A plecomacrolide antibiotic
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Concanamycin A

Item No. 11050

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(1S,2R,3S)-3-[(2R,4R,5S,6R)-4-[[4-O-(aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]tetrahydro-2-hydroxy-5-methyl-6-(1E)-1-propen-1-yl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one
CAS Number
80890-47-7
Synonyms
  • Antibiotic X 4357B
  • NSC 674620
  • X 4357B
Molecular Formula
C46H75NO14
Formula Weight
866.1
Purity
≥95%
Formulation (Request formulation change)
A solution in acetonitrile
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMSO: SolubleMethanol: Soluble
SMILES
C[C@H](/C=C(C)/C=C1\OC)[C@@H](O)[C@@H](CC)[C@@H](O)[C@H](C)C/C(C)=C\C=C\[C@H](OC)[C@@]([C@@H](C)[C@@H](O)[C@H](C)[C@@](O)(C[C@@H](O[C@@]2([H])C[C@@H](O)[C@H](OC(N)=O)[C@@H](C)O2)[C@@H]3C)O[C@@H]3/C=C/C)([H])OC1=O
InChi Code
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
InChi Key
DJZCTUVALDDONK-LNFFOTJESA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Concanamycin A is a plecomacrolide antibiotic that has been found in Streptomyces.1 It is active against S. cerevisiae, S. sake, A. citri, P. citrinum, and P. oryzae (MICs = <0.39, <0.39, <0.39, 1.56, and 25 μg/ml, respectively). Concanamycin A inhibits vacuolar H+-ATPase (V-ATPase; EC50 = ~2.1-2.3 μM).2 It also decreases perforin levels in CD8+ OE4 cytotoxic T lymphocytes (CTLs).3 Concanamycin A (100 μM) inhibits concanavalin A-induced thymidine incorporation by 99% in isolated mouse splenic lymphocytes.1 It also prevents influenza virus entry into MDCK cells when used at a concentration of 0.8 μM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kinashi, H., Someno, K., and Sakahguchi, K. Isolation and characterization of concanamycins A, B and C. J. Antibiot. (Tokyo) 37(11), 1333-1343 (1984).

    2. Johnson, R.M., Allen, C., Melman, S.D., et al. Identification of inhibitors of V-ATPase pumps in yeast by HTS flow cytometry. Anal. Biochem. 398(2), 203-211 (2010).

    3. Kataoka, T., Takaku, K., Magae, J., et al. Acidification is essential for maintaining the structure and function of lytic granules of CTL. Effect of concanamycin A, an inhibitor of vacuolar type H+-ATPase, on CTL-mediated cytotoxicity. J. Immunol. 153(9), 3938-3947 (1994).

    4. Guinea, R., and Carrasco, L. Requirement for vacuolar proton-ATPase activity during entry of influenza virus into cells. J. Virol. 69(4), 2306-2312 (1995).