combretastatin A4   

GtoPdb Ligand ID: 8854

Synonyms: CA-4 | combretastatin A-4 | NSC-613729
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].
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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-
InChI Key HVXBOLULGPECHP-WAYWQWQTSA-N
Classification
Compound class Synthetic organic
Prodrug fosbretabulin
IUPAC Name
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
Synonyms
CA-4 | combretastatin A-4 | NSC-613729
Database Links
CAS Registry No. 117048-59-6
ChEMBL Ligand CHEMBL67
GtoPdb PubChem SID 252827511
PubChem CID 5351344
RCSB PDB Ligand 7BA
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Tocris
Combretastatin A4
Cat. No. 1495