oligomycin A

CHEBI:28285 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

An oligomycin with formula C45H74011. An inhibitor of mitochondrial F1FO ATP synthase that induces apoptosis in a variety of cell types and exhibits antifungal, antitumour, and nematicidal activities, but its clinical application has been limited by poor solubility in water and other biocompatible solvents. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

oligomycin CHEBI:25675
Label unavailable CHEBI:37205
Label unavailable CHEBI:46640
antibiotic antifungal agent CHEBI:86478

Chemical structure

Computed structure properties
Molecular formula	C45H74O11
Charge	0
Average mass	791.076 Da
Monoisotopic mass	790.52311 Da
Source	ChEBI
InChIKey	MNULEGDCPYONBU-AWJDAWNUSA-N

SMILES

CC[C@H]1/C=C/C=C/C[C@@H](C)[C@H](O)[C@@](C)(O)C(=O)[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@@H](C)[C@H](O)[C@@H](C)/C=C/C(=O)O[C@@H]2[C@H](C)[C@H](CC1)O[C@]1(CC[C@H](C)[C@H](C[C@@H](C)O)O1)[C@H]2C

InChI

InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31-,32-,33-,34-,35-,36-,38+,40+,41+,42-,44+,45-/m0/s1

Also called

(1R,4E,5'S,6S,6'S,7R,8S,10R,11R,12S,14R,15S,16R,18E,20E,22R,25S,27R,28S,29R)-22-ethyl-7,11,14,15-tetrahydroxy-6'-[(2R)-2-hydroxypropyl]-5',6,8,10,12,14,16,28,29-nonamethyl-3',4',5',6'-tetrahydro-3H,9H,13H-spiro[2,26-dioxabicyclo[23.3.1]nonacosa-4,18,20-triene-27,2'-pyran]-3,9,13-trione (EXACT_SYNONYM)— chebi
Oligomycin A (EXACT_SYNONYM)— chebi
RP-32705 (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.

antimicrobial agent CHEBI:33281
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:28285`	oligomycin A	`antibioticmech:chebi-b9f3fc663d`	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.

mitochondrial F_O ATP synthase c-ring PROTEIN_COMPLEX DIRECT_BINDING_TARGET

A 1.9-angstrom oligomycin-bound c10-ring crystal structure and a 3.8-angstrom cryo-EM structure of the full enzyme in a lipid bilayer directly defined the inhibited state. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2012-08; 2018-04 (retrieved 2026-09-02).

Saccharomyces cerevisiae NCBITaxon:4932

Organism-specific examples
Protein	Gene	Organism	Entry
ATP synthase subunit 9, mitochondrial `UniProtKB:P61829` Proton-translocating F_O c-ring subunit (Subunit 9 / Atp9) bound at the essential carboxyl-protonation face in the S. cerevisiae c10-ring oligomycin crystal structure (PMID:22869738, PDB 4F4S; S288c reference strain context).	OLI1	Saccharomyces cerevisiae (strain ATCC 204508 / S288c) `NCBITaxon:559292`	REVIEWED

PMID:22869738 (Primary oligomycin-c-ring crystal structure (DOI:10.1073/pnas.1207912109).)
PMID:29650704 (Primary full ATP-synthase cryo-EM study with oligomycin.)

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — CURATOR: PMID:22869738 reports a 1.9-angstrom crystal structure of oligomycin bound across two neighboring subunit-c molecules in the yeast mitochondrial ATP-synthase c-ring, explaining blockade of proton-coupled ATP synthesis. PMID:29650704 confirms the inhibited state in the full membrane complex by cryo-EM.

Record-level evidence

PMID:22869738 (Primary direct-binding structural study.)
PMID:29650704 (Primary full-complex structural study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antifungal class; curator-confirmed ATP-synthesis inhibition and added the directly bound mitochondrial ATP-synthase c-ring with two structural studies.
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated Saccharomyces cerevisiae S288c mitochondrial ATP synthase subunit 9 / OLI1 (P61829) UniProtKB protein example on the PRIMARY_LITERATURE mitochondrial F_O ATP synthase c-ring molecular target.

Provenance

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

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