compound 5z [PMID: 8410981]   Click here for help

GtoPdb Ligand ID: 8893

Synonyms: 10,11-Methylenedioxy-20S-camptothecin
Compound class: Synthetic organic
Comment: Compound 5z is an analogue of the natural alkaloid camptothecin (PubChem CID 24360) [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 99.88
Molecular weight 392.1
XLogP 2.4
No. Lipinski's rules broken 0
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Canonical SMILES CCC1(O)C(=O)OCc2c1cc1c3nc4cc5OCOc5cc4cc3Cn1c2=O
Isomeric SMILES CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4cc5OCOc5cc4cc3Cn1c2=O
InChI InChI=1S/C21H16N2O6/c1-2-21(26)13-5-15-18-11(7-23(15)19(24)12(13)8-27-20(21)25)3-10-4-16-17(29-9-28-16)6-14(10)22-18/h3-6,26H,2,7-9H2,1H3/t21-/m0/s1
Bioactivity Comments
Compound 5z is cytotoxic 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 2.7x10-8 M) [1]
Description: Inhibition of pBR322 DNA cleavage by calf thymus DNA topoisomerase I.