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CHEBI:65832 - (4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide

ChEBI IDCHEBI:65832
ChEBI Name(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide
Stars
ASCII Name(4betaH)-5alpha-hydroxy-8alpha-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6alpha-olide
DefinitionA guaiane sesquiterpenoid isolated from Elephantopus mollis and has been shown to exhibit cytotoxic activity.
Last Modified2 August 2013
DownloadsMolfile
FormulaC20H24O6
Net Charge0
Average Mass360.406
Monoisotopic Mass360.15729
SMILES[H][C@]12C(=C)C(=O)O[C@@H]1[C@]1(O)C(=C(C)C[C@@H]2OC(=O)/C(C)=C/C)C(=O)C[C@H]1C
InChIInChI=1S/C20H24O6/c1-6-9(2)18(22)25-14-7-10(3)16-13(21)8-11(4)20(16,24)17-15(14)12(5)19(23)26-17/h6,11,14-15,17,24H,5,7-8H2,1-4H3/b9-6+/t11-,14+,15-,17+,20-/m1/s1
InChIKeySKWQNPANRJEPQJ-JTOVZCNQSA-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)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) has functional parent tiglic acid (CHEBI:9592)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) has role antineoplastic agent (CHEBI:35610)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) has role metabolite (CHEBI:25212)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) is a enoate ester (CHEBI:51702)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) is a guaiane sesquiterpenoid (CHEBI:36744)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) is a organic heterotricyclic compound (CHEBI:26979)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) is a tertiary alcohol (CHEBI:26878)
(4βH)-5α-hydroxy-8α-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6α-olide (CHEBI:65832) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,9R,9aR,9bS)-9a-hydroxy-6,9-dimethyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-4-yl (2E)-2-methylbut-2-enoate
Registry NumbersSources
Reaxys:18556305Reaxys
Citations