cis-trans-nepetalactone (CHEBI:7518)

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ChEBI Name	cis-trans-nepetalactone

ChEBI ID	CHEBI:7518

ChEBI ASCII Name	cis-trans-nepetalactone

Definition	A cyclopentapyran that is (4aS,7aR)-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,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties.

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

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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-NBEYISGCSA-N

SMILES

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

Roles Classification
Biological Role(s):	pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. insect attractant A chemical that attracts insects. analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. 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):	analgesic An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. insect repellent An insecticide that acts as a repellent to insects.

ChEBI Ontology
Outgoing	cis-trans-nepetalactone (CHEBI:7518) has role analgesic (CHEBI:35480) cis-trans-nepetalactone (CHEBI:7518) has role antibacterial agent (CHEBI:33282) cis-trans-nepetalactone (CHEBI:7518) has role antifungal agent (CHEBI:35718) cis-trans-nepetalactone (CHEBI:7518) has role insect attractant (CHEBI:24850) cis-trans-nepetalactone (CHEBI:7518) has role insect repellent (CHEBI:71692) cis-trans-nepetalactone (CHEBI:7518) has role pheromone (CHEBI:26013) cis-trans-nepetalactone (CHEBI:7518) has role plant metabolite (CHEBI:76924) cis-trans-nepetalactone (CHEBI:7518) is a cyclopentapyran (CHEBI:38606) cis-trans-nepetalactone (CHEBI:7518) is a iridoid monoterpenoid (CHEBI:50563)

IUPAC Name

(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one

Synonyms	Sources
(+)-(4aS,7S,7aR)-nepetalactone	ChEBI
(+)-cis,trans-nepetalactone	MetaCyc
(4aS)-5,6,7,7aα-tetrahydro-4,7α-dimethylcyclopenta[c]pyran-1(4aH)-one	ChEBI
(4aS,7S,7aR)-nepetalactone	ChemIDplus
4aα,7α,7aα-nepetalactone	ChemIDplus
cis,trans-nepetalactone	ChEBI
cis-trans-nepetalactone	UniProt
nepetalactone	ChemIDplus
nepetalactone cis-trans-form	KEGG COMPOUND

Last Modified

14 August 2019