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CHEBI:65833 - (4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide

ChEBI IDCHEBI:65833
ChEBI Name(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide
Stars
ASCII Name(4betaH)-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6alpha-olide
DefinitionA guaiane sesquiterpenoid isolated from Elephantopus mollis and has been shown to exhibit cytotoxic activity.
Last Modified2 August 2013
DownloadsMolfile
FormulaC20H22O5
Net Charge0
Average Mass342.391
Monoisotopic Mass342.14672
SMILES[H][C@]12C(=C)C(=O)O[C@@H]1C1=C(C(=C)C[C@@H]2OC(=O)/C(C)=C/C)C(=O)C[C@H]1C
InChIInChI=1S/C20H22O5/c1-6-9(2)19(22)24-14-8-11(4)15-13(21)7-10(3)16(15)18-17(14)12(5)20(23)25-18/h6,10,14,17-18H,4-5,7-8H2,1-3H3/b9-6+/t10-,14+,17-,18-/m1/s1
InChIKeyQFLXCTZTPACOEB-MIQTUIGVSA-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)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) has functional parent tiglic acid (CHEBI:9592)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) has role antineoplastic agent (CHEBI:35610)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) has role metabolite (CHEBI:25212)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) is a enoate ester (CHEBI:51702)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) is a enone (CHEBI:51689)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) is a guaiane sesquiterpenoid (CHEBI:36744)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) is a organic heterotricyclic compound (CHEBI:26979)
(4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide (CHEBI:65833) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,9R,9bS)-9-methyl-3,6-dimethylidene-2,7-dioxo-2,3,3a,4,5,6,7,8,9,9b-decahydroazuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:18556304Reaxys
Citations