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CHEBI:65956 - gelomulide M

ChEBI IDCHEBI:65956
ChEBI Namegelomulide M
Stars
DefinitionAn abietane diterpenoid that is ent-abieta-2(3),13(15)-diene-16,12-olide substituted by β-acetoxy groups at positions 1 and 7 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
FormulaC24H30O7
Net Charge0
Average Mass430.497
Monoisotopic Mass430.19915
SMILES[H][C@@]12C[C@@]3([H])OC(=O)C(C)=C3[C@@]3([H])O[C@@]13[C@@H](OC(C)=O)C[C@]1([H])C(C)(C)C=C[C@@H](OC(C)=O)[C@@]21C
InChIInChI=1S/C24H30O7/c1-11-19-14(30-21(11)27)9-16-23(6)15(22(4,5)8-7-17(23)28-12(2)25)10-18(29-13(3)26)24(16)20(19)31-24/h7-8,14-18,20H,9-10H2,1-6H3/t14-,15-,16+,17-,18+,20-,23-,24-/m1/s1
InChIKeyZHVJRNZAMURVAT-UGFIOAGRSA-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 M (CHEBI:65956) has role antineoplastic agent (CHEBI:35610)
gelomulide M (CHEBI:65956) has role metabolite (CHEBI:25212)
gelomulide M (CHEBI:65956) is a abietane diterpenoid (CHEBI:36762)
gelomulide M (CHEBI:65956) is a acetate ester (CHEBI:47622)
gelomulide M (CHEBI:65956) is a epoxide (CHEBI:32955)
gelomulide M (CHEBI:65956) is a organic heteropentacyclic compound (CHEBI:38164)
gelomulide M (CHEBI:65956) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(1β,5β,7β,9β,10α,12β,14β)-16-oxo-8,14:12,16-diepoxyabieta-2,13(15)-diene-1,7-diyl diacetate
Synonym  Source
1β,7β-diacetoxy-8β,14β-epoxy-ent-abieta-2(3),13(15)-diene-16,12-olideChEBI
Registry NumbersSources
Reaxys:15836698Reaxys
Citations