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CHEBI:69337 - bigelovin

ChEBI IDCHEBI:69337
ChEBI Namebigelovin
Stars
DefinitionA 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.
Last Modified9 January 2014
DownloadsMolfile
FormulaC17H20O5
Net Charge0
Average Mass304.342
Monoisotopic Mass304.13107
SMILES[H][C@@]12C=CC(=O)[C@@]1(C)[C@@H](OC(C)=O)[C@]1([H])C(=C)C(=O)O[C@@]1([H])C[C@H]2C
InChIInChI=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
InChIKeyDCNRYQODUSSOKC-MMLVVLEOSA-N
Species of MetaboliteComponentSourceComments
Inula hupehensis (IPNI:225932-1) aerial part (BTO:0001658) PubMed (21894898) 95% aqueous EtOH extract of dried and powdered aerial parts
Roles Classification
Biological Roles:
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 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)
bigelovin (CHEBI:69337) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(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 acetateChemIDplus
Registry NumbersSources
Reaxys:1295049Reaxys
CAS:3668-14-2ChemIDplus
Citations