BMS-833923   Click here for help

GtoPdb Ligand ID: 8202

Synonyms: BMS 833923 | BMS833923 | XL 139 | XL-139 | XL139
Compound class: Synthetic organic
Comment: BMS-833923 is a high affinity antagonist of the class frizzled GPCR, smoothened (SMO) [1,3]. BMS-833923 is compound 163 in patent US8222263 [2].
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 3
Rotatable bonds 8
Topological polar surface area 78.94
Molecular weight 473.22
XLogP 5.76
No. Lipinski's rules broken 1
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 CNCc1ccc(c(c1)NC(=O)c1ccc(cc1)Nc1nc2ccccc2c(n1)c1ccccc1)C
Isomeric SMILES CNCc1ccc(c(c1)NC(=O)c1ccc(cc1)Nc1nc2ccccc2c(n1)c1ccccc1)C
InChI InChI=1S/C30H27N5O/c1-20-12-13-21(19-31-2)18-27(20)33-29(36)23-14-16-24(17-15-23)32-30-34-26-11-7-6-10-25(26)28(35-30)22-8-4-3-5-9-22/h3-18,31H,19H2,1-2H3,(H,33,36)(H,32,34,35)
InChI Key KLRRGBHZCJLIEL-UHFFFAOYSA-N
References
1. Akare UR, Bandaru S, Shaheen U, Singh PK, Tiwari G, Singare P, Nayarisseri A, Banerjee T. (2014)
Molecular docking approaches in identification of High affinity inhibitors of Human SMO receptor.
Bioinformation, 10 (12): 737-42. [PMID:25670876]
2. Bahceci S, Bajjalieh W, Chen J, Epshteyn S, Forsyth TP, Huynh TP, Kim BG, Leahy JW, Lee MS, Lewis GL et al.. (2012)
Inhibitors of hedgehog pathway.
Patent number: US8222263. Assignee: Exelixis Patent Company Llc. Priority date: 14/03/2007. Publication date: 17/07/2012.
3. Sandhiya S, Melvin G, Kumar SS, Dkhar SA. (2013)
The dawn of hedgehog inhibitors: Vismodegib.
J Pharmacol Pharmacother, 4 (1): 4-7. [PMID:23662017]