2β-hydroxy-8α-(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6α-olide (CHEBI:65834) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,8R,10R,11R,11aS)-8-hydroxy-10-methoxy-10-methyl-3,6-dimethylidene-2-oxododecahydro-8,11-epoxycyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:11152426Reaxys
Citations