tacedinaline   Click here for help

GtoPdb Ligand ID: 8367

Synonyms: CI-994 | CI994
Compound class: Synthetic organic
Comment: Tacedinaline inhibits the histone deacetylase enzyme HDAC1 [6], and is reported to have antitumour activity in preclinical studies [2,4-5].
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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

tacedinaline 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 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 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 84.22
Molecular weight 269.12
XLogP 1.43
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 CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
Isomeric SMILES CC(=O)Nc1ccc(cc1)C(=O)Nc1ccccc1N
InChI InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)
InChI Key VAZAPHZUAVEOMC-UHFFFAOYSA-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. Gediya LK, Belosay A, Khandelwal A, Purushottamachar P, Njar VC. (2008)
Improved synthesis of histone deacetylase inhibitors (HDIs) (MS-275 and CI-994) and inhibitory effects of HDIs alone or in combination with RAMBAs or retinoids on growth of human LNCaP prostate cancer cells and tumor xenografts.
Bioorg Med Chem, 16 (6): 3352-60. [PMID:18166465]
3. Liu L, Chen B, Qin S, Li S, He X, Qiu S, Zhao W, Zhao H. (2010)
A novel histone deacetylase inhibitor Chidamide induces apoptosis of human colon cancer cells.
Biochem Biophys Res Commun, 392 (2): 190-5. [PMID:20060381]
4. Loprevite M, Tiseo M, Grossi F, Scolaro T, Semino C, Pandolfi A, Favoni R, Ardizzoni A. (2005)
In vitro study of CI-994, a histone deacetylase inhibitor, in non-small cell lung cancer cell lines.
Oncol Res, 15 (1): 39-48. [PMID:15839304]
5. LoRusso PM, Demchik L, Foster B, Knight J, Bissery MC, Polin LM, Leopold 3rd WR, Corbett TH. (1996)
Preclinical antitumor activity of CI-994.
Invest New Drugs, 14 (4): 349-56. [PMID:9157069]
6. Methot JL, Chakravarty PK, Chenard M, Close J, Cruz JC, Dahlberg WK, Fleming J, Hamblett CL, Hamill JE, Harrington P et al.. (2008)
Exploration of the internal cavity of histone deacetylase (HDAC) with selective HDAC1/HDAC2 inhibitors (SHI-1:2).
Bioorg Med Chem Lett, 18 (3): 973-8. [PMID:18182289]