An inhibitor of DNA gyrase
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Novobiocin (sodium salt)

Item No. 18457

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[7-[[3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-α-L-lyxo-hexopyranosyl]oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-benzamide, monosodium salt
CAS Number
1476-53-5
Synonyms
  • NSC 2382
Molecular Formula
C31H35N2O11 • Na
Formula Weight
634.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 100 mg/ml
λmax
212, 249, 307 nm
SMILES
O[C@H]1[C@H](OC2=CC=C(C(O)=C(NC(C3=CC(C/C=C(C)\C)=C([O-])C=C3)=O)C(O4)=O)C4=C2C)OC(C)(C)[C@H](OC)[C@H]1OC(N)=O.[Na+]
InChi Code
InChI=1S/C31H36N2O11.Na/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29;/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37);/q;+1/p-1/t23-,25+,26-,29-;/m1./
InChi Key
WWPRGAYLRGSOSU-RNROJPEYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Novobiocin is a coumarin antibiotic, first isolated from Streptomyces species, that inhibits the ATPase activity of DNA gyrase.1 Its antibacterial activity arises from competitive inhibition of the ATPase reaction catalyzed by the GyrB subunit.1 In addition to permitting relaxation of negative supercoils, novobiocin has been used to generate positively supercoiled DNA.2 It also inhibits the chaperone activity of Hsp90 (IC50 = 700 mM).3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Collin, F., Karkare, S., and Maxwell, A. Exploiting bacterial DNA gyrase as a drug target: Current state and perspectives. Appl. Microbiol. Biotechnol. 92(3), 479-497 (2011).

    2. Lockshon, D., and Morris, D.R. Positively supercoiled plasmid DNA is produced by treatment of Escherichia coli with DNA gyrase inhibitors. Nucleic Acids Res. 11(10), 2999-3017 (1983).

    3. Allan, R.K., Mok, D., Ward, B.K., et al. Modulation of chaperone function and cochaperone interaction by novobiocin in the C-terminal domain of Hsp90: Evidence that coumarin antibiotics disrupt Hsp90 dimerization. The Journal of Biological Chemisty 281(11), 7161-7171 (2006).

    4. Hall, J.A., Seedarala, S., Zhao, H., et al. Novobiocin Analogues That Inhibit the MAPK Pathway. J. Med. Chem. 59(3), 925-933 (2016).