cis-cis-nepetalactol (CHEBI:144485)

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ChEBI Name	cis-cis-nepetalactol

ChEBI ID	CHEBI:144485

ChEBI ASCII Name	cis-cis-nepetalactol

Definition	A cyclopentapyran that is (4aR,7aS)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by a hydroxy group and at positions 4 and 7 by methyl groups (the 4aR,7S,7aS)-diastereomer.

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

Submitter	Kristian Axelsen

Supplier Information

Download	Molfile XML SDF

Formula

C10H16O2

Net Charge

Average Mass

168.236

Monoisotopic Mass

168.11503

InChI

InChI=1S/C10H16O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-11H,3-4H2,1-2H3/t6-,8-,9-,10?/m0/s1

InChIKey

OJGPEAXUHQRLNC-DJOKAMFZSA-N

SMILES

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

Metabolite of Species	Details
Nepeta mussinii (NCBI:txid54731)	See: PubMed

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.

ChEBI Ontology
Outgoing	cis-cis-nepetalactol (CHEBI:144485) has role pheromone (CHEBI:26013) cis-cis-nepetalactol (CHEBI:144485) has role plant metabolite (CHEBI:76924) cis-cis-nepetalactol (CHEBI:144485) is a cyclopentapyran (CHEBI:38606) cis-cis-nepetalactol (CHEBI:144485) is a iridoid monoterpenoid (CHEBI:50563) cis-cis-nepetalactol (CHEBI:144485) is a lactol (CHEBI:38131)

IUPAC Name

(4aR,7S,7aS)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-ol

Registry Number	Type	Source
185399-79-5	CAS Registry Number	ChEBI

Last Modified

16 August 2019