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CHEBI:66089 - isosecotanapartholide

Default Structure
ChEBI IDCHEBI:66089
ChEBI Nameisosecotanapartholide
Stars
DefinitionA sesquiterpene lactone isolated from Artemisia rutifolia and Artemisia iwayomogi and has been shown to inhibit nitric oxide synthase.
Last Modified4 March 2013
DownloadsMolfile
FormulaC15H18O5
Net Charge0
Average Mass278.304
Monoisotopic Mass278.11542
SMILESC=C1C(=O)O[C@H](C2=C(C)[C@@H](O)CC2=O)[C@H]1CCC(C)=O
InChIInChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h10-11,14,17H,2,4-6H2,1,3H3/t10-,11-,14-/m0/s1
InChIKeyXXYRTFCLQHKIDU-MJVIPROJSA-N
Species of MetaboliteComponentSourceComments
Artemisia iwayomogi (ncbitaxon:265784) - PubMed (12735688)
Artemisia rutifolia (ncbitaxon:205374) - DOI (10.1016/0031-9422(86)80021-8)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
ChEBI Ontology
Outgoing Relation(s)
isosecotanapartholide (CHEBI:66089) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
isosecotanapartholide (CHEBI:66089) has role metabolite (CHEBI:25212)
isosecotanapartholide (CHEBI:66089) is a butan-4-olide (CHEBI:22950)
isosecotanapartholide (CHEBI:66089) is a enone (CHEBI:51689)
isosecotanapartholide (CHEBI:66089) is a methyl ketone (CHEBI:51867)
isosecotanapartholide (CHEBI:66089) is a secondary alcohol (CHEBI:35681)
isosecotanapartholide (CHEBI:66089) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(4S,5S)-5-[(3S)-3-hydroxy-2-methyl-5-oxocyclopent-1-en-1-yl]-3-methylidene-4-(3-oxobutyl)dihydrofuran-2(3H)-one
Registry NumbersSources
Reaxys:6521695Reaxys
Citations