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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22339355https://www.ncbi.nlm.nih.gov/pubmed/24367419 | https://www.ncbi.nlm.nih.gov/pubmed/20080599 | https://www.ncbi.nlm.nih.gov/pubmed/22442197 | https://www.ncbi.nlm.nih.gov/pubmed/22493009Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8784423
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22339355https://www.ncbi.nlm.nih.gov/pubmed/24367419 | https://www.ncbi.nlm.nih.gov/pubmed/20080599 | https://www.ncbi.nlm.nih.gov/pubmed/22442197 | https://www.ncbi.nlm.nih.gov/pubmed/22493009
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8784423
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
Sources: https://pubs.usgs.gov/ifc/039/report.pdf
Curator's Comment: Known to be CNS penetrant in rats, fish. Human data not available
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25019929http://www.newmexicotu.org/Antimycin%20Summary.pdf
Curator's Comment: Antimycin A1 was first isolated during the 1940’s, and its molecular structure determined a few years later.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3720 |
29.5 µM [Ki] | ||
Target ID: CHEMBL361 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423 |
|||
Target ID: CHEMBL366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423 |
|||
Target ID: CHEMBL613767 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8784423 |
|||
Target ID: CHEMBL613064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7726490 |
|||
Target ID: P10415 Gene ID: 596.0 Gene Symbol: BCL2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11175751 |
|||
Target ID: Q07817 Gene ID: 598.0 Gene Symbol: BCL2L1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11175751 |
|||
Target ID: CHEMBL1671612 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22339355
Antimycin A1 inhibits ACL (ATP Citrate Lyase) against the substrate citrate with Ki 29.5 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:12:08 GMT 2025
by
admin
on
Mon Mar 31 23:12:08 GMT 2025
|
| Record UNII |
75G3NMU1TS
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |