belinostat   Click here for help

GtoPdb Ligand ID: 7496

Synonyms: Beleodaq® | PXD-101 | PXD101
Approved drug PDB Ligand
belinostat is an approved drug (FDA (2014))
Compound class: Synthetic organic
Comment: Belinostat is a pan-histone deacetylase (HDAC) inhibitor [1,3].
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: belinostat

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 4
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 103.88
Molecular weight 318.07
XLogP 1.95
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 ONC(=O)C=Cc1cccc(c1)S(=O)(=O)Nc1ccccc1
Isomeric SMILES ONC(=O)/C=C/c1cccc(c1)S(=O)(=O)Nc1ccccc1
InChI InChI=1S/C15H14N2O4S/c18-15(16-19)10-9-12-5-4-8-14(11-12)22(20,21)17-13-6-2-1-3-7-13/h1-11,17,19H,(H,16,18)/b10-9+
InChI Key NCNRHFGMJRPRSK-MDZDMXLPSA-N
References
1. Bradner JE, West N, Grachan ML, Greenberg EF, Haggarty SJ, Warnow T, Mazitschek R. (2010)
Chemical phylogenetics of histone deacetylases.
Nat Chem Biol, 6 (3): 238-243. [PMID:20139990]
2. Buckley MT, Yoon J, Yee H, Chiriboga L, Liebes L, Ara G, Qian X, Bajorin DF, Sun TT, Wu XR et al.. (2007)
The histone deacetylase inhibitor belinostat (PXD101) suppresses bladder cancer cell growth in vitro and in vivo.
J Transl Med, 5: 49. [PMID:17935615]
3. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, Qian X, Mills E, Berghs SC, Carey N et al.. (2008)
Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors.
Biochem J, 409 (2): 581-9. [PMID:17868033]
4. Plumb JA, Finn PW, Williams RJ, Bandara MJ, Romero MR, Watkins CJ, La Thangue NB, Brown R. (2003)
Pharmacodynamic response and inhibition of growth of human tumor xenografts by the novel histone deacetylase inhibitor PXD101.
Mol Cancer Ther, 2 (8): 721-8. [PMID:12939461]
5. Qian X, LaRochelle WJ, Ara G, Wu F, Petersen KD, Thougaard A, Sehested M, Lichenstein HS, Jeffers M. (2006)
Activity of PXD101, a histone deacetylase inhibitor, in preclinical ovarian cancer studies.
Mol Cancer Ther, 5 (8): 2086-95. [PMID:16928830]
6. Savickiene J, Treigyte G, Valiuliene G, Stirblyte I, Navakauskiene R. (2014)
Epigenetic and molecular mechanisms underlying the antileukemic activity of the histone deacetylase inhibitor belinostat in human acute promyelocytic leukemia cells.
Anticancer Drugs, 25 (8): 938-49. [PMID:24800886]