compound 19 [PMID: 7707314]   Click here for help

GtoPdb Ligand ID: 8892

Compound class: Synthetic organic
Comment: Compound 19 is reported as an inhibitor of topoisomerase I [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 94.31
Molecular weight 441.03
XLogP 2.98
No. Lipinski's rules broken 0
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Canonical SMILES CCC1(O)C(=O)OCc2c1cc1c3nc4cnc(cc4c(c3Cn1c2=O)C)Br
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4cnc(cc4c(c3Cn1c2=O)C)Br
InChI InChI=1S/C20H16BrN3O4/c1-3-20(27)13-5-15-17-11(7-24(15)18(25)12(13)8-28-19(20)26)9(2)10-4-16(21)22-6-14(10)23-17/h4-6,27H,3,7-8H2,1-2H3/t20-/m0/s1
Bioactivity Comments
Compound 19 is a highly potent cytotoxic agent in vitro and in vivo [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DNA topoisomerase I Bt Inhibitor Inhibition 7.6 pIC50 - 1
pIC50 7.6 (IC50 2.8x10-8 M) [1]
Description: Concentration of compound required to produce approximately 50% fragmentation of P-32 end- labeled DNA in the presence of calf thymus topoisomerase I.