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.

CHEBI:38606 CHEBI:38606
CHEBI:50563 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

Equivalent identifiers for this same structure in other resources.

cas:17257-15-7
kegg.compound:C09792
knapsack:C00003092
lipidmaps:LMPR0102070014

Activity roles

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

CHEBI:33282 CHEBI:33282
CHEBI:35718 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.