MIDD0301   Click here for help

GtoPdb Ligand ID: 9890

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: MIDD0301 is a positive allosteric GABAAR modulator [1]. MIDD0301 targets specific GABA receptor subtypes (α4- and α5-containing receptors) that are selectively expressed in airway smooth muscle, airway epithelium, and inflammatory cells [2-3], and in this way offers the potential to alleviate asthma pathophysiology with a reduced likelihood of causing systemic side effects. It acts both as a bronchodilator and as an anti-inflammatory agent.
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 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 66.96
Molecular weight 413.02
XLogP 5.47
No. Lipinski's rules broken 1
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 Brc1ccc2c(c1)C(=NC(c1n2cnc1C(=O)O)C)c1ccccc1F
Isomeric SMILES Brc1ccc2c(c1)C(=N[C@@H](c1n2cnc1C(=O)O)C)c1ccccc1F
InChI InChI=1S/C19H13BrFN3O2/c1-10-18-17(19(25)26)22-9-24(18)15-7-6-11(20)8-13(15)16(23-10)12-4-2-3-5-14(12)21/h2-10H,1H3,(H,25,26)/t10-/m1/s1
InChI Key OSBXEAZWQGBYFU-SNVBAGLBSA-N
Classification Click here for help
Compound class Synthetic organic
Database Links Click here for help
GtoPdb PubChem SID 363894184
PubChem CID 133081966
Search Google for chemical match using the InChIKey OSBXEAZWQGBYFU-SNVBAGLBSA-N
Search Google for chemicals with the same backbone OSBXEAZWQGBYFU
UniChem Compound Search for chemical match using the InChIKey OSBXEAZWQGBYFU-SNVBAGLBSA-N
UniChem Connectivity Search for chemical match using the InChIKey OSBXEAZWQGBYFU-SNVBAGLBSA-N