CHEBI:66090 - 3-O-methyl-isosecotanapartholide

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ChEBI Name 3-O-methyl-isosecotanapartholide
ChEBI ID CHEBI:66090
ChEBI ASCII Name 3-O-methyl-isosecotanapartholide
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H20O5
Net Charge 0
Average Mass 292.32700
Monoisotopic Mass 292.13107
InChI InChI=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
InChIKey YMBVLYVGHGDKHO-WHOFXGATSA-N
SMILES CO[C@H]1CC(=O)C([C@H]2OC(=O)C(=C)[C@@H]2CCC(C)=O)=C1C
Metabolite of Species Details
Tanacetum cilicicum (IPNI:252274-1) See: DOI
Artemisia iwayomogi (NCBI:txid265784) See: PubMed
Roles Classification
Biological Role(s): 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).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
4845668 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
12735688 PubMed citation Europe PMC
Last Modified
04 March 2013