bradanicline   Click here for help

GtoPdb Ligand ID: 3969

Synonyms: ATA-101 | ATA101 | compound 7a [PMID 23126648] [4] | TC-5619 | TC5619
Compound class: Synthetic organic
Comment: Bradanicline is an investigational agonist of neuronal α7 subunit-containing nicotinic acetylcholine receptors [4].

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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 1
Rotatable bonds 5
Topological polar surface area 58.37
Molecular weight 361.18
XLogP 2.55
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 O=C(c1cc2c(o1)cccc2)NC1C2CCN(C1Cc1cccnc1)CC2
Isomeric SMILES O=C(c1cc2c(o1)cccc2)N[C@@H]1C2CCN([C@H]1Cc1cccnc1)CC2
InChI InChI=1S/C22H23N3O2/c26-22(20-13-17-5-1-2-6-19(17)27-20)24-21-16-7-10-25(11-8-16)18(21)12-15-4-3-9-23-14-15/h1-6,9,13-14,16,18,21H,7-8,10-12H2,(H,24,26)/t18-,21+/m0/s1
InChI Key OXKRFEWMSWPKKV-GHTZIAJQSA-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. Canning BJ, Liu Q, Tao M, DeVita R, Perelman M, Hay DW, Dicpinigaitis PV, Liang J. (2022)
Evidence for Alpha7 Nicotinic Receptor Activation During the Cough Suppressing Effects Induced by Nicotine and Identification of ATA-101 as a Potential Novel Therapy for the Treatment of Chronic Cough.
J Pharmacol Exp Ther, 380 (2): 94-103. [PMID:34782407]
2. Hauser TA, Kucinski A, Jordan KG, Gatto GJ, Wersinger SR, Hesse RA, Stachowiak EK, Stachowiak MK, Papke RL, Lippiello PM et al.. (2009)
TC-5619: an alpha7 neuronal nicotinic receptor-selective agonist that demonstrates efficacy in animal models of the positive and negative symptoms and cognitive dysfunction of schizophrenia.
Biochem Pharmacol, 78 (7): 803-12. [PMID:19482012]
3. Lieberman JA, Dunbar G, Segreti AC, Girgis RR, Seoane F, Beaver JS, Duan N, Hosford DA. (2013)
A randomized exploratory trial of an α-7 nicotinic receptor agonist (TC-5619) for cognitive enhancement in schizophrenia.
Neuropsychopharmacology, 38 (6): 968-75. [PMID:23303043]
4. Mazurov AA, Kombo DC, Hauser TA, Miao L, Dull G, Genus JF, Fedorov NB, Benson L, Sidach S, Xiao Y et al.. (2012)
Discovery of (2S,3R)-N-[2-(pyridin-3-ylmethyl)-1-azabicyclo[2.2.2]oct-3-yl]benzo[b]furan-2-carboxamide (TC-5619), a selective α7 nicotinic acetylcholine receptor agonist, for the treatment of cognitive disorders.
J Med Chem, 55 (22): 9793-809. [PMID:23126648]