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 developmental phase:	Approved by FDA in 1964
Development status:	Discontinued
Reason Dropped:	Terminated due to toxicity

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	YJQPYGGHQPGBLI-KGSXXDOSSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54675769

External links:
Guide to Pharmacology:	novobiocin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/13273516/
Citations:	https://pubmed.ncbi.nlm.nih.gov/2591171/ https://pubmed.ncbi.nlm.nih.gov/28019639/ https://pubmed.ncbi.nlm.nih.gov/29746111/