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CHEBI:66068 - igalan

ChEBI IDCHEBI:66068
ChEBI Nameigalan
Stars
DefinitionA sesquiterpene lactone that is hexahydro-1-benzofuran-2(3H)-one substituted by a methyl group at position 6, methylene group at position 3, isopropenyl group at position 5 and a vinyl group at position 6. Isolated from Inula helenium and Rudbeckia laciniata, it exhibits antiproliferative activity.
Last Modified27 February 2013
DownloadsMolfile
FormulaC15H20O2
Net Charge0
Average Mass232.323
Monoisotopic Mass232.14633
SMILES[H][C@@]12C[C@](C)(C=C)[C@@H](C(=C)C)C[C@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C15H20O2/c1-6-15(5)8-13-11(7-12(15)9(2)3)10(4)14(16)17-13/h6,11-13H,1-2,4,7-8H2,3,5H3/t11-,12-,13-,15+/m1/s1
InChIKeyIFASGTOWHLMHEZ-BHPKHCPMSA-N
Species of MetaboliteComponentSourceComments
Liatris platylepis (IPNI:230618-1) - DOI (10.1016/0031-9422(79)80145-4)
Rudbeckia laciniata (ncbitaxon:52310) root (BTO:0001188) DOI (10.1016/S0031-9422(98)00251-9)
Inula helenium (ncbitaxon:55635) root (BTO:0001188) PubMed (12392098)
Eupatorium quadrangulare (IPNI:100785-2) - DOI (10.1016/S0031-9422(00)81100-0)
Inula grandis Schrenk (IPNI:225901-1) root (BTO:0001188) Article (KHIM PRIR SOEDIN, 1970, 6, 508)
Critonia quadrangularis (IPNI:69565-2) - DOI (10.1016/S0031-9422(00)81431-4)
Stevia polyphylla (IPNI:251515-1) - DOI (10.1016/0031-9422(88)80673-3)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
igalan (CHEBI:66068) has role antineoplastic agent (CHEBI:35610)
igalan (CHEBI:66068) has role metabolite (CHEBI:25212)
igalan (CHEBI:66068) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(3aR,5R,6R,7aR)-6-methyl-3-methylene-5-(prop-1-en-2-yl)-6-vinylhexahydro-1-benzofuran-2(3H)-one
Synonym  Source
1,3,11(13)-elematriene-8β,12-olideChEBI
Registry NumbersSources
Reaxys:5267066Reaxys
Citations