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CHEBI:65365 - 1-O-acetyl-4R,6S-britannilactone

Default Structure
ChEBI IDCHEBI:65365
ChEBI Name1-O-acetyl-4R,6S-britannilactone
Stars
ASCII Name1-O-acetyl-4R,6S-britannilactone
DefinitionA sesquiterpene lactone that is (3aS,4R,7aR)-3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one with a methylidene at position C-3, a hydroxy at C-4, a methyl at C-6, and a (2S)-5-(acetyloxy)pentan-2-yl group at position C-5. A natural product found in Inula britannica var chinensis and Inula japonica.
Last Modified21 February 2013
DownloadsMolfile
FormulaC17H24O5
Net Charge0
Average Mass308.374
Monoisotopic Mass308.16237
SMILES[H][C@@]12CC(C)=C([C@H](C)CCCOC(C)=O)[C@@H](O)[C@]1([H])C(=C)C(=O)O2
InChIInChI=1S/C17H24O5/c1-9(6-5-7-21-12(4)18)14-10(2)8-13-15(16(14)19)11(3)17(20)22-13/h9,13,15-16,19H,3,5-8H2,1-2,4H3/t9-,13-,15-,16-/m1/s1
InChIKeyQKUFZFLZBUSEHN-BYRYDROYSA-N
Species of MetaboliteComponentSourceComments
Inula japonica (ncbitaxon:453958) - DOI (10.1016/S0031-9422(00)90813-6)
Microtropis japonica (ncbitaxon:1089418) flower (BTO:0000469) PubMed (14969344)
Roles Classification
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
1-O-acetyl-4R,6S-britannilactone (CHEBI:65365) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
1-O-acetyl-4R,6S-britannilactone (CHEBI:65365) has role metabolite (CHEBI:25212)
1-O-acetyl-4R,6S-britannilactone (CHEBI:65365) is a acetate ester (CHEBI:47622)
1-O-acetyl-4R,6S-britannilactone (CHEBI:65365) is a organic heterobicyclic compound (CHEBI:27171)
1-O-acetyl-4R,6S-britannilactone (CHEBI:65365) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(4R)-4-[(3aS,4S,7aR)-4-hydroxy-6-methyl-3-methylidene-2-oxo-2,3,3a,4,7,7a-hexahydro-1-benzofuran-5-yl]pentyl acetate
Registry NumbersSources
Reaxys:11296086Reaxys
Citations