CHEBI:69337 - bigelovin

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ChEBI Name bigelovin
Definition A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by methyl groups at positions 4a and 8, a methylidene group at position 3 and an acetoxy group at position 4. Isolated from Inula hupehensis, it exhibits antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H20O5
Net Charge 0
Average Mass 304.33770
Monoisotopic Mass 304.13107
InChI InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11+,12+,14-,15+,17+/m1/s1
SMILES C[C@@H]1C[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(C)=O)[C@@]2(C)[C@H]1C=CC2=O
Metabolite of Species Details
Inula hupehensis (IPNI:225932-1) Found in aerial part (BTO:0001658). 95% aqueous EtOH extract of dried and powdered aerial parts See: PubMed
Roles Classification
Biological Role(s): apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing bigelovin (CHEBI:69337) has role antineoplastic agent (CHEBI:35610)
bigelovin (CHEBI:69337) has role apoptosis inducer (CHEBI:68495)
bigelovin (CHEBI:69337) has role immunomodulator (CHEBI:50846)
bigelovin (CHEBI:69337) has role plant metabolite (CHEBI:76924)
bigelovin (CHEBI:69337) is a γ-lactone (CHEBI:37581)
bigelovin (CHEBI:69337) is a acetate ester (CHEBI:47622)
bigelovin (CHEBI:69337) is a cyclic ketone (CHEBI:3992)
bigelovin (CHEBI:69337) is a organic heterotricyclic compound (CHEBI:26979)
bigelovin (CHEBI:69337) is a sesquiterpene lactone (CHEBI:37667)
(3aR,4S,4aR,7aR,8R,9aS)-4a,8-dimethyl-3-methylidene-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl acetate
Synonym Source
6α,8α-dihydroxy-4-oxo-ambrosa-2,11(13)-dien-12-oic acid-12,8-lactone acetate ChemIDplus
Registry Numbers Types Sources
1295049 Reaxys Registry Number Reaxys
3668-14-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19107858 PubMed citation Europe PMC
21894898 PubMed citation Europe PMC
23231968 PubMed citation Europe PMC
24118350 PubMed citation Europe PMC
8657753 PubMed citation Europe PMC
Last Modified
09 January 2014