AG14361   Click here for help

GtoPdb Ligand ID: 8094

Synonyms: AG 14361 | AG-14361
Compound class: Synthetic organic
Comment: AG14361 is a potent experimental inhibitor of poly (ADP-ribose) polymerase 1 (PARP1) [7]. Its discovery is described in [5], where it is compound 22.
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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 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 50.16
Molecular weight 320.16
XLogP 3.42
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 CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
Isomeric SMILES CN(Cc1ccc(cc1)c1nc2c3n1CCNC(=O)c3ccc2)C
InChI InChI=1S/C19H20N4O/c1-22(2)12-13-6-8-14(9-7-13)18-21-16-5-3-4-15-17(16)23(18)11-10-20-19(15)24/h3-9H,10-12H2,1-2H3,(H,20,24)
InChI Key SEKJSSBJKFLZIT-UHFFFAOYSA-N
No information available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
PARP is involved in repairing single-strand DNA breaks (nicks). In cells with mutations in other DNA repair enzymes such as the BRCA and PALB2 (Q86YC2) mutations in breast, ovarian and prostate cancers [1], PARP becomes more important for the DNA repair process. In such malignant cells, inhibition of PARP may therefore result in cell death due to accumulated DNA damage. Some PARP inhibitors cause irreversible binding of the enzyme to the DNA in addition to catalytic inhibition [4]. This may result in accumulation of toxic PARP-DNA complexes.