SB-415286   Click here for help

GtoPdb Ligand ID: 8019

Synonyms: SB 415286 | SB415286
Compound class: Synthetic organic
Comment: SB-415286 is a potent glycogen synthase kinase-3 (GSK-3) inhibitor which is equipotent at the α and β isozymes [2].
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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

SB-415286 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 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 3
Rotatable bonds 4
Topological polar surface area 121.57
Molecular weight 359.03
XLogP 3.26
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 O=C1NC(=O)C(=C1Nc1ccc(c(c1)Cl)O)c1ccccc1[N+](=O)[O-]
Isomeric SMILES O=C1NC(=O)C(=C1Nc1ccc(c(c1)Cl)O)c1ccccc1[N+](=O)[O-]
InChI InChI=1S/C16H10ClN3O5/c17-10-7-8(5-6-12(10)21)18-14-13(15(22)19-16(14)23)9-3-1-2-4-11(9)20(24)25/h1-7,21H,(H2,18,19,22,23)
InChI Key PQCXVIPXISBFPN-UHFFFAOYSA-N
References
1. Cai Z, Zhao Y, Zhao B. (2012)
Roles of glycogen synthase kinase 3 in Alzheimer's disease.
Curr Alzheimer Res, 9 (7): 864-79. [PMID:22272620]
2. Coghlan MP, Culbert AA, Cross DA, Corcoran SL, Yates JW, Pearce NJ, Rausch OL, Murphy GJ, Carter PS, Roxbee Cox L et al.. (2000)
Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription.
Chem Biol, 7 (10): 793-803. [PMID:11033082]
3. Eldar-Finkelman H, Schreyer SA, Shinohara MM, LeBoeuf RC, Krebs EG. (1999)
Increased glycogen synthase kinase-3 activity in diabetes- and obesity-prone C57BL/6J mice.
Diabetes, 48 (8): 1662-6. [PMID:10426388]
4. Hurtado DE, Molina-Porcel L, Carroll JC, Macdonald C, Aboagye AK, Trojanowski JQ, Lee VM. (2012)
Selectively silencing GSK-3 isoforms reduces plaques and tangles in mouse models of Alzheimer's disease.
J Neurosci, 32 (21): 7392-402. [PMID:22623685]
5. Nikoulina SE, Ciaraldi TP, Mudaliar S, Mohideen P, Carter L, Henry RR. (2000)
Potential role of glycogen synthase kinase-3 in skeletal muscle insulin resistance of type 2 diabetes.
Diabetes, 49 (2): 263-71. [PMID:10868943]
6. Takashima A, Noguchi K, Sato K, Hoshino T, Imahori K. (1993)
Tau protein kinase I is essential for amyloid beta-protein-induced neurotoxicity.
Proc Natl Acad Sci USA, 90 (16): 7789-93. [PMID:8356085]