combretastatin A4   Click here for help

GtoPdb Ligand ID: 8854

Synonyms: CA-4 | combretastatin A-4 | NSC-613729
PDB Ligand
Compound class: Synthetic organic
Comment: Combretastatin A4 is the active metabolite of 8857. Combretastatin A4 interacts with the colchicine binding site of tubulin, which primarily resides within the β-tubulin subunit, at its interface with the α-subunit [3]. The compound has antineoplastic activity, inhibiting microtubule polymerization, and causing mitotic arrest and apoptosis, particularly targeting the tumour vasculature [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 57.15
Molecular weight 316.13
XLogP 3.64
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc(C=Cc2ccc(c(c2)O)OC)cc(c1OC)OC
Isomeric SMILES COc1cc(/C=C\c2ccc(c(c2)O)OC)cc(c1OC)OC
InChI InChI=1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
Bioactivity Comments
Inhibits colchicine binding to tubulin with an apparent Ki of 140nM [3].
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
tubulin beta 3 class III Hs Inhibitor Inhibition 8.2 pIC50 - 1
pIC50 8.2 (IC50 5.7x10-9 M) [1]
Description: Measuring cytotoxicity in cells expressing TUBB3 using the sulforhodamine B colorimetric assay.