bigelovin (CHEBI:69337)

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ChEBI Name	bigelovin

ChEBI ID	CHEBI:69337

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

Download	Molfile XML SDF

Formula

C17H20O5

Net Charge

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

InChIKey

DCNRYQODUSSOKC-MMLVVLEOSA-N

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. immunomodulator 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.

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)

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 acetate	ChemIDplus

Last Modified

09 January 2014