volasertib   Click here for help

GtoPdb Ligand ID: 7947

Synonyms: BI 6727 | BI-6727
PDB Ligand
Compound class: Synthetic organic
Comment: Volasertib is an ATP-competitive, investigational inhibitor of polo-like kinase 1 (PLK1). It is the second in a novel class of drugs called dihydropteridinone derivatives [3]. This compound is represented on PubChem by CID 10461508. This CID varies slightly in its chiral specification from our ligand entry. Our structure was drawn from the image submitted to the WHO for the INN (note that the long chemical name provided for the INN registration is not sufficient to resolve absolute stereochemistry as depicted in the accompanying image). Some bioactivity may be linked to the trihydrochloride salt form.
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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
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 CDK toolkit. 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 10
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 106.17
Molecular weight 618.4
XLogP 4.2
No. Lipinski's rules broken 0
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.

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Canonical SMILES CCC1N(C(C)C)c2nc(ncc2N(C1=O)C)Nc1ccc(cc1OC)C(=O)NC1CCC(CC1)N1CCN(CC1)CC1CC1
Isomeric SMILES CC[C@H]1N(C(C)C)c2nc(ncc2N(C1=O)C)Nc1ccc(cc1OC)C(=O)N[C@@H]1CC[C@H](CC1)N1CCN(CC1)CC1CC1
InChI InChI=1S/C34H50N8O3/c1-6-28-33(44)39(4)29-20-35-34(38-31(29)42(28)22(2)3)37-27-14-9-24(19-30(27)45-5)32(43)36-25-10-12-26(13-11-25)41-17-15-40(16-18-41)21-23-7-8-23/h9,14,19-20,22-23,25-26,28H,6-8,10-13,15-18,21H2,1-5H3,(H,36,43)(H,35,37,38)/t25-,26-,28-/m1/s1
InChI Key SXNJFOWDRLKDSF-STROYTFGSA-N
References
1. Barr FA, Silljé HH, Nigg EA. (2004)
Polo-like kinases and the orchestration of cell division.
Nat Rev Mol Cell Biol, 5 (6): 429-40. [PMID:15173822]
2. Santamaria A, Neef R, Eberspächer U, Eis K, Husemann M, Mumberg D, Prechtl S, Schulze V, Siemeister G, Wortmann L et al.. (2007)
Use of the novel Plk1 inhibitor ZK-thiazolidinone to elucidate functions of Plk1 in early and late stages of mitosis.
Mol Biol Cell, 18 (10): 4024-36. [PMID:17671160]
3. Schöffski P. (2009)
Polo-like kinase (PLK) inhibitors in preclinical and early clinical development in oncology.
Oncologist, 14 (6): 559-70. [PMID:19474163]
4. Zhang Q, Xia Z, Mitten MJ, Lasko LM, Klinghofer V, Bouska J, Johnson EF, Penning TD, Luo Y, Giranda VL et al.. (2012)
Hit to Lead optimization of a novel class of squarate-containing polo-like kinases inhibitors.
Bioorg Med Chem Lett, 22 (24): 7615-22. [PMID:23103095]