AS408   Click here for help

GtoPdb Ligand ID: 11074

PDB Ligand
Compound class: Synthetic organic
Comment: Allosteric modulator of the β2-adrenergic receptor.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 63.83
Molecular weight 314.02
XLogP 3.73
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES Brc1ccc2c(c1)c(N)nc(n2)Nc1ccccc1
Isomeric SMILES Brc1ccc2c(c1)c(N)nc(n2)Nc1ccccc1
InChI InChI=1S/C14H11BrN4/c15-9-6-7-12-11(8-9)13(16)19-14(18-12)17-10-4-2-1-3-5-10/h1-8H,(H3,16,17,18,19)
InChI Key MPGNABXYXOGUGH-UHFFFAOYSA-N
Bioactivity Comments
AS408 stabilizesan inactive conformation of the β2AR, and acts as a negative allosteric modulator for agonists and positive allosteric modulator for inverse agonists. Therefore, while AS408 is a NAM for agonist binding, G-protein activation and arrestin recruitment, AS408 is a modest PAM for binding to inverse agonists [1].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
β2-adrenoceptor N/A Allosteric modulator - - - - 1
⤷ [1]