alloswitch-1   Click here for help

GtoPdb Ligand ID: 8543

Synonyms: trans-alloswitch-1
PDB Ligand
Compound class: Synthetic organic
Comment: Alloswitch-1 is the first reported photo-switchable negative allosteric modulator (NAM) for an endogenous G protein-coupled receptor [2], 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 [2]. 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 [2].
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 [1].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 75.94
Molecular weight 366.09
XLogP 5.12
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES COc1cc(N=Nc2ccccn2)ccc1NC(=O)c1ccccc1Cl
Isomeric SMILES COc1cc(/N=N/c2ccccn2)ccc1NC(=O)c1ccccc1Cl
InChI InChI=1S/C19H15ClN4O2/c1-26-17-12-13(23-24-18-8-4-5-11-21-18)9-10-16(17)22-19(25)14-6-2-3-7-15(14)20/h2-12H,1H3,(H,22,25)/b24-23+
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Synonyms Click here for help
Database Links Click here for help
Specialist databases
GPCRdb Ligand alloswitch-1
Other databases
GtoPdb PubChem SID 252166744
PubChem CID 76853680
Search Google for chemical match using the InChIKey JJRNGNCTPCWXGM-WCWDXBQESA-N
Search Google for chemicals with the same backbone JJRNGNCTPCWXGM
UniChem Compound Search for chemical match using the InChIKey JJRNGNCTPCWXGM-WCWDXBQESA-N
UniChem Connectivity Search for chemical match using the InChIKey JJRNGNCTPCWXGM-WCWDXBQESA-N