CAS 27220-59-3

antimycin A4

Description:

Antimycin A4 is a natural antibiotic compound that belongs to the class of antimycin antibiotics, which are produced by certain species of Streptomyces. It is characterized by its ability to inhibit mitochondrial respiration by blocking the electron transport chain, specifically at complex III, which is crucial for ATP production. This inhibition leads to a decrease in cellular energy levels, making antimycin A4 a potent agent in biochemical research and potential therapeutic applications. The compound is typically a dark-colored solid and is soluble in organic solvents such as methanol and ethanol, but has limited solubility in water. Antimycin A4 exhibits antifungal and antibacterial properties, and its mechanism of action has made it a valuable tool in studying cellular respiration and metabolic processes. However, due to its toxicity, careful handling and usage are required in laboratory settings. Its structural complexity includes multiple functional groups that contribute to its biological activity and interaction with cellular components.

Formula: C₂₅H₃₄N₂O₉

InChI: InChI=1/C25H34N2O9/c1-5-7-10-17-22(36-19(29)9-6-2)15(4)35-25(33)20(14(3)34-24(17)32)27-23(31)16-11-8-12-18(21(16)30)26-13-28/h8,11-15,17,20,22,30H,5-7,9-10H2,1-4H3,(H,26,28)(H,27,31)

SMILES: CCCCC1C(C(C)OC(=O)C(C(C)OC1=O)N=C(c1cccc(c1O)N=CO)O)OC(=O)CCC

Synonyms:

• 8-Butyl-3-(3-formamido-2-hydroxybenzamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butyrate
• 8-Butyl-3-({[3-(Formylamino)-2-Hydroxyphenyl]Carbonyl}Amino)-2,6-Dimethyl-4,9-Dioxo-1,5-Dioxonan-7-Yl Butanoate (Non-Preferred Name)
• Antimycin A₄
• Butyric acid, N-ester with N-(7-butyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,6-dioxonan-3-yl)-3-formamidosalicylamide
• Antimycin A4
• Butyric acid 8-butyl-3-[(3-formylamino-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl ester
• 8-Butyl-3-[[3-(formylamino)-2-hydroxybenzoyl]amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonane-7-yl=butyrate
• DISCONTINUED, offer A697508

Antimycin A4

CAS: 27220-59-3

Antimycin A4, the most polar in the antimycin A antibiotic complex, inhibits ATP-citrate lyase (Ki=64.8 μM) and blocks mitochondrial respiration.

Formula: C₂₅H₃₄N₂O₉

Color and Shape: Solid

Molecular weight: 506.552

Ref: TM-T37498