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

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ChEBI Name	1-O-acetyl-4R,6S-britannilactone

ChEBI ID	CHEBI:65365

ChEBI ASCII Name	1-O-acetyl-4R,6S-britannilactone

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C17H24O5

Net Charge

Average Mass

308.36950

Monoisotopic Mass

308.16237

InChI

InChI=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

InChIKey

QKUFZFLZBUSEHN-BYRYDROYSA-N

SMILES

[H][C@@]12CC(C)=C([C@H](C)CCCOC(C)=O)[C@@H](O)[C@]1([H])C(=C)C(=O)O2

Metabolite of Species	Details
Microtropis japonica (NCBI:txid1089418)	Found in flower (BTO:0000469). See: PubMed
Inula japonica (NCBI:txid453958)	See: DOI

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.

ChEBI Ontology
Outgoing	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 Number	Type	Source
11296086	Reaxys Registry Number	Reaxys

Last Modified

21 February 2013