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CHEBI:144482 - cis-cis-nepetalactone

ChEBI IDCHEBI:144482
ChEBI Namecis-cis-nepetalactone
Stars
ASCII Namecis-cis-nepetalactone
DefinitionA cyclopentapyran that is (4aR,7aS)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aR,7S,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species.
Last Modified16 August 2019
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC10H14O2
Net Charge0
Average Mass166.220
Monoisotopic Mass166.09938
SMILES[H][C@@]12CC[C@H](C)[C@]1([H])C(=O)OC=C2C
InChIInChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8-,9-/m0/s1
InChIKeyZDKZHVNKFOXMND-XVYDVKMFSA-N
Species of MetaboliteComponentSourceComments
Nepeta nuda (IPNI:452615-1) - DOI (10.1016/S0031-9422(00)84709-3)
Nepeta x faassenii (ncbitaxon:39348) leaf (BTO:0000713) PubMed (16900434)
Nepeta persica (IPNI:452651-1) - PubMed (20433086) Detected in flower, leaf, stem and root.
Nepeta bornmuelleri (ncbitaxon:21339) aerial part (BTO:0001658) DOI (10.1080/10412905.2007.9699274)
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.
ChEBI Ontology
Outgoing Relation(s)
cis-cis-nepetalactone (CHEBI:144482) has role plant metabolite (CHEBI:76924)
cis-cis-nepetalactone (CHEBI:144482) is a cyclopentapyran (CHEBI:38606)
cis-cis-nepetalactone (CHEBI:144482) is a iridoid monoterpenoid (CHEBI:50563)
IUPAC Name 
(4aR,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
Synonyms  Source
(+)-cis,cis-nepetalactoneChemIDplus
(4aR,7S,7aS)-nepetalactoneChemIDplus
cis,cis-nepetalactoneChemIDplus
4aβ,7α,7aβ-nepetalactoneChemIDplus
(+)-(4aR,7S,7aS)-nepetalactoneChemIDplus
UniProt Name  Source
cis-cis-nepetalactoneUniProt
Manual XrefsDatabases
CPD-22360MetaCyc
C00010639KNApSAcK
Registry NumbersSources
CAS:21651-53-6ChemIDplus
CAS:21651-53-6NIST Chemistry WebBook
Citations