Clorobiocin

Clorobiocin is an aminocoumarin antibacterial that inhibits the enzyme DNA gyrase.[2][3]

Clorobiocin
Clinical data
Other namesChlorobiocin
ATC code
  • none
Identifiers
IUPAC name
  • (3S,4R,5R,6S)-6-[(8-chloro-4-hydroxy-3-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzene]amido}-2-oxo-2H-chromen-7-yl)oxy]-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl 5-methylpyrrole-2-carboxylate [1]
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC35H37ClN2O11
Molar mass697.13 g·mol−1
3D model (JSmol)
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(=O)C(=C(O4)O)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)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/h7-8,10-15,27,29-30,34,37,39,41,44H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1 N
  • Key:NOLDNICYUPLDOY-LFLQOBSNSA-N N
 NY (what is this?)  (verify)

References
  1. , http://www.drugbank.ca/drugs/DB03966.
  2. Pojer F, Wemakor E, Kammerer B, Chen H, Walsh CT, Li SM, Heide L (March 2003). "CloQ, a prenyltransferase involved in clorobiocin biosynthesis". Proceedings of the National Academy of Sciences of the United States of America. 100 (5): 2316–21. Bibcode:2003PNAS..100.2316P. doi:10.1073/pnas.0337708100. PMC 151338. PMID 12618544.
  3. Heide L (2009). "Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins". Biotechnology Advances. 27 (6): 1006–1014. doi:10.1016/j.biotechadv.2009.05.017. PMID 19463934.
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