CHEBI:22584 - antimycin A

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ChEBI Name antimycin A
ChEBI ID CHEBI:22584
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.
Supplier Information
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Formula C28H40N2O9
Net Charge 0
Average Mass 548.62520
Monoisotopic Mass 548.273
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 [H]C(=O)Nc1cccc(C(=O)N[C@H]2[C@@H](C)OC(=O)[C@H](CCCCCC)[C@@H](OC(=O)CC(C)C)[C@H](C)OC2=O)c1O
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

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ChEBI Ontology
Outgoing antimycin A (CHEBI:22584) has role antifungal agent (CHEBI:35718)
antimycin A (CHEBI:22584) has role mitochondrial respiratory-chain inhibitor (CHEBI:25355)
antimycin A (CHEBI:22584) is a benzamides (CHEBI:22702)
antimycin A (CHEBI:22584) is a formamides (CHEBI:24079)
antimycin A (CHEBI:22584) is a lactone (CHEBI:25000)
antimycin A (CHEBI:22584) 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 Xref Database
C11339 KEGG COMPOUND
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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
72665 Beilstein Registry Number Beilstein
Last Modified
06 July 2015