Ligand id: 8543

Name: alloswitch-1

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 75.94
Molecular weight 366.09
XLogP 5.68
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Compound class Synthetic organic
Database Links
PubChem CID 76853680
Search Google for chemical match using the InChIKey JJRNGNCTPCWXGM-WCWDXBQESA-N
Search Google for chemicals with the same backbone JJRNGNCTPCWXGM
Alloswitch-1 is the first reported photo-switchable negative allosteric modulator (NAM) for an endogenous G protein-coupled receptor [1], in this case a NAM of the mGlu5 metabotropic glutamate receptor. Violet light isomerizes the trans molecule to the cis molecule and green light reverses this isomerization [1]. In dark conditions trans-alloswitch-1 antagonizes IP production by quisqualate (orthosteric agonist)-activated mGlu5 receptors. Exposure to violet light reduces this level of antagonism, indicating that the cis-isomer is less active as a NAM than the trans-isomer [1].
The development of photo-switchable compounds is being pursued by pharmaceutical companies as a method to improve pharmacological selectivity by allowing precise spatio-temporal regulation of drug action.