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CHEBI:65363 - 8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide

ChEBI IDCHEBI:65363
ChEBI Name8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide
Stars
DefinitionA sesquiterpene lactone and an organic heterotricyclic compound that is 2,3,3a,4,5,6,6a,9,9a,9b-decahydroazuleno[4,5-b]furan substituted by an acetoxy group at position 4, hydroxy groups at positions 6 and 9, methyl groups at positions 6 and 9, a methylidene group at position 3 and an oxo group at position 2. It is a guaianolide isolated from Chrysanthemum boreale and has been shown to exhibit cytotoxic activity against human cancer cell lines.
Last Modified29 July 2013
DownloadsMolfile
FormulaC17H22O6
Net Charge0
Average Mass322.357
Monoisotopic Mass322.14164
SMILES[H][C@@]12C=C[C@@](C)(O)[C@]1([H])[C@@]1([H])OC(=O)C(=C)[C@]1([H])[C@@H](OC(C)=O)C[C@@]2(C)O
InChIInChI=1S/C17H22O6/c1-8-12-11(22-9(2)18)7-17(4,21)10-5-6-16(3,20)13(10)14(12)23-15(8)19/h5-6,10-14,20-21H,1,7H2,2-4H3/t10-,11+,12-,13+,14+,16-,17-/m1/s1
InChIKeyRWFXDGCFFQYKOB-CYYZGTNASA-N
Species of MetaboliteComponentSourceComments
Chrysanthemum boreale (ncbitaxon:344871)
leaf (BTO:0000713) PubMed (18983901)
stem (BTO:0001300) PubMed (18983901)
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)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) has role antineoplastic agent (CHEBI:35610)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) has role metabolite (CHEBI:25212)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) is a acetate ester (CHEBI:47622)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) is a organic heterotricyclic compound (CHEBI:26979)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) is a sesquiterpene lactone (CHEBI:37667)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) is a tertiary alcohol (CHEBI:26878)
8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (CHEBI:65363) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3aR,4S,6R,6aR,9R,9aS,9bS)-6,9-dihydroxy-6,9-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,6,6a,9,9a,9b-decahydroazuleno[4,5-b]furan-4-yl acetate
Registry NumbersSources
Reaxys:18892294Reaxys
Citations