cis-cis-nepetalactone (CHEBI:144482)

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ChEBI Name	cis-cis-nepetalactone

ChEBI ID	CHEBI:144482

ChEBI ASCII Name	cis-cis-nepetalactone

Definition	A 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.

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

Submitter	Kristian Axelsen

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-XVYDVKMFSA-N

SMILES

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

Metabolite of Species	Details
Nepeta nuda (IPNI:452615-1)	See: DOI
Nepeta persica (IPNI:452651-1)	Detected in flower, leaf, stem and root. See: PubMed
Nepeta bornmuelleri (NCBI:txid21339)	Found in aerial part (BTO:0001658). See: DOI
Nepeta x faassenii (NCBI:txid39348)	Found in leaf (BTO:0000713). 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.

ChEBI Ontology
Outgoing	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

Last Modified

16 August 2019