Antimycin A

Antimycin A

200px
Names
IUPAC name (2{R},3{S},6{S},7{R},8{R})-3-[(3-formamido- 2-hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo- 1,5-dioxonan-7-yl 3-methylbutanoate
Other names Fintrol
Identifiers
CAS Number	642-15-9 N
ChEBI	CHEBI:22584 Y
ChEMBL	ChEMBL211501 Y
ChemSpider	14246 Y
Jmol 3D model	Interactive image
MeSH	Antimycin+A
PubChem	14957
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 Y Key: UIFFUZWRFRDZJC-SBOOETFBSA-N Y InChI=1/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 Key: UIFFUZWRFRDZJC-SBOOETFBBB
SMILES O=CNc1cccc(c1O)C(=O)N[C@@H]2C(=O)O[C@H]([C@H](OC(=O)CC(C)C)[C@H](C(=O)O[C@@H]2C)CCCCCC)C
Properties
Chemical formula	C28H40N2O9
Molar mass	548.63 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Antimycins are a group of secondary metabolites produced by Streptomyces bacteria.

Use

It is the active ingredient in Fintrol, a chemical piscicide (fish poison) used in fisheries management and in the catfish industry.

Mechanism of action

Antimycin A binds to the Qi site of cytochrome c reductase, thereby inhibiting the oxidation of ubiquinone in the Qi site thereby disrupting the Q-cycle of enzyme turn over. Cytochrome c reductase is a central enzyme in the electron transport chain of oxidative phosphorylation. The inhibition of this reaction disrupts the formation of the proton gradient across the inner membrane. The production of ATP is subsequently inhibited, as protons are unable to flow through the ATP synthase complex in the absence of a proton gradient. This inhibition also results in the formation of quantities of the toxic free radical superoxide.

It has also been found to inhibit the cyclic electron flow within photosynthetic systems along the proposed ferredoxin quinone reductase pathway.

Fungus-growing attine ants have been shown to use antimycins - produced by symbiotic Streptomyces bacteria - in their fungiculture, to inhibit non-cultivar (i.e. pathogenic) fungi. One research group studying these symbiotic Streptomyces bacteria recently identified the biosynthetic gene cluster for antimycins, which was unknown despite the compounds themselves being identified 60 years ago. Antimycins are synthesised by a hybrid polyketide synthase (PKS)/non-ribosomal peptide synthase (NRPS).