alloswitch-1   Click here for help

GtoPdb Ligand ID: 8543

Synonyms: trans-alloswitch-1
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].
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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+
InChI Key JJRNGNCTPCWXGM-WCWDXBQESA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-chloro-N-{2-methoxy-4-[(E)-2-(pyridin-2-yl)diazen-1-yl]phenyl}benzamide
Synonyms Click here for help
trans-alloswitch-1
Database Links Click here for help
GtoPdb PubChem SID 252166744
PubChem CID 76853680
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