linoleic acid

CHEBI:17351 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

Linoleic acid is a polyunsaturated omega-6 fatty acid. Linoleic acid has been found to have antibacterial activity, particularly in inhibiting the growth of Gram-positive bacterial species. — PMID:19956944

Classification

antibacterial free fatty acidsARO:3003956

Strictly broader compounds or drug classes this molecule belongs to.

antibacterial free fatty acids ARO:3003956

Chemical structure

Computed structure properties
Molecular formula	C18H32O2
Charge	0
Average mass	280.452 Da
Monoisotopic mass	280.24023 Da
Source	ChEBI
InChIKey	OYHQOLUKZRVURQ-HZJYTTRNSA-N

SMILES

CCCCC/C=C\C/C=C\CCCCCCCC(=O)O

InChI

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

Also called

Linoleate (EXACT_SYNONYM)— aro
Linolic acid (EXACT_SYNONYM)— aro
Telfairic acid (EXACT_SYNONYM)— aro

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.

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
ARO	`ARO:3003959`	linoleic acid	`antibioticmech:aro-36bd42c165`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

bacterial cytoplasmic membrane MEMBRANE ATTACKED_COMPONENT

Growth, radiolabel incorporation, lipid uptake, glycerol-auxotroph, and permeability experiments associated free linoleic acid with a surfactant effect on the bacterial membrane. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1979-08 (retrieved 2026-09-02).

Staphylococcus aureus NCBITaxon:1280; strain NCTC 8325

PMID:93615 (Primary compound- and strain-specific study; supports membrane attack without claiming a protein-binding target.)

Mechanism summary

Mode of action: MEMBRANE_DISRUPTION host shared target — CURATOR: PMID:93615 linked growth inhibition of Staphylococcus aureus NCTC 8325 to increased bacterial-membrane permeability and supported a surfactant action of free linoleic acid. The record does not generalize that single-strain mechanism to every bacterium.

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

1 observations · Browse all observations · Complete record (JSON.gz)

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Staphylococcus aureus NCBITaxon:1280	ACTIVE	—	—	Growth inhibition accompanied by a bacterial-membrane permeability increase; the abstract does not report an MIC.	NCTC 8325	—	Evidence Page data (JSON.gz)

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
farAB	ARO:3003960	not organism-specific	—	ARO:3003960 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003959 (linoleic acid); database assertion, not a primary citation.)

Record-level evidence

PMID:93615 (Primary antibacterial mechanism and activity study.)
PMID:10925024 (Primary antibacterial activity study of isolated linoleic acid.)
PMID:10447892 (Primary study supporting farAB-mediated fatty-acid efflux resistance.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO)
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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified the exact ChEBI structure and ARO antibacterial classification; added a strain-scoped membrane-disruption mechanism, molecular component, and qualitative activity observation; checked primary support for the existing farAB resistance assertion.

Provenance

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

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