Antimycin A4 - Moligand™, ≥98% , CAS No.27220-59-3

CAS: 27220-59-3 Cat. No.: A329337 Molecular Weight: 506.54 EC Number: 248-343-7

GRADE & PURITY Moligand™, ≥98%

Synonyms

Antimycin A4 (7CI,9CI) | 8X60D5011V | Butyric acid, N-ester with N-(7-butyl-8-hydroxy-4,9-dimethyl-2,6-dioxo-1,6-dioxonan-3-yl)-3-formamidosalicylamide | 8-Butyl-3-(3-formamido-2-hydroxybenzamido)-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl butyrate | J-0167

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Antimycin A4 is one of the derivatives in the antimycin family, a group of macrolides produced by the bacterium Streptomyces. This compound is notable for its role as a potent inhibitor of the mitochondrial electron transport chain, specifically targeting Complex III (cytochrome bc1 complex). Its mechanism of action involves binding to the Q_i site of Complex III, which effectively blocks the transfer of electrons from ubiquinol to cytochrome c, thereby halting the production of ATP and inducing a rapid increase in the production of reactive oxygen species (ROS) within the cell. This specific inhibition plays a crucial role in research focused on cellular respiration and energy metabolism, making Antimycin A4 a valuable tool for scientists studying mitochondrial dysfunctions and the regulation of oxidative stress. In addition to its use in basic biochemical studies, Antimycin A4 has been employed in ecological studies to assess the impact of mitochondrial inhibitors on aquatic organisms, thereby contributing to environmental assessments of water systems. Its ability to induce ROS production has also made it a candidate for studying the cellular responses to oxidative stress, including the activation of antioxidant defenses and signaling pathways related to cell survival and apoptosis. Through these varied applications, Antimycin A4 has helped advance our understanding of both environmental biology and fundamental cellular processes.

Specifications

Synonyms

Antimycin A4 (7CI, 9CI) | 8X60D5011V | Butyric acid, N-ester with N-(7-butyl-8-hydroxy-4, 9-dimethyl-2, 6-dioxo-1, 6-dioxonan-3-yl)-3-formamidosalicylamide | 8-Butyl-3-(3-formamido-2-hydroxybenzamido)-2, 6-dimethyl-4, 9-dioxo-1, 5-dioxonan-7-yl butyrate | J-0167

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CCC
• IUPAC Name: [8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] butanoate
• InChIKey: GYANSQKXOLFAFP-UHFFFAOYSA-N
• INCHI: 1S/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)
• Isomeric SMILES: CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CCC
• Molecular Weight: 506.54
• Reaxy-Rn: 1277391
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1277391&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acylaminobenzoic acid and derivatives
• Alternative Parents: Alpha amino acid esters N-acyl-alpha amino acids and derivatives Salicylamides Tricarboxylic acids and derivatives Anilides Benzamides N-arylamides Benzoyl derivatives 1-hydroxy-4-unsubstituted benzenoids Fatty acid esters Vinylogous acids Secondary carboxylic acid amides Lactones Carboxylic acid esters Oxacyclic compounds Organic oxides Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-amino acid ester - Acylaminobenzoic acid or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Salicylamide - Salicylic acid or derivatives - Benzamide - Anilide - Tricarboxylic acid or derivatives - Benzoyl - N-arylamide - 1-hydroxy-4-unsubstituted benzenoid - Fatty acid ester - Phenol - Fatty acyl - Vinylogous acid - Carboxamide group - Carboxylic acid ester - Lactone - Secondary carboxylic acid amide - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic oxide - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 506.500 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 506.226 Da
• Monoisotopic Mass: 506.226 Da
• Topological Polar Surface Area: 157.000 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 789.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 5
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1