WAY-316606   Click here for help

GtoPdb Ligand ID: 9945

Synonyms: compound 1 [PMID: 19072540]
Compound class: Synthetic organic
Comment: WAY-316606 was originally identified as a small molecule inhibitor of the endogenous Wnt antagonist sFRP-1 (a.k.a. SARP2), as a novel anabolic agent for the treatment of osteoporosis or other bone-related disorders [3]. Mechanistically it binds to sFRP-1 and out-competes Wnt binding to sFRP-1, thereby releasing Wnt for binding to the LRP-frizzled receptor complex, an effect that ultimately promotes canonical Wnt signaling and increases anabolic bone formation [1]. Subsequent study has found that WAY-316606 may have potential as a hair re-growth strategy with potential clinical relevance for treatment of human hair loss disorders [2]. WAY-316606 was found to enhance hair shaft production, hair shaft keratin expression, and reduce spontaneous hair follicle regression in ex vivo human scalp explants, via a canonical Wnt/β-catenin-dependent mechanism.
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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 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 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 109.1
Molecular weight 448.07
XLogP 2.93
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=S(=O)(c1cc(ccc1C(F)(F)F)S(=O)(=O)c1ccccc1)NC1CCNCC1
Isomeric SMILES O=S(=O)(c1cc(ccc1C(F)(F)F)S(=O)(=O)c1ccccc1)NC1CCNCC1
InChI InChI=1S/C18H19F3N2O4S2/c19-18(20,21)16-7-6-15(28(24,25)14-4-2-1-3-5-14)12-17(16)29(26,27)23-13-8-10-22-11-9-13/h1-7,12-13,22-23H,8-11H2
InChI Key ITBGJNVZJBVPLJ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-(benzenesulfonyl)-N-piperidin-4-yl-2-(trifluoromethyl)benzenesulfonamide
Synonyms Click here for help
compound 1 [PMID: 19072540]
Database Links Click here for help
BindingDB Ligand 50265467
CAS Registry No. 915759-45-4 (source: PubChem)
ChEMBL Ligand CHEMBL495575
GtoPdb PubChem SID 374883832
PubChem CID 16727102
Search Google for chemical match using the InChIKey ITBGJNVZJBVPLJ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ITBGJNVZJBVPLJ
UniChem Compound Search for chemical match using the InChIKey ITBGJNVZJBVPLJ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ITBGJNVZJBVPLJ-UHFFFAOYSA-N