trans-cis-nepetalactone (CHEBI:7519)

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ChEBI Name	trans-cis-nepetalactone

ChEBI ID	CHEBI:7519

ChEBI ASCII Name	trans-cis-nepetalactone

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C10H14O2

Net Charge

Average Mass

166.220

Monoisotopic Mass

166.09938

InChI

InChI=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

InChIKey

ZDKZHVNKFOXMND-ZQARSLAVSA-N

SMILES

[C@]12([C@]([C@H](CC1)C)(C(OC=C2C)=O)[H])[H]

Metabolite of Species	Details
Nepeta parnassica (IPNI:452640-1)	Found in aerial part (BTO:0001658). See: PubMed
Nepeta rtanjensis (IPNI:452698-1)	See: DOI
Nepeta cataria (NCBI:txid39347)	See: PubMed
Nepeta racemosa (NCBI:txid54731)	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. antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.

Application(s):	insect repellent An insecticide that acts as a repellent to insects.

ChEBI Ontology
Outgoing	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	Sources
(+)-(4aS,7S,7aS)-nepetalactone	ChemIDplus
(+)-trans,cis-nepetalactone	ChemIDplus
(4aα,7α,7aβ)-5,6,7,7a-tetrahydro-4,7-dimethylcyclopenta[c]pyran-1(4aH)-one	ChEBI
(4aS,7S,7aS)-nepetalactone	ChemIDplus
4aα,7α,7aβ-nepetalactone	ChEBI
E,Z-nepetalactone	ChemIDplus
epinepetalactone	ChemIDplus
isonepetalactone	ChemIDplus
nepetalactone trans-cis-form	KEGG COMPOUND
trans,cis-nepetalactone	ChemIDplus

Registry Number	Type	Source
17257-15-7	CAS Registry Number	ChemIDplus

Last Modified

14 August 2019