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

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ChEBI Name 8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide
ChEBI ID CHEBI:65363
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H22O6
Net Charge 0
Average Mass 322.35300
Monoisotopic Mass 322.14164
InChI InChI=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
InChIKey RWFXDGCFFQYKOB-CYYZGTNASA-N
SMILES [H][C@]12OC(=O)C(=C)[C@]1([H])[C@H](C[C@@](C)(O)[C@]1([H])C=C[C@@](C)(O)[C@]21[H])OC(C)=O
Metabolite of Species Details
Chrysanthemum boreale (NCBI:txid344871) Found in stem (BTO:0001300). See: PubMed
Chrysanthemum boreale (NCBI:txid344871) Found in leaf (BTO:0000713). 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 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 γ-lactone (CHEBI:37581)
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)
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 Number Type Source
18892294 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
18983901 PubMed citation Europe PMC
Last Modified
29 July 2013