A polyketide antibiotic that inhibits oxidoreductase
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Aureothin

Item No. 19463

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-methoxy-3,5-dimethyl-6-[(2R,4Z)-tetrahydro-4-[(2E)-2-methyl-3-(4-nitrophenyl)-2-propen-1-ylidene]-2-furanyl]-4H-pyran-4-one
CAS Number
2825-00-5
Synonyms
  • Antibiotic 74A
  • BRN 0058476
  • JA 2814K
  • Mycolutein
  • Strain 58 substance
Molecular Formula
C22H23NO6
Formula Weight
397.4
Purity
≥96%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: soluble
SMILES
CC(/C=C1CO[C@@H](C(OC(OC)=C2C)=C(C)C2=O)C\1)=C\C3=CC=C([N+]([O-])=O)C=C3
InChi Code
InChI=1S/C22H23NO6/c1-13(9-16-5-7-18(8-6-16)23(25)26)10-17-11-19(28-12-17)21-14(2)20(24)15(3)22(27-4)29-21/h5-10,19H,11-12H2,1-4H3/b13-9+,17-10-/t19-/m1/s1
InChi Key
GQKXCBCSVYJUMI-WACKOAQBSA-N
Origin
Bacterium/Streptomyces thioluteus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $290

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    5 mg

    $863

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    Product Description

    Aureothin is a natural nitroaryl-substituted polyketide that exhibits antitumor, antifungal, and insecticidal activities.1,2 It is a non-competitive inhibitor of NADH:ubiquinone oxidoreductase of bovine heart, N. crassa, and E. coli (IC50s = 0.07, 0.08, and 22 nmol/mg protein, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. He, J., and Hertweck, C. Iteration as programmed event during polyketide assembly; molecular analysis of the aureothin biosynthesis gene cluster. Chem. Biol. 10(12), 1225-1232 (2003).

    2. Shao, Z., and Zhao, H. DNA assembler: A synthetic biology tool for characterizing and engineering natural product gene clusters. Methods Enzymol. 517, 203-224 (2012).

    3. Friedrich, T., Van Heek, P., Lief, H., et al. Two binding sites of inhibitors in NADH: Ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose:ubiquinone oxidoreductase. Eur. J. Biochem. 219(1-2), 691-698 (1994).