igalan (CHEBI:66068)

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ChEBI Name	igalan

ChEBI ID	CHEBI:66068

Definition	A 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.

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/c1-6-15(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

InChIKey

IFASGTOWHLMHEZ-BHPKHCPMSA-N

SMILES

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

Metabolite of Species	Details
Eupatorium quadrangulare (IPNI:100785-2)	See: DOI
Inula grandis Schrenk (IPNI:225901-1)	Found in root (BTO:0001188). See: KHIM PRIR SOEDIN, 1970, 6, 508
Liatris platylepis (IPNI:230618-1)	See: DOI
Stevia polyphylla (IPNI:251515-1)	See: DOI
Critonia quadrangularis (IPNI:69565-2)	See: DOI
Rudbeckia laciniata (NCBI:txid52310)	Found in root (BTO:0001188). See: DOI
Inula helenium (NCBI:txid55635)	Found in root (BTO:0001188). See: PubMed

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

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

ChEBI Ontology
Outgoing	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-olide	ChEBI

Registry Number	Type	Source
5267066	Reaxys Registry Number	Reaxys

Citation	Type	Source
12392098	PubMed citation	Europe PMC

Last Modified

27 February 2013

General Comment
2012-07-27	KHIM PRIR SOEDIN, 1970, 6, 508