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CHEBI:7519 - trans-cis-nepetalactone

ChEBI IDCHEBI:7519
ChEBI Nametrans-cis-nepetalactone
Stars
ASCII Nametrans-cis-nepetalactone
DefinitionA cyclopentapyran that is (4aS,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 4aS,7S,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It exhibits potent repellant activity against house dust mites and mosquitoes.
Last Modified14 August 2019
DownloadsMolfile
FormulaC10H14O2
Net Charge0
Average Mass166.220
Monoisotopic Mass166.09938
SMILES[H][C@@]12C(=O)OC=C(C)[C@@]1([H])CC[C@@H]2C
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-ZQARSLAVSA-N
Species of MetaboliteComponentSourceComments
Nepeta racemosa (ncbitaxon:54731) - PubMed (15974613)
Nepeta rtanjensis (IPNI:452698-1) - DOI ( 10.1016/j.indcrop.2017.02.027 )
Nepeta cataria (ncbitaxon:39347) - PubMed (21056438)
Nepeta parnassica (IPNI:452640-1) aerial part (BTO:0001658) PubMed (24449446)
Roles Classification
Biological Roles:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
Application:
insect repellent  An insecticide that acts as a repellent to insects.
ChEBI Ontology
Outgoing Relation(s)
trans-cis-nepetalactone (CHEBI:7519) has role antibacterial agent (CHEBI:33282)
trans-cis-nepetalactone (CHEBI:7519) has role antifungal agent (CHEBI:35718)
trans-cis-nepetalactone (CHEBI:7519) has role insect repellent (CHEBI:71692)
trans-cis-nepetalactone (CHEBI:7519) has role plant metabolite (CHEBI:76924)
trans-cis-nepetalactone (CHEBI:7519) is a cyclopentapyran (CHEBI:38606)
trans-cis-nepetalactone (CHEBI:7519) is a iridoid monoterpenoid (CHEBI:50563)
IUPAC Name 
(4aS,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one
Synonyms  Source
nepetalactone trans-cis-formKEGG COMPOUND
(+)-(4aS,7S,7aS)-nepetalactoneChemIDplus
(+)-trans,cis-nepetalactoneChemIDplus
trans,cis-nepetalactoneChemIDplus
(4aS,7S,7aS)-nepetalactoneChemIDplus
E,Z-nepetalactoneChemIDplus
Manual XrefsDatabases
C09792KEGG COMPOUND
C00003092KNApSAcK
LMPR0102070014LIPID MAPS
Registry NumbersSources
CAS:17257-15-7KEGG COMPOUND
CAS:17257-15-7ChemIDplus
Citations