Concanamycin A

• CAT Number: I010600
• CAS Number: 80890-47-7
• Molecular Formula: C46H75NO14
• Molecular Weight: 866.1
• Purity: ≥95%
• Synonyms: Alternative Name: Folimycin
• Target: Autophagy
• Solubility: Soluble in DMSO
• Appearance: White solid
• Storage: −20°C
• IUPAC Name: [(2R,3S,4R,6R)-6-[(2R,4R,5S,6R)-2-[(2S,3R,4S)-4-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl]-2-hydroxy-5-methyl-6-[(E)-prop-1-enyl]oxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] carbamate
• InChI: InChI=1S/C46H75NO14/c1-13-16-34-28(7)37(58-38-22-33(48)43(31(10)57-38)60-45(47)53)23-46(54,61-34)30(9)41(51)29(8)42-35(55-11)18-15-17-24(3)19-26(5)39(49)32(14-2)40(50)27(6)20-25(4)21-36(56-12)44(52)59-42/h13,15-18,20-21,26-35,37-43,48-51,54H,14,19,22-23H2,1-12H3,(H2,47,53)/b16-13+,18-15+,24-17+,25-20+,36-21-/t26-,27-,28-,29+,30+,31-,32+,33-,34-,35+,37-,38+,39+,40-,41-,42-,43-,46-/m1/s1
• InChIKey: DJZCTUVALDDONK-HQMSUKCRSA-N
• SMILES: CCC1C(C(CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C=CC)C)OC3CC(C(C(O3)C)OC(=O)N)O)O)O)OC)C)C)O

Concanamycin A（Cat No.:I010600）, also known as Antibiotic X 4357B, is a naturally occurring macrolide antibiotic that functions as a specific inhibitor of the vacuolar H+-ATPase (V-ATPase). V-ATPase is an enzyme complex that is responsible for acidifying intracellular compartments, and it plays a critical role in various physiological processes, including protein degradation, membrane trafficking, and ion transport. Concanamycin A binds to the V-ATPase complex and inhibits its activity, thereby disrupting acidification and causing various cellular effects.

Reference

The V-ATPase inhibitors concanamycin A and bafilomycin A lead to Golgi swelling in tobacco BY-2 cells. Robinson D.G. et al. , Protoplasma 2004, 224, 255. 

Concanamycin A, a powerful tool for characterization and estimation of contribution of perforin- and Fas-based lytic pathways in cell-mediated cytotoxicity. Kataoka T. et al. , J. Immunol. 1996, 156, 3678. 

Specific inhibitors of vacuolar type H(+)-ATPases induce apoptotic cell death. Nishihara T. et al. , Biochem. Biophys. Res. Commun. 1995, 212, 255. 

Folimycin (concanamycin A), a specific inhibitor of V-ATPase, blocks intracellular translocation of the glycoprotein of vesicular stomatitis virus before arrival to the Golgi apparatus. Muroi M. et al. , Cell Struct. Funct. 1993, 18, 139.