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CHEBI:81377 - (+)-nootkatone

ChEBI IDCHEBI:81377
ChEBI Name(+)-nootkatone
Stars
DefinitionA 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).
Last Modified4 September 2018
DownloadsMolfile
FormulaC15H22O
Net Charge0
Average Mass218.340
Monoisotopic Mass218.16707
SMILESC=C(C)[C@@H]1CCC2=CC(=O)C[C@@H](C)[C@]2(C)C1
InChIInChI=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
InChIKeyWTOYNNBCKUYIKC-JMSVASOKSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Citrus x paradisi (ncbitaxon:37656) - PubMed (16272746)
Callitropsis nootkatensis (ncbitaxon:85954) - PubMed (15962787)
Cyperus rotundus (ncbitaxon:512623) - PubMed (24704449)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
insect repellent  An insecticide that acts as a repellent to insects.
fragrance  A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
ChEBI Ontology
Outgoing Relation(s)
(+)-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
Synonym  Source
nootkatoneChEBI
UniProt Name  Source
(+)-nootkatoneUniProt
Manual XrefsDatabases
C17914KEGG COMPOUND
C00016987KNApSAcK
NootkatoneWikipedia
HMDB0013687HMDB
US2012045806Patent
Registry NumbersSources
CAS:4674-50-4KEGG COMPOUND
CAS:4674-50-4ChemIDplus
CAS:4674-50-4NIST Chemistry WebBook
Citations