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CHEBI:65955 - gelomulide K

ChEBI IDCHEBI:65955
ChEBI Namegelomulide K
Stars
DefinitionAn 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.
Last Modified7 February 2013
DownloadsMolfile
FormulaC22H28O5
Net Charge0
Average Mass372.461
Monoisotopic Mass372.19367
SMILES[H][C@@]12C[C@@]3([H])OC(=O)C(C)=C3[C@@]3([H])O[C@@]13CC[C@]1([H])C(C)(C)C=C[C@@H](OC(C)=O)[C@@]21C
InChIInChI=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
InChIKeyIWHCUIYQYFOMEF-FBERYXRISA-N
Species of MetaboliteComponentSourceComments
Gelonium aequoreum (IPNI:349172-1) leaf (BTO:0000713) PubMed (17714747)
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)
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 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)
gelomulide K (CHEBI:65955) is a γ-lactone (CHEBI:37581)
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-olideChEBI
Registry NumbersSources
Reaxys:15836693Reaxys
Citations