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CHEBI:66090 - 3-O-methyl-isosecotanapartholide

ChEBI IDCHEBI:66090
ChEBI Name3-O-methyl-isosecotanapartholide
Stars
ASCII Name3-O-methyl-isosecotanapartholide
DefinitionA sesquiterpene lactone that is isosecotanapartholide in which the hydroxy group at position 3 is replaced by a methoxy group. Isolated from Artemisia iwayomogi and Tanacetum cilicicum, it acts as an inhibitor of nitric oxide synthase.
Last Modified4 March 2013
DownloadsMolfile
FormulaC16H20O5
Net Charge0
Average Mass292.331
Monoisotopic Mass292.13107
SMILESC=C1C(=O)O[C@H](C2=C(C)[C@@H](OC)CC2=O)[C@H]1CCC(C)=O
InChIInChI=1S/C16H20O5/c1-8(17)5-6-11-9(2)16(19)21-15(11)14-10(3)13(20-4)7-12(14)18/h11,13,15H,2,5-7H2,1,3-4H3/t11-,13-,15-/m0/s1
InChIKeyYMBVLYVGHGDKHO-WHOFXGATSA-N
Species of MetaboliteComponentSourceComments
Artemisia iwayomogi (ncbitaxon:265784) - PubMed (12735688)
Tanacetum cilicicum (IPNI:252274-1) - DOI (10.1016/0031-9422(90)80039-J)
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)
3-O-methyl-isosecotanapartholide (CHEBI:66090) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
3-O-methyl-isosecotanapartholide (CHEBI:66090) has role metabolite (CHEBI:25212)
3-O-methyl-isosecotanapartholide (CHEBI:66090) is a butan-4-olide (CHEBI:22950)
3-O-methyl-isosecotanapartholide (CHEBI:66090) is a enone (CHEBI:51689)
3-O-methyl-isosecotanapartholide (CHEBI:66090) is a ether (CHEBI:25698)
3-O-methyl-isosecotanapartholide (CHEBI:66090) is a methyl ketone (CHEBI:51867)
3-O-methyl-isosecotanapartholide (CHEBI:66090) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(4S,5S)-5-[(3S)-3-methoxy-2-methyl-5-oxocyclopent-1-en-1-yl]-3-methylidene-4-(3-oxobutyl)dihydrofuran-2(3H)-one
Registry NumbersSources
Reaxys:4845668Reaxys
Citations