Compound ID | 1836

Update compound information

Isovanillobiocin

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. Less active than clorobiocin
Propensity to select resistant mutants: Yes
Description: Streptomyces natural product; clorobiocin analog
Year first mentioned: 2004
Development status: Experimental
Chemical structure(s):
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Molecular weight: 659.04
Iso. SMILES: CC1=CC=C(N1)C(=O)OC2C(C(C(OC2OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)OC)O)Cl)(C)C)OC)O
InChI Key: AKYRQFMQZJFLAE-UHFFFAOYSA-N
Can. SMILES: CC1=CC=C(C(=O)OC2C(C(C(C)(C)OC2OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CC=C(C(=C5)OC)O)O)Cl)OC)O)N1
InChI: InChI=1S/C31H31ClN2O12/c1-13-6-9-16(33-13)28(39)45-25-23(37)26(42-5)31(2,3)46-30(25)43-18-11-8-15-22(36)21(29(40)44-24(15)20(18)32)34-27(38)14-7-10-17(35)19(12-14)41-4/h6-12,23,25-26,30,33,35-37H,1-5H3,(H,34,38)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/76181969
Guide to Pharmacology: isovanillobiocin
Citation: https://www.jstage.jst.go.jp/article/antibiotics1968/57/3/57_3_205/_article

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