clorobiocin   Click here for help

GtoPdb Ligand ID: 12127

Synonyms: chlorobiocin | RP 18,631
PDB Ligand
Comment: Clorobiocin was originally isolated from the actinomycete Streptomyces roseochromogenes and belongs to the aminocoumarins.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 189.78
Molecular weight 696.21
XLogP 6.53
No. Lipinski's rules broken 1
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Canonical SMILES CO[C@@H]1[C@@H](OC(=O)c2ccc([nH]2)C)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1Cl)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)O
Isomeric SMILES Cc1ccc([nH]1)C(=O)O[C@H]1[C@H]([C@@H](OC([C@@H]1OC)(C)C)Oc1c(c2c(cc1)c(c(c(=O)o2)NC(=O)c1cc(c(cc1)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
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Mechanism Of Action and Pharmacodynamic Effects Click here for help
Clorobiocin is a potent inhibitor of DNA gyrase, a type II DNA topoisomerase that catalyzes the negative supercoiling of DNA and is essential in all bacteria but absent from higher eukaryotes [2-3].