An antifungal and antitrypanosomal antibiotic
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Venturicidin A

Item No. 15377

Technical Information
Formal Name
(1R,5S,6R,8R,9E,11R,15E,17R)-11-[[3-O-(aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1-hydroxy-5-[(1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxooctyl]-6,8,16,18-tetramethyl-4,21-dioxabicyclo[15.3.1]heneicosa-9,15,18-trien-3-one
CAS Number
33538-71-5
Synonyms
  • Aabomycin A1
Molecular Formula
C41H67NO11
Formula Weight
Purity
≥95%
A lyophilisate
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC1=CC[C@](CC(O[C@]([H])([C@@H](C[C@H]([C@@H]([C@@H](C(CC)=O)C)O)C)C)[C@@H]2C)=O)(O[C@@]1(/C(C)=C\CCC[C@@]([H])(O[C@@]([H])(C[C@H]3OC(N)=O)O[C@@H]([C@H]3O)C)/C=C/[C@@H](C2)C)[H])O
InChi Code
InChI=1S/C41H67NO11/c1-10-32(43)29(8)36(45)26(5)20-28(7)38-27(6)19-23(2)15-16-31(50-35-21-33(51-40(42)47)37(46)30(9)49-35)14-12-11-13-24(3)39-25(4)17-18-41(48,53-39)22-34(44)52-38/h13,15-17,23,26-31,33,35-39,45-46,48H,10-12,14,18-22H2,1-9H3,(H2,42,47
InChi Key
HHQKNFDAEDTRJK-KXQVSFSQSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Venturicidin A is a macrolide antibiotic isolated from strains of Streptomyces.1 It is active against fungi in the genus Venturia which cause apple scab, as well as other fungi, but not against higher plants.1 Venturicidin A is also cytotoxic against trypanosomes (IC50 = 120-540 ng/ml) while being more than 25,000 times less effective against mammalian cells.2 It inhibits bacterial and mitochondrial ATP synthases.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rhodes, A., Fantes, K.H., Boothroyd, B., et alVenturicidin: A new antifungal antibiotic of potential use in agriculture. Nature 192, 952-954 (1961).

    2. Otoguro, K., Ishiyama, A., Namatame, M., et alSelective and potent in vitro antitrypanosomal activities of ten microbial metabolites. J. Antibiot. (Tokyo) 61(6), 372-378 (2008).

    3. Perlin, D.S., Latchney, L.R., and Senior, A.E. Inhibition of Escherichia coli H+-ATPase by venturicidin, oligomycin and ossamycin. Biochim. Biophys. Acta 807(3), 238-244 (1985).

    4. Matsuno-Yagi, A., and Hatefi, Y. Studies on the mechanism of oxidative phosphorylation. ATP synthesis by submitochondrial particles inhibited at F0 by venturicidin and organotin compounds. The Journal of Biological Chemisty 268(9), 6168-6173 (1993).