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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H40N2O9
Molecular Weight 548.6252
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANTIMYCIN A1B

SMILES

CCCCCC[C@@H]1[C@@H](OC(=O)CC(C)C)[C@H](C)OC(=O)[C@@H](NC(=O)C2=CC=CC(NC=O)=C2O)[C@@H](C)OC1=O

InChI

InChIKey=UIFFUZWRFRDZJC-SBOOETFBSA-N
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

HIDE SMILES / InChI

Molecular Formula C28H40N2O9
Molecular Weight 548.6252
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Antimycin A is widely used as a piscicide in the catfish farming industry (brandname Fintrol) and has potent killing activity against insects, nematodes and fungi. Antimycin A is a potent inhibitor of ubiquinol-cytochrome C oxidoreductase (complex III). By inhibiting cytochrome C reductase in the electron transport chain of mitochondria antimycin A halts respiration. It has been used to study the metabolic signature of RCD in human cultured skeletal muscle cells. The specific sites of reactive oxygen species (ROS) production in mitochondria isolated from skeletal muscle of chronic obstructive pulmonary disease and lung cancer patients, and its relationship with local oxidative stress induced by exercise have been studied using antimycin A as well. More recently, antimycin A has attracted attention as a potent and selective inhibitor of the mitochondrial anti-apoptotic proteins Bcl-2 and Bcl-xL which are over-produced in cancer cells resistant to apoptosis-inducing chemotherapy agents, so antimycin A may have a potential as anticancer drug for combination chemotherapy.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rats, fish. Human data not available

Originator

Curator's Comment: Antimycin A1 was first isolated during the 1940’s, and its molecular structure determined a few years later.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The regulation and biosynthesis of antimycins.
2013-11-19
Site of mitochondrial reactive oxygen species production in skeletal muscle of chronic obstructive pulmonary disease and its relationship with exercise oxidative stress.
2012-09
Mitochondrial reactive oxygen species and calcium uptake regulate activation of phagocytic NADPH oxidase.
2012-05-15
A plasma signature of human mitochondrial disease revealed through metabolic profiling of spent media from cultured muscle cells.
2010-01-26
The respiratory inhibitor antimycin A specifically binds Fe(III) ions and mediates utilization of iron by the halotolerant alga Dunaliella salina (Chlorophyta).
2004-02
Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3.
2001-02
UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02. I. Fermentation, isolation, and biological properties.
1996-07
Effects of atovaquone and other inhibitors on Pneumocystis carinii dihydroorotate dehydrogenase.
1995-02
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Antimycin A1 inhibits ACL (ATP Citrate Lyase) against the substrate citrate with Ki 29.5 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:12:08 GMT 2025
Edited
by admin
on Mon Mar 31 23:12:08 GMT 2025
Record UNII
75G3NMU1TS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTIMYCIN A1B
Common Name English
BUTANOIC ACID, 3-METHYL-, (2R,3S,6S,7R,8R)-3-((3-(FORMYLAMINO)-2-HYDROXYBENZOYL)AMINO)-8-HEXYL-2,6-DIMETHYL-4,9-DIOXO-1,5-DIOXONAN-7-YL ESTER
Preferred Name English
BUTANOIC ACID, 3-METHYL-, 3-((3-(FORMYLAMINO)-2-HYDROXYBENZOYL)AMINO)-8-HEXYL-2,6-DIMETHYL-4,9-DIOXO-1,5-DIOXONAN-7-YL ESTER, (2R-(2R*,3S*,6S*,7R*,8R*))-
Systematic Name English
Code System Code Type Description
CHEBI
2762
Created by admin on Mon Mar 31 23:12:08 GMT 2025 , Edited by admin on Mon Mar 31 23:12:08 GMT 2025
PRIMARY
CAS
116095-18-2
Created by admin on Mon Mar 31 23:12:08 GMT 2025 , Edited by admin on Mon Mar 31 23:12:08 GMT 2025
PRIMARY
PUBCHEM
14957
Created by admin on Mon Mar 31 23:12:08 GMT 2025 , Edited by admin on Mon Mar 31 23:12:08 GMT 2025
PRIMARY
FDA UNII
75G3NMU1TS
Created by admin on Mon Mar 31 23:12:08 GMT 2025 , Edited by admin on Mon Mar 31 23:12:08 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY