alantolactone (CHEBI:2540)

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ChEBI Name	alantolactone

ChEBI ID	CHEBI:2540

Definition	A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H20O2

Net Charge

Average Mass

232.31810

Monoisotopic Mass

232.14633

InChI

InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1

InChIKey

PXOYOCNNSUAQNS-AGNJHWRGSA-N

SMILES

[H][C@@]12C[C@@]3(C)CCC[C@H](C)C3=C[C@]1([H])C(=C)C(=O)O2

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	alantolactone (CHEBI:2540) has role antineoplastic agent (CHEBI:35610) alantolactone (CHEBI:2540) has role apoptosis inducer (CHEBI:68495) alantolactone (CHEBI:2540) has role plant metabolite (CHEBI:76924) alantolactone (CHEBI:2540) is a naphthofuran (CHEBI:39270) alantolactone (CHEBI:2540) is a olefinic compound (CHEBI:78840) alantolactone (CHEBI:2540) is a sesquiterpene lactone (CHEBI:37667)

Incoming	5α-epoxyalantolactone (CHEBI:65856) has functional parent alantolactone (CHEBI:2540)

IUPAC Name

(3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one

Last Modified

04 February 2015