VU0486846   Click here for help

GtoPdb Ligand ID: 12305

Synonyms: compound 16 [PMID: 29701957]
Compound class: Synthetic organic
Comment: VU0486846 is a positive allosteric modulator of M1 muscarinic acetylcholine receptors [1]. Activation of M1 receptors by such compounds is proposed to improve cognition in conditions that are associated with cholinergic deficit such as schizophrenia, and Alzheimer's and Parkinson's diseases. VU0486846 exhibits very weak M1 agonist activity in vitro and is inactive in the prefrontal cortex and does not induce cholinergic adverse effects in vivo.
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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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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 2
Rotatable bonds 6
Topological polar surface area 79.1
Molecular weight 432.22
XLogP 4.2
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 O[C@H]1CCCC[C@@H]1NC(=O)[C@@H]1Oc2ccccc2N(C1)Cc1ccc(cc1)n1cccn1
Isomeric SMILES C1CC[C@@H]([C@H](C1)NC(=O)[C@H]1CN(c2ccccc2O1)Cc1ccc(cc1)n1cccn1)O
InChI InChI=1S/C25H28N4O3/c30-22-8-3-1-6-20(22)27-25(31)24-17-28(21-7-2-4-9-23(21)32-24)16-18-10-12-19(13-11-18)29-15-5-14-26-29/h2,4-5,7,9-15,20,22,24,30H,1,3,6,8,16-17H2,(H,27,31)/t20-,22-,24+/m0/s1
InChI Key LZCHTDQRMCSDSE-ODGPQVTHSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-N-[(1S,2S)-2-hydroxycyclohexyl]-4-[(4-pyrazol-1-ylphenyl)methyl]-2,3-dihydro-1,4-benzoxazine-2-carboxamide
Synonyms Click here for help
compound 16 [PMID: 29701957]
Database Links Click here for help
Specialist databases
GPCRdb Ligand VU0486846
Other databases
BindingDB Ligand 50273248
CAS Registry No. 1788055-11-7 (source: PubChem)
GtoPdb PubChem SID 479821096
PubChem CID 118124117
Search Google for chemical match using the InChIKey LZCHTDQRMCSDSE-ODGPQVTHSA-N
Search Google for chemicals with the same backbone LZCHTDQRMCSDSE
UniChem Compound Search for chemical match using the InChIKey LZCHTDQRMCSDSE-ODGPQVTHSA-N
UniChem Connectivity Search for chemical match using the InChIKey LZCHTDQRMCSDSE-ODGPQVTHSA-N