CHEBI:65955 - gelomulide K

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ChEBI Name gelomulide K
ChEBI ID CHEBI:65955
Definition An abietane diterpenoid that is ent-abieta-2(3),13(15)-diene-16,12-olide substituted by a 1β-acetoxy group and a β-epoxy group across positions 8 and 14. Isolated from the leaves of Gelonium aequoreum, it exhibits moderate cytotoxicity against lung (A549), breast (MDAMB-231 and MCF7), and liver (HepG2) cancer cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H28O5
Net Charge 0
Average Mass 372.45470
Monoisotopic Mass 372.19367
InChI InChI=1S/C22H28O5/c1-11-17-13(26-19(11)24)10-15-21(5)14(6-9-22(15)18(17)27-22)20(3,4)8-7-16(21)25-12(2)23/h7-8,13-16,18H,6,9-10H2,1-5H3/t13-,14-,15+,16-,18-,21-,22+/m1/s1
InChIKey IWHCUIYQYFOMEF-FBERYXRISA-N
SMILES [H][C@@]12C[C@]3([H])[C@]4(CC[C@]5([H])C(C)(C)C=C[C@@H](OC(C)=O)[C@@]35C)O[C@]4([H])C1=C(C)C(=O)O2
Metabolite of Species Details
Gelonium aequoreum (IPNI:349172-1) 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 gelomulide K (CHEBI:65955) has role antineoplastic agent (CHEBI:35610)
gelomulide K (CHEBI:65955) has role metabolite (CHEBI:25212)
gelomulide K (CHEBI:65955) is a γ-lactone (CHEBI:37581)
gelomulide K (CHEBI:65955) is a abietane diterpenoid (CHEBI:36762)
gelomulide K (CHEBI:65955) is a acetate ester (CHEBI:47622)
gelomulide K (CHEBI:65955) is a epoxide (CHEBI:32955)
gelomulide K (CHEBI:65955) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name
(1β,5β,9β,10α,12β,14β)-16-oxo-8,14:12,16-diepoxyabieta-2,13(15)-dien-1-yl acetate
Synonym Source
1β-acetoxy-8β,14β-epoxy-ent-abieta-2(3),13(15)-diene-16,12-olide ChEBI
Registry Number Type Source
15836693 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17714747 PubMed citation Europe PMC
21641992 PubMed citation Europe PMC
Last Modified
07 February 2013