dichloroacetate   Click here for help

GtoPdb Ligand ID: 4518

Abbreviated name: DCA
Synonyms: dichloroacetic acid
Compound class: Synthetic organic
Comment: Dichloroacetate (DCA) is an orally available small molecule pyruvate dehydrogenase kinase inhibitor [4]. It acts as a metabolic regulator and has anti-cancer potential by promoting glucose oxidation over glycolysis, glycolysis being the metabolic pathway (Warburg effect) utilised by most cancer cells to resist apoptosis and gain proliferative advantage [1-3].
ChEMBL represents this compound without the charge (see link above).
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 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 40.13
Molecular weight 126.94
XLogP 0.09
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 ClC(C(=O)[O-])Cl
Isomeric SMILES ClC(C(=O)[O-])Cl
InChI InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)/p-1
InChI Key JXTHNDFMNIQAHM-UHFFFAOYSA-M
References
1. James MO, Jahn SC, Zhong G, Smeltz MG, Hu Z, Stacpoole PW. (2017)
Therapeutic applications of dichloroacetate and the role of glutathione transferase zeta-1.
Pharmacol Ther, 170: 166-180. [PMID:27771434]
2. Kankotia S, Stacpoole PW. (2014)
Dichloroacetate and cancer: new home for an orphan drug?.
Biochim Biophys Acta, 1846 (2): 617-29. [PMID:25157892]
3. Michelakis ED, Webster L, Mackey JR. (2008)
Dichloroacetate (DCA) as a potential metabolic-targeting therapy for cancer.
Br J Cancer, 99 (7): 989-94. [PMID:18766181]
4. Sutendra G, Michelakis ED. (2013)
Pyruvate dehydrogenase kinase as a novel therapeutic target in oncology.
Front Oncol, 3: 38. [PMID:23471124]