antimycin A

CHEBI:2762 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison. — 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:145556
Label unavailable CHEBI:22702
Label unavailable CHEBI:24079
Label unavailable CHEBI:33853

Chemical structure

Computed structure properties
Charge
Source	ChEBI
InChIKey	UIFFUZWRFRDZJC-SBOOETFBSA-N

SMILES

[H]C(=O)Nc1cccc(C(=O)N[C@@H]2C(=O)O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@@H](CCCCCC)C(=O)O[C@@H]2C)c1O

InChI

InChI=1S/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34)/t17-,18+,20-,23+,25+/m1/s1

Also called

(2R,3S,6S,7R,8R)-3-[(3-formamido-2-hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate (EXACT_SYNONYM)— chebi
Antimycin A1 (EXACT_SYNONYM)— chebi
Antipiricullin (EXACT_SYNONYM)— chebi
Fintrol (EXACT_SYNONYM)— chebi
Virosin (EXACT_SYNONYM)— chebi
antimycin A1b (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.

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:2762`	antimycin A	`antibioticmech:chebi-2f92a93e11`	2026-08-30

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — Assigned from ChEBI role CHEBI:25355 (mitochondrial respiratory-chain inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Streptomyces sp. NCBITaxon:889487 strain S4	BGC0000958	Enzymatic assays; Gene expression correlated with compound production; Heterologous expression; Knock-out studies compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'antimycin' joined by exact Standard InChIKey.	PMID:21857911 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

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
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · 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 (antimycin A) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces sp.)