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CHEBI:7518 - cis-trans-nepetalactone

ChEBI IDCHEBI:7518
ChEBI Namecis-trans-nepetalactone
Stars
ASCII Namecis-trans-nepetalactone
DefinitionA 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.
Last Modified14 August 2019
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-NBEYISGCSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cinara pilicornis (ncbitaxon:506607) - PubMed (18166192)
Nepeta cataria (ncbitaxon:39347) leaf (BTO:0000713) PubMed (29091815)
Nepeta racemosa (ncbitaxon:54731) - PubMed (15974613)
Nepeta sibirica (ncbitaxon:180189) - PubMed (20307630)
Nepeta caesarea (IPNI:452314-1) - PubMed (9720633)
Roles Classification
Biological Roles:
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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.
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 attractant  A chemical that attracts insects.
Applications:
insect repellent  An insecticide that acts as a repellent to 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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
nepetalactone cis-trans-formKEGG COMPOUND
cis,trans-nepetalactoneChEBI
4aα,7α,7aα-nepetalactoneChemIDplus
nepetalactoneChemIDplus
(4aS)-5,6,7,7aα-tetrahydro-4,7α-dimethylcyclopenta[c]pyran-1(4aH)-oneChEBI
(4aS,7S,7aR)-nepetalactoneChemIDplus
UniProt Name  Source
cis-trans-nepetalactoneUniProt
Manual XrefsDatabases
C09791KEGG COMPOUND
C00003091KNApSAcK
LMPR0102070013LIPID MAPS
NepetalactoneWikipedia
CPD-15029MetaCyc
Registry NumbersSources
CAS:21651-62-7KEGG COMPOUND
CAS:21651-62-7ChemIDplus
CAS:21651-62-7NIST Chemistry WebBook
Citations