benzoquinazolinone 12   Click here for help

GtoPdb Ligand ID: 8549

Synonyms: compound A [PMID: 26582730] | compound C [PMID: 29025977] [3] | T662
Compound class: Synthetic organic
Comment: This compound is a selective M1 muscarinic acetylcholine receptor positive allosteric modulator [3]. In vivo it induces cholinergic side effects such as salivation, diarrhea, and emesis [2].
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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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Click here for structure editor
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 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 85.83
Molecular weight 465.22
XLogP 4.48
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 OC1CCCCC1n1cnc2c(c1=O)cc(c1c2cccc1)Cc1ccc(nc1)c1cnn(c1)C
Isomeric SMILES O[C@H]1CCCC[C@@H]1n1cnc2c(c1=O)cc(c1c2cccc1)Cc1ccc(nc1)c1cnn(c1)C
InChI InChI=1S/C28H27N5O2/c1-32-16-20(15-31-32)24-11-10-18(14-29-24)12-19-13-23-27(22-7-3-2-6-21(19)22)30-17-33(28(23)35)25-8-4-5-9-26(25)34/h2-3,6-7,10-11,13-17,25-26,34H,4-5,8-9,12H2,1H3/t25-,26-/m0/s1
InChI Key SXJQBWJPNSOKQV-UIOOFZCWSA-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. Abdul-Ridha A, Lane JR, Mistry SN, López L, Sexton PM, Scammells PJ, Christopoulos A, Canals M. (2014)
Mechanistic insights into allosteric structure-function relationships at the M1 muscarinic acetylcholine receptor.
J Biol Chem, 289 (48): 33701-11. [PMID:25326383]
2. Alt A, Pendri A, Bertekap Jr RL, Li G, Benitex Y, Nophsker M, Rockwell KL, Burford NT, Sum CS, Chen J et al.. (2016)
Evidence for Classical Cholinergic Toxicity Associated with Selective Activation of M1 Muscarinic Receptors.
J Pharmacol Exp Ther, 356 (2): 293-304. [PMID:26582730]
3. Kurimoto E, Matsuda S, Shimizu Y, Sako Y, Mandai T, Sugimoto T, Sakamoto H, Kimura H. (2018)
An Approach to Discovering Novel Muscarinic M1 Receptor Positive Allosteric Modulators with Potent Cognitive Improvement and Minimized Gastrointestinal Dysfunction.
J Pharmacol Exp Ther, 364 (1): 28-37. [PMID:29025977]