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.

CHEBI:145556 CHEBI:145556
CHEBI:22702 CHEBI:22702
CHEBI:24079 CHEBI:24079
CHEBI:33853 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

Equivalent identifiers for this same structure in other resources.

beilstein:72665
cas:1397-94-0
cas:642-15-9
kegg.compound:C11339
metacyc.compound:CPD-5744
pdb-ccd:AY1

Activity roles

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

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: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.

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.