oleic acid

CHEBI:16196 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. Oleic acid is found to have antibacterial activity, particularly in inhibiting the growth of several Gram-positive bacterial species. — PMID:10447892

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	C18H34O2
Charge	0
Average mass	282.468 Da
Monoisotopic mass	282.25588 Da
Source	ChEBI
InChIKey	ZQPPMHVWECSIRJ-KTKRTIGZSA-N

SMILES

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

InChI

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

Also called

Cis-9-Octadecenoic acid (EXACT_SYNONYM)— aro
Cis-Oleic acid (EXACT_SYNONYM)— aro
Oleate (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:3003958`	oleic acid	`antibioticmech:aro-2b4430e8b1`	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.

group A streptococcal cytoplasmic membrane MEMBRANE ATTACKED_COMPONENT

Viable counts, radiolabel release and uptake, and electron microscopy supported loss of membrane integrity; the abstract does not identify the strain to species or collection accession. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 1979-12 (retrieved 2026-09-02).

group A Streptococcus; strain M type 6 strain

PMID:393631 (Primary mechanism study; supports membrane attack and does not imply a protein-binding target.)

Mechanism summary

Mode of action: MEMBRANE_DISRUPTION host shared target — CURATOR: PMID:393631 found rapid killing of an M type 6 group A streptococcus, loss of intracellular uridine label, ultrastructural surface damage, and loss of membrane integrity after oleic-acid exposure. The record keeps this mechanism scoped to that experiment.

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
group A Streptococcus	ACTIVE	—	—	Viable-count time course: 500 micrograms/mL oleic acid reduced viable counts by four orders of magnitude within five minutes.	M type 6 strain	—	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:3003958 (oleic acid); database assertion, not a primary citation.)

Record-level evidence

PMID:393631 (Primary bactericidal mechanism and activity study.)
PMID:10925024 (Primary antibacterial activity study of isolated oleic 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
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-02 · codex · LLM-assisted
Removed the false ARO synonym Elaidoic acid through a source-scoped seeder override after verifying it is the trans isomer; verified the remaining identity, structure, and class; added strain-scoped membrane mechanism, target, activity, and primary literature evidence.

Provenance

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

Explore across X-Mech: MediaIngredientMech (oleic acid) · CultureMech · NaturalProductMech · PathwayMech · TraitMech