AMG28   Click here for help

GtoPdb Ligand ID: 12186

Synonyms: example 240 [WO2009158011A1] | inhibitor 3 [PMID: 33944571]
PDB Ligand
Compound class: Synthetic organic
Comment: AMG28 is a small molecule multi-kinase inhibitor, with activity against NF-κB inducing kinase (NIK; MAP3K14), Tau tubulin kinase 1 (TTBK1), and the lipid modifying phosphoinositide kinase, FYVE-type zinc finger containing (PIKFYVE), amongst others [3]. It is one of the kinase inhibitors claimed in Amgen patent WO2009158011A1 [1].
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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 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 4
Hydrogen bond donors 3
Rotatable bonds 0
Topological polar surface area 87.82
Molecular weight 332.16
XLogP 2.81
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 Nc1ncc2c(n1)c1c(CCC2)[nH]c2c1cc(C#CC(O)(C)C)cc2
Isomeric SMILES CC(C)(C#Cc1cc2c(cc1)[nH]c1c2c2c(CCC1)cnc(n2)N)O
InChI InChI=1S/C20H20N4O/c1-20(2,25)9-8-12-6-7-15-14(10-12)17-16(23-15)5-3-4-13-11-22-19(21)24-18(13)17/h6-7,10-11,23,25H,3-5H2,1-2H3,(H2,21,22,24)
InChI Key DGLFSNZWRYADFC-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/)
References
1. Chen G, Cushing TD, Fisher B, He X, Li K, Li Z, Mcgee L, Pattaropong V, Faulder P, Seganish JL et al.. (2009)
Alkynyl alcohols as kinase inhibitors.
Patent number: WO2009158011A1. Assignee: Amgen Inc.. Priority date: 26/06/2008. Publication date: 30/12/2009.
2. Drewry DH, Potjewyd FM, Bayati A, Smith JL, Dickmander RJ, Howell S, Taft-Benz S, Min SM, Hossain MA, Heise M et al.. (2022)
Identification and Utilization of a Chemical Probe to Interrogate the Roles of PIKfyve in the Lifecycle of β-Coronaviruses.
J Med Chem, 65 (19): 12860-12882. [PMID:36111834]
3. Halkina T, Henderson JL, Lin EY, Himmelbauer MK, Jones JH, Nevalainen M, Feng J, King K, Rooney M, Johnson JL et al.. (2021)
Discovery of Potent and Brain-Penetrant Tau Tubulin Kinase 1 (TTBK1) Inhibitors that Lower Tau Phosphorylation In Vivo.
J Med Chem, 64 (9): 6358-6380. [PMID:33944571]