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

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ChEBI Name (4βH)-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6α-olide
ChEBI ID CHEBI:65833
ChEBI ASCII Name (4betaH)-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(5),10(14),11(13)-guaiatrien-12,6alpha-olide
Definition A guaiane sesquiterpenoid isolated from Elephantopus mollis and has been shown to exhibit cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H22O5
Net Charge 0
Average Mass 342.38570
Monoisotopic Mass 342.14672
InChI InChI=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
InChIKey QFLXCTZTPACOEB-MIQTUIGVSA-N
SMILES [H][C@@]12[C@H](CC(=C)C3=C([C@H](C)CC3=O)[C@H]1OC(=O)C2=C)OC(=O)C(\C)=C\C
Metabolite of Species Details
Elephantopus mollis (NCBI:txid318057) Found in stem (BTO:0001300). See: PubMed
Elephantopus mollis (NCBI:txid318057) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (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 γ-lactone (CHEBI:37581)
(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)
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 Number Type Source
18556304 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18239317 PubMed citation Europe PMC
Last Modified
02 August 2013