GSK484   Click here for help

GtoPdb Ligand ID: 8577

Synonyms: GSK 484 | GSK-484
Compound class: Synthetic organic
Comment: GSK484 binds to peptidyl arginine deiminase, type IV (PADI4; Q9UM07) and inhibits its activity [1]. PADI4 contributes to regulating the histone code by effecting the citrullination/deimination of histones. PADI4 has strong associations with cancer and immune and inflammatory processes. GSK484 will be a useful tool to enhance understanding of the normal and pathological functions of PADI4.
This is a compound from the Structural Genomics Consortium's (SGC) Epigenetics Probes Collection, developed in collaboration with GlaxoSmithKline (GSK).
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 2
Rotatable bonds 6
Topological polar surface area 98.54
Molecular weight 473.24
XLogP 3.41
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 COc1cc(cc2c1n(C)c(n2)c1cc2c(n1CC1CC1)cccc2)C(=O)N1CCC(C(C1)N)O
Isomeric SMILES COc1cc(cc2c1n(C)c(n2)c1cc2c(n1CC1CC1)cccc2)C(=O)N1CC[C@H]([C@H](C1)N)O
InChI InChI=1S/C27H31N5O3/c1-30-25-20(11-18(13-24(25)35-2)27(34)31-10-9-23(33)19(28)15-31)29-26(30)22-12-17-5-3-4-6-21(17)32(22)14-16-7-8-16/h3-6,11-13,16,19,23,33H,7-10,14-15,28H2,1-2H3/t19-,23+/m0/s1
InChI Key BDYDINKSILYBOL-WMZHIEFXSA-N
References
1. Lewis HD, Liddle J, Coote JE, Atkinson SJ, Barker MD, Bax BD, Bicker KL, Bingham RP, Campbell M, Chen YH et al.. (2015)
Inhibition of PAD4 activity is sufficient to disrupt mouse and human NET formation.
Nat Chem Biol, 11 (3): 189-91. [PMID:25622091]