trans-cis-nepetalactone

CHEBI:7519 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:38606
Label unavailable CHEBI:50563

Chemical structure

Computed structure properties
Molecular formula	C10H14O2
Charge	0
Average mass	166.22 Da
Monoisotopic mass	166.09938 Da
Source	ChEBI
InChIKey	ZDKZHVNKFOXMND-ZQARSLAVSA-N

SMILES

[H][C@@]12C(=O)OC=C(C)[C@@]1([H])CC[C@@H]2C

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

Also called

(4aS,7S,7aS)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one (EXACT_SYNONYM)— chebi
(+)-(4aS,7S,7aS)-nepetalactone (EXACT_SYNONYM)— chebi
(+)-trans,cis-nepetalactone (EXACT_SYNONYM)— chebi
(4aS,7S,7aS)-nepetalactone (EXACT_SYNONYM)— chebi
(4aα,7α,7aβ)-5,6,7,7a-tetrahydro-4,7-dimethylcyclopenta[c]pyran-1(4aH)-one (EXACT_SYNONYM)— chebi
4aα,7α,7aβ-nepetalactone (EXACT_SYNONYM)— chebi
E,Z-nepetalactone (EXACT_SYNONYM)— chebi
epinepetalactone (EXACT_SYNONYM)— chebi
isonepetalactone (EXACT_SYNONYM)— chebi
nepetalactone trans-cis-form (EXACT_SYNONYM)— chebi
trans,cis-nepetalactone (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antibacterial agent CHEBI:33282
antifungal agent CHEBI:35718

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:7519`	trans-cis-nepetalactone	`antibioticmech:chebi-16270fd5b0`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (trans-cis-nepetalactone) · CultureMech · NaturalProductMech · PathwayMech · TraitMech