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

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:
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)
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