Chlorobiocin (NSC 227186 in NCI compound library)

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. Clorobiocin acts as competitive inhibitor of the ATPase reaction, very similar to novobiocin; active against staphylococci and little activity against E. coli
Propensity to select resistant mutants:	Yes
Description:	Streptomyces natural product
Year first mentioned:	1972
Development status:	Experimental

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)C5=CC=C(C)N5)O)Cl)OC2=O)O)C
Isomeric SMILES:	CC1=CC=C(N1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)O)Cl)O
InChI:	InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
InChI Key:	FJAQNRBDVKIIKK-LFLQOBSNSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/54706138

External links:
Guide to Pharmacology:	clorobiocin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183811/?page=8
Citations:	https://pubmed.ncbi.nlm.nih.gov/12480894/ https://pubmed.ncbi.nlm.nih.gov/12670542/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC375324/