CHEBI:2762 - antimycin A

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ChEBI Name antimycin A
ChEBI ID CHEBI:2762
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40908, CHEBI:22584
Supplier Information
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Formula C28H40N2O9
Net Charge 0
Average Mass 548.633
Monoisotopic Mass 548.27338
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
InChIKey UIFFUZWRFRDZJC-SBOOETFBSA-N
SMILES C1([C@H]([C@H](OC([C@@H]([C@H]([C@@H](O1)C)OC(CC(C)C)=O)CCCCCC)=O)C)NC(C2=C(C(=CC=C2)NC(=O)[H])O)=O)=O
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
mitochondrial respiratory-chain inhibitor

Application(s): piscicide
A substance which is poisonous to fish and is primarily used to eliminate dominant species of fish in water.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing antimycin A (CHEBI:2762) has role antifungal agent (CHEBI:35718)
antimycin A (CHEBI:2762) has role mitochondrial respiratory-chain inhibitor (CHEBI:25355)
antimycin A (CHEBI:2762) has role piscicide (CHEBI:167183)
antimycin A (CHEBI:2762) is a benzamides (CHEBI:22702)
antimycin A (CHEBI:2762) is a formamides (CHEBI:24079)
antimycin A (CHEBI:2762) is a macrodiolide (CHEBI:145556)
antimycin A (CHEBI:2762) is a phenols (CHEBI:33853)
IUPAC Name
(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
Synonyms Sources
Antimycin A1 KEGG COMPOUND
antimycin A1b ChEBI
Antipiricullin ChemIDplus
Fintrol ChemIDplus
Virosin ChemIDplus
Manual Xrefs Databases
AY1 PDBeChem
C11339 KEGG COMPOUND
CPD-5744 MetaCyc
View more database links
Registry Numbers Types Sources
1397-94-0 CAS Registry Number ChemIDplus
642-15-9 CAS Registry Number KEGG COMPOUND
642-15-9 CAS Registry Number ChemIDplus
642-15-9 CAS Registry Number ChemIDplus
72665 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
16819166 PubMed citation Europe PMC
29790043 PubMed citation Europe PMC
30914247 PubMed citation Europe PMC
31079230 PubMed citation Europe PMC
32662599 PubMed citation Europe PMC
Last Modified
13 January 2021