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CHEBI:2540 - alantolactone

ChEBI IDCHEBI:2540
ChEBI Namealantolactone
Stars
DefinitionA 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.
Last Modified4 February 2015
DownloadsMolfile
FormulaC15H20O2
Net Charge0
Average Mass232.323
Monoisotopic Mass232.14633
SMILES[H][C@@]12C[C@@]3(C)CCC[C@H](C)C3=C[C@]1([H])C(=C)C(=O)O2
InChIInChI=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
InChIKeyPXOYOCNNSUAQNS-AGNJHWRGSA-N
Species of MetaboliteComponentSourceComments
Inula helenium (ncbitaxon:55635) - PubMed (24996657)
Saussurea lappa (ncbitaxon:324593) - PubMed (25068579)
Roles Classification
Biological Roles:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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
Synonyms  Source
AlantolactoneKEGG COMPOUND
Elecampane camphorChemIDplus
Alant camphorChemIDplus
Inula camphorChemIDplus
EupatalChemIDplus
HelenineChemIDplus
Manual XrefsDatabases
C09289KEGG COMPOUND
C00012893KNApSAcK
LMPR0103190013LIPID MAPS
HMDB0035906HMDB
Registry NumbersSources
Reaxys:5266481Reaxys
CAS:546-43-0KEGG COMPOUND
CAS:546-43-0ChemIDplus
Citations