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compound 14b [PMID: 25742366]   Click here for help

GtoPdb Ligand ID: 8684

Compound class: Synthetic organic
Comment: Compound 14b is reported as an irreversible and selective inhibitor of protein arginine deiminase type III (PADI3) [1].
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 6
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 90.62
Molecular weight 436.14
XLogP 3.98
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 ClCC(NCCCC1NC(=O)N(C1O)Cc1cccc(c1)c1ccccc1Cl)N
Isomeric SMILES ClCC(NCCCC1NC(=O)N(C1O)Cc1cccc(c1)c1ccccc1Cl)N
InChI InChI=1S/C21H26Cl2N4O2/c22-12-19(24)25-10-4-9-18-20(28)27(21(29)26-18)13-14-5-3-6-15(11-14)16-7-1-2-8-17(16)23/h1-3,5-8,11,18-20,25,28H,4,9-10,12-13,24H2,(H,26,29)
InChI Key TXEBWPPWSVMYOA-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/)
Bioactivity Comments
As compound 14b is an irreversible inhibitor the authors provide inhibition values as rate constants (kinact/KI) as a measure of inhibitory activity. NB click on the down arrow at the end of the row in the table below to reveal the rate constant.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
peptidyl arginine deiminase 4 Hs Inhibitor Irreversible inhibition - - - 1
⤷ [1]
Description: Kinact/KI = 1.46x103 M-1 min-1
peptidyl arginine deiminase 3 Primary target of this compound Hs Inhibitor Irreversible inhibition - - - 1
⤷ [1]
Description: Kinact/KI = 1.56x104 M-1 min-1