TH5487   Click here for help

GtoPdb Ligand ID: 10184

Synonyms: TH-5487
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: TH5487 is a selective, active-site inhibitor of 8-oxoguanine DNA glycosylase (OGG1) [2]. OGG1 repairs 8-hydroxy-2′-deoxyguanosine (8-oxoG) DNA defects that can be induced by reactive oxygen species (ROS) at sites of inflammation. TH5487 inhibits OGG1-mediated proinflammatory activity in allergic states. In a mouse model of allergic airway inflammation TH5487 reduced NF-κB-mediated expression of proinflammatory cytokines/chemokines and inhibited immune cell recruitment into the lungs with an associated reduction in goblet cell hyperplasia and mucus production [1].

TH5487 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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 70.13
Molecular weight 539.97
XLogP 3.86
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES Ic1ccc(cc1)NC(=O)N1CCC(CC1)n1c(=O)[nH]c2c1cccc2Br
Isomeric SMILES Ic1ccc(cc1)NC(=O)N1CCC(CC1)n1c(=O)[nH]c2c1cccc2Br
InChI InChI=1S/C19H18BrIN4O2/c20-15-2-1-3-16-17(15)23-19(27)25(16)14-8-10-24(11-9-14)18(26)22-13-6-4-12(21)5-7-13/h1-7,14H,8-11H2,(H,22,26)(H,23,27)
InChI Key FZLKVWWPFOLPKF-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel