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Antimycin A information


Antimycin A
Names
Preferred IUPAC name
(2R,3S,6S,7R,8R)-3-(3-Formamido-2-hydroxybenzamido)-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl 3-methylbutanoate
Other names
Fintrol
Identifiers
CAS Number
  • 642-15-9 Antimycin A1 checkY
  • 1397-94-0 (Antimycin A), 116095-18-2 (Antimycin A1b)
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:22584 checkY
ChEMBL
  • ChEMBL211501 checkY
ChemSpider
  • 14246 checkY
ECHA InfoCard 100.162.279 Edit this at Wikidata
MeSH Antimycin+A
PubChem CID
  • 14957
UNII
  • 8771CCP8LT checkY
CompTox Dashboard (EPA)
  • DTXSID9032325 Edit this at Wikidata
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 checkY
    Key: UIFFUZWRFRDZJC-SBOOETFBSA-N checkY
  • 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 548.633 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Acute toxic
GHS labelling:
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H301, H311, H331
Precautionary statements
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Antimycin A (more exactly Antimycin A1b) is a secondary metabolite produced by Streptomyces bacteria[1] and a member of a group of related compounds called antimycins. Antimycin A is classified as an extremely hazardous substance in the United States, as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[2]

  1. ^ Neft N, Farley TM (March 1972). "Conditions influencing antimycin production by a Streptomyces species grown in chemically defined medium". Antimicrob. Agents Chemother. 1 (3): 274–6. doi:10.1128/aac.1.3.274. PMC 444205. PMID 4558141.
  2. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)

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Antimycin A

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Antimycin A (more exactly Antimycin A1b) is a secondary metabolite produced by Streptomyces bacteria and a member of a group of related compounds called...

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Antimycin

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Antimycins are produced as secondary metabolites by Streptomyces bacteria, a soil bacteria. These specialized metabolites likely function to kill neighboring...

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Superoxide

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Dioxygenyl, O+2 Antimycin A – used in fishery management, this compound produces large quantities of this free radical. Paraquat – used as a herbicide, this...

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Rainbow trout

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populations. This can be done by poisoning rivers with chemicals such as antimycin or rotenone which have been declared safe in the U.S. by the Environmental...

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Thenoyltrifluoroacetone

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inhibitor of respiration was by A. L. Tappel in 1960. Tappel had the (erroneous) idea that inhibitors like antimycin and alkyl hydroxyquinoline-N-oxide...

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CYC1

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purification of cytochrome c1 from mitochondrial Complex III. Reconstitution of antimycin-insensitive electron transfer with the iron-sulfur protein and cytochrome...

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Streptomyces

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previously identified Streptomyces sp. SirexAA-E. Antimycin A – Chemical compound produced by Streptomyces used as a piscicide Geosmin – Chemical compound responsible...

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EPA list of extremely hazardous substances

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Amphetamine Aniline Aniline, 2,4,6-trimethyl- Antimony pentafluoride Antimycin A ANTU (Alpha-Naphthylthiourea) Arsenic pentoxide Arsenous oxide Arsenous...

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Oxidative phosphorylation

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while cyanide and azide react with the oxidised form. An antibiotic, antimycin A, and British anti-Lewisite, an antidote used against chemical weapons...

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Asian swamp eel

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rotenone and antimycin A) that are transmitted across the gill membrane may not be effective. Serial pesticide dilutions of antimycin-A were tested and...

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Electron transport chain

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When electron transfer is reduced (by a high membrane potential or respiratory inhibitors such as antimycin A), Complex III may leak electrons to molecular...

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Piscicide

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Examples of piscicides include rotenone, saponins, TFM, niclosamide and Antimycin A (Fintrol). Historically, fishing techniques of indigenous people around...

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Rotenone

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combination with antimycin A (an electron transport chain Complex III inhibitor), oligomycin (an ATP synthase inhibitor) and FCCP (a mitochondrial uncoupler)...

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Myxothiazol

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Electron Transfer from Ubiquinol to Cytochrome by the Combined Action of Antimycin and Myxothiazol". FEBS Letters. 136 (1): 19–24. doi:10.1016/0014-5793(81)81206-9...

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UQCRH

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complex subunit 6, mitochondrial is a protein that in humans is encoded by the UQCRH gene. Its gene product is a subunit of the respiratory chain protein...

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UQCRC1

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complex subunit 1, mitochondrial is a protein that in humans is encoded by the UQCRC1 gene. Its gene product is a subunit of the respiratory chain protein...

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Blastmycin

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FUKUHARA, K; MIYAIRI, N; YONEHARA, H; UMEZAWA, H (March 1957). "Blastmycin, a new antibiotic from Streptomyces sp". The Journal of Antibiotics. 10 (2):...

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Histotoxic hypoxia

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interrupt the mitochondrial electron transport chain (e.g., rotenone, antimycin A) and produce effects on tissue oxygenation similar to that of cyanide...

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Mount Mazama

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respiration antimycin A. They also created small barriers to keep new trout from reaching Sun Creek. In 1999, Bull trout were considered a "threatened"...

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Urauchimycin

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Urauchimycins are antimycin antibiotics isolated from marine actinomycete. Imamura, N.; Nishijima, M.; Adachi, K.; Sano, H. (1993). "Novel antimycin antibiotics...

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Respiratory complex I

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inhibited by antimycin A". Journal of Neurochemistry. 148 (6): 731–745. doi:10.1111/jnc.14654. PMC 7086484. PMID 30582748. Stepanova A, Kahl A, Konrad C...

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Introduced trout in lake ecosystems

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lakes with a complex shoreline filled with woody debris. Two of the traditionally used piscidies in lake management are rotenone and antimycin. Chemical...

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Streptomyces lusitanus

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Yongxin; Qi, Shuhua; Huang, Xiangzhong; Qian, Peiyuan (22 March 2012). "Two Antimycin A Analogues from Marine-Derived Actinomycete Streptomyces lusitanus". Marine...

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UQCRFS1

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purification of cytochrome c1 from mitochondrial Complex III. Reconstitution of antimycin-insensitive electron transfer with the iron-sulfur protein and cytochrome...

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Phialophora fastigiata

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extract from Halacsya sendtneri, a flowering plant in the family Boraginaceae. The fungus is also susceptible to antimycins produced by Streptomyces species...

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Edward Slater

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certain inhibitors of oxidative phosphorylation acting at different sites (antimycin on electron transport, oligomycin on the coupling between electron transport...

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C16orf86

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Smith MJ, Simco BA, Warren CO (December 1975). "Comparative effects of antimycin A on isolated mitochondria of channel catfish (Ictalurus punctatus) and...

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