CHEBI:81377 - (+)-nootkatone

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ChEBI Name (+)-nootkatone
ChEBI ID CHEBI:81377
Definition A sesquiterpenoid that is 4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one which is substituted by methyl groups at positions 4 and 4a, and by an isopropenyl group at position 6 (the 4R,4aS,6R stereoisomer).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H22O
Net Charge 0
Average Mass 218.335
Monoisotopic Mass 218.167
InChI InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1
InChIKey WTOYNNBCKUYIKC-JMSVASOKSA-N
SMILES [C@@]12(C(CC[C@H](C1)C(C)=C)=CC(C[C@H]2C)=O)C
Metabolite of Species Details
Citrus x paradisi (NCBI:txid37656) See: PubMed
Cyperus rotundus (NCBI:txid512623) See: PubMed
Callitropsis nootkatensis (NCBI:txid85954) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): fragrance
A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
insect repellent
An insecticide that acts as a repellent to insects.
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ChEBI Ontology
Outgoing (+)-nootkatone (CHEBI:81377) has role fragrance (CHEBI:48318)
(+)-nootkatone (CHEBI:81377) has role insect repellent (CHEBI:71692)
(+)-nootkatone (CHEBI:81377) has role plant metabolite (CHEBI:76924)
(+)-nootkatone (CHEBI:81377) is a carbobicyclic compound (CHEBI:36785)
(+)-nootkatone (CHEBI:81377) is a enone (CHEBI:51689)
(+)-nootkatone (CHEBI:81377) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
(4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
Synonyms Sources
(+)-nootkatone UniProt
nootkatone ChEBI
Manual Xrefs Databases
C00016987 KNApSAcK
C17914 KEGG COMPOUND
HMDB0013687 HMDB
Nootkatone Wikipedia
US2012045806 Patent
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Registry Numbers Types Sources
4674-50-4 CAS Registry Number KEGG COMPOUND
4674-50-4 CAS Registry Number ChemIDplus
4674-50-4 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11441443 PubMed citation Europe PMC
15962787 PubMed citation Europe PMC
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Last Modified
04 September 2018