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
1. Bisacchi GS, Manchester JI. (2015)
A New-Class Antibacterial-Almost. Lessons in Drug Discovery and Development: A Critical Analysis of More than 50 Years of Effort toward ATPase Inhibitors of DNA Gyrase and Topoisomerase IV.
ACS Infect Dis, 1 (1): 4-41. [PMID:27620144]
2. Hooper DC, Wolfson JS, McHugh GL, Winters MB, Swartz MN. (1982)
Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth.
Antimicrob Agents Chemother, 22 (4): 662-71. [PMID:6295263]
3. Maxwell A. (1999)
DNA gyrase as a drug target.
Biochem Soc Trans, 27 (2): 48-53. [PMID:10093705]