LAU463   Click here for help

GtoPdb Ligand ID: 12405

Synonyms: compound 8n [PMID: 29481759]
Compound class: Synthetic organic
Comment: LAU463 is an allosteric modulator of GABAA receptors [1,4].
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 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 53.93
Molecular weight 370.2
XLogP 2.57
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 COC1=CC=C(C=C1)N2C(=O)C3=CNC4=CC(=CC=C4C3=N2)Br
Isomeric SMILES COC1=CC=C(C=C1)N2N=C3C(=CNC4=C3C=CC(Br)=C4)C2=O
InChI InChI=1S/C17H12BrN3O2/c1-23-12-5-3-11(4-6-12)21-17(22)14-9-19-15-8-10(18)2-7-13(15)16(14)20-21/h2-9,19H,1H3
InChI Key CAJJWNTVLDPILI-UHFFFAOYSA-N
References
1. Knutson DE, Kodali R, Divović B, Treven M, Stephen MR, Zahn NM, Dobričić V, Huber AT, Meirelles MA, Verma RS et al.. (2018)
Design and Synthesis of Novel Deuterated Ligands Functionally Selective for the γ-Aminobutyric Acid Type A Receptor (GABAAR) α6 Subtype with Improved Metabolic Stability and Enhanced Bioavailability.
J Med Chem, 61 (6): 2422-2446. [PMID:29481759]
2. Sieghart W, Chiou LC, Ernst M, Fabjan J, M Savic; M, Lee MT. (2022)
α 6-Containing GABAA Receptors: Functional Roles and Therapeutic Potentials.
Pharmacol Rev, 74 (1): 238-270. [PMID:35017178]
3. Sieghart W, Savić MM. (2018)
International Union of Basic and Clinical Pharmacology. CVI: GABAA Receptor Subtype- and Function-selective Ligands: Key Issues in Translation to Humans.
Pharmacol Rev, 70 (4): 836-878. [PMID:30275042]
4. Varagic Z, Wimmer L, Schnürch M, Mihovilovic MD, Huang S, Rallapalli S, Cook JM, Mirheydari P, Ecker GF, Sieghart W et al.. (2013)
Identification of novel positive allosteric modulators and null modulators at the GABAA receptor α+β- interface.
Br J Pharmacol, 169 (2): 371-83. [PMID:23472852]