Antimycin A3

• CAT Number: I011419
• CAS Number: 522-70-3
• PubChem Substance ID: 245869
• Molecular Formula: C26H36N2O9
• Molecular Weight: 520.58
• Purity: ≥95%
• Synonyms: antimycin a3;ioxonan-3-yl)-3-formamidosalicylamide,stereoisomer;isovalericacid,n-esterwithn-(7-butyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,5-d;[2R-(2R*,3S*,6S*,7R*,8R*)]-8-butyl-3-(3-formamidosalicylamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl isoval
• Storage: -20°C
• Related CAS: 1362-89-6;11011-32-8
• IUPAC Name: [(2R,3S,6S,7R,8R)-8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
• InChI: InChI=1S/C26H36N2O9/c1-6-7-9-18-23(37-20(30)12-14(2)3)16(5)36-26(34)21(15(4)35-25(18)33)28-24(32)17-10-8-11-19(22(17)31)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32)/t15-,16+,18-,21+,23+/m1/s1
• InChIKey: PVEVXUMVNWSNIG-PDPGNHKXSA-N
• SMILES: CCCC[C@@H]1[C@H]([C@@H](OC(=O)[C@H]([C@H](OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C

Antimycin A3(Cat No.:I011419) is a naturally occurring antibiotic and mitochondrial electron transport inhibitor. It belongs to the antimycin class of compounds and is derived from the fermentation of certain Streptomyces bacteria. Antimycin A3 exerts its pharmacologic action by binding to complex III (cytochrome bc1 complex) in the mitochondrial respiratory chain, disrupting electron transfer and inhibiting oxidative phosphorylation. This disruption leads to a decrease in ATP synthesis and an accumulation of reactive oxygen species. Antimycin A3 is commonly employed as a research tool to investigate mitochondrial function, oxidative stress, and cellular metabolism. It is also used in agricultural settings to control plant pathogens and as a piscicide in fish management programs.

Reference

1.Yonehara H. & Takeuchi S. J. Studies on the chemical structure of blastmycin. Antibiotics Ser. A 11, 254 (1958).
2.Barrow, C.J., Oleynek, J.J., Marinelli, V., et al. Antimycins, inhibitors of ATP-<wbr style=”box-sizing: border-box;” />citrate lyase, from a Streptomyces sp. J. Antibiot. (Tokyo) 50(9), 729-733 (1997).
3.Takimoto, H., Machida, K., Ueki, M., et al. UK-<wbr style=”box-sizing: border-box;” />2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-<wbr style=”box-sizing: border-box;” />02 IV. Comparative studies of UK-<wbr style=”box-sizing: border-box;” />2A with antimycin A3 on cytotoxic activity and reactive oxygen species generation in LLC-<wbr style=”box-sizing: border-box;” />PK1 cells. J. Antibiot. (Tokyo) 52(5),480-484 (1999).