Compound ID | 1833

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Novobiocin

Class: Aminocoumarin

Spectrum of activity: Gram-positive
Details of activity: Inhibits bacterial DNA gyrase via binding to the ATP-binding site of the GyrB subunit of the enzyme. Novobiocin acts as competitive inhibitor of the ATPase reaction; active mainly against Gram-positive bacteria.
Propensity to select resistant mutants: Yes
Description: Streptomyces natural product
Year first mentioned: 1955
Highest development stage: Approved by FDA in 1964
Development status: Discontinued
Reason dropped: Terminated due to toxicity
Chemical structure(s):
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Molecular weight: 612.63
Iso. SMILES: CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)O[C@H]4[C@@H]([C@@H]([C@H](C(O4)(C)C)OC)OC(=O)N)O
InChI Key: YJQPYGGHQPGBLI-KGSXXDOSSA-N
Can. SMILES: CC(=CCC1=CC(=CC=C1O)C(=O)NC2=C(C3=C(C(=C(C=C3)O[C@H]4[C@@H]([C@@H]([C@H](C(C)(C)O4)OC)OC(=O)N)O)C)OC2=O)O)C
InChI: InChI=1S/C31H36N2O11/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)/t23-,25+,26-,29-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54675769
Guide to Pharmacology: novobiocin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/2591171/
  • https://pubmed.ncbi.nlm.nih.gov/28019639/
  • https://pubmed.ncbi.nlm.nih.gov/29746111/
  • https://pubmed.ncbi.nlm.nih.gov/13273516/

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