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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 fosbretabulin. 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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

combretastatin A4 is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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-
InChI Key HVXBOLULGPECHP-WAYWQWQTSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Prodrug fosbretabulin
IUPAC Name Click here for help
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
Synonyms Click here for help
CA-4 | combretastatin A-4 | NSC-613729
Database Links Click here for help
CAS Registry No. 117048-59-6
ChEMBL Ligand CHEMBL67
GtoPdb PubChem SID 252827511
PubChem CID 5351344
RCSB PDB Ligand 7BA
Search Google for chemical match using the InChIKey HVXBOLULGPECHP-WAYWQWQTSA-N
Search Google for chemicals with the same backbone HVXBOLULGPECHP
UniChem Compound Search for chemical match using the InChIKey HVXBOLULGPECHP-WAYWQWQTSA-N
UniChem Connectivity Search for chemical match using the InChIKey HVXBOLULGPECHP-WAYWQWQTSA-N

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MedChemExpress
Combretastatin A4 (links to external site)
Cat. No. HY-N2146
(Same CID)