CHEBI:6390 - laurenobiolide

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ChEBI Name laurenobiolide
ChEBI ID CHEBI:6390
Definition A germacranolide isolated from Laurus nobilis L. and which has been shown to exhibit allergenic activity.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H22O4
Net Charge 0
Average Mass 290.35420
Monoisotopic Mass 290.15181
InChI InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h7-8,14-16H,3,5-6,9H2,1-2,4H3/b10-8+,11-7+/t14-,15?,16?/m0/s1
InChIKey ORJVLIMAQARNOU-LXNAOKSISA-N
SMILES CC(=O)O[C@H]1\C=C(C)\CC\C=C(C)\CC2OC(=O)C(=C)C12
Roles Classification
Biological Role(s): allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing laurenobiolide (CHEBI:6390) has role allergen (CHEBI:50904)
laurenobiolide (CHEBI:6390) has role metabolite (CHEBI:25212)
laurenobiolide (CHEBI:6390) is a germacranolide (CHEBI:73011)
Incoming deacetyllaurenobiolide (CHEBI:55349) has functional parent laurenobiolide (CHEBI:6390)
IUPAC Name
[(4S,5E,9E)-6,10-dimethyl-3-methylidene-2-oxo-2,3,3a,4,7,8,11,11a-octahydrocyclodeca[b]furan-4-yl] acetate
Synonym Source
Laurenobiolide KEGG COMPOUND
Manual Xrefs Databases
C00003314 KNApSAcK
C09492 KEGG COMPOUND
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Registry Numbers Types Sources
35001-25-3 CAS Registry Number KEGG COMPOUND
7000904 Beilstein Registry Number Beilstein
7000904 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
6476889 PubMed citation Europe PMC
Last Modified
24 September 2014