Compound ID | 1834

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Chlorobiocin (NSC 227186 in NCI compound library)

Class: Aminocoumarin

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: DNA synthesis inhibitor. Inhibits bacterial DNA gyrase via binding to the ATP-binding site of the GyrB subunit of the enzyme; acts as competitive inhibitor of the ATPase reaction similar to novobiocin
Target Pathogen: Active against staphylococci and weak activity against Escherichia coli
Propensity to select resistant mutants: Yes
Description: Streptomyces natural product
Year first mentioned: 1972
Development status: Experimental
Chemical structure(s):
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Molecular weight: 697.13
Iso. 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 Key: FJAQNRBDVKIIKK-LFLQOBSNSA-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)C5=CC=C(C)N5)O)Cl)OC2=O)O)C
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/54706138
Guide to Pharmacology: clorobiocin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/12480894/
  • https://pubmed.ncbi.nlm.nih.gov/12670542/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC375324/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183811/?page=8

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