compound 36 [PMID: 34843241]   Click here for help

GtoPdb Ligand ID: 12713

Synonyms: example 48 [WO2012056478]
Compound class: Synthetic organic
Comment: This compound is reported as an inhibitor of calcium release-activated calcium (CRAC) channel activity [2]. CRAC channels contain Orai1 (the pore-forming subunit) and stromal interaction molecule 1 (STIM1, which senses Ca2+ levels in the endoplasmic reticulum), and they mediate influx of Ca2+ ions into T cells in response to antigen engagement. CRAC function inhibitors have anti-inflammatory potential via blocking NFAT-mediated T cell activation. The chemical structure was claimed in Lupin Limited's 2012 patent WO2012056478A1 [1].
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 1
Rotatable bonds 5
Topological polar surface area 71
Molecular weight 421.4
XLogP 2.97
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 CC1=C(C=CC=C1C2=NN(C)C(=O)O2)C3=CC=C(C=C3)NC(=O)C4=C(C=CC=C4F)F
Isomeric SMILES O=C1OC(=NN1C)C=2C=CC=C(C3=CC=C(NC(C4=C(F)C=CC=C4F)=O)C=C3)C2C
InChI InChI=1S/C23H17F2N3O3/c1-13-16(5-3-6-17(13)22-27-28(2)23(30)31-22)14-9-11-15(12-10-14)26-21(29)20-18(24)7-4-8-19(20)25/h3-12H,1-2H3,(H,26,29)
InChI Key ZKAHFFVNALZECX-UHFFFAOYSA-N
References
1. Irlapati NR, Deshmukh GK, Karche VP, Jachak SM, Sinha N, Palle VP, Kamboj RK. (2012)
Oxazole and isoxazole CRAC modulators.
Patent number: WO2012056478. Assignee: Lupin Limited. Priority date: 31/10/2011. Publication date: 03/05/2012.
2. Khedkar NR, Irlapatti NR, Dadke D, Kanoje V, Shaikh Z, Karche V, Shinde V, Deshmukh G, Patil A, Jachak S et al.. (2021)
Discovery of a Novel Potent and Selective Calcium Release-Activated Calcium Channel Inhibitor: 2,6-Difluoro-N-(2'-methyl-3'-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-[1,1'-biphenyl]-4-yl)benzamide. Structure-Activity Relationship and Preclinical Characterization.
J Med Chem, 64 (23): 17004-17030. [PMID:34843241]