SB269652   

GtoPdb Ligand ID: 7694

Synonyms: SB-269,652 | SB-269652
Compound class: Synthetic organic
Comment: SB269652 was originally described as an allosteric antagonist at dopamine D3 and D2 receptors [4]. Further analysis has revealed a novel mechanism of allostery, which relies on the presence of receptor dimers [2]. SB269652 acts as a bitopic ligand [3], with one pharmacophore binding to one receptor protomer and the other pharmacophore allosterically modulating the binding of a ligand on the second partner in the dimer, in this instance rendering the compound a negative allosteric regulator of dopamine binding to the D2 receptor [2].
PubChem CID 9910352 represents the compound structure without specified stereochemistry.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 71.92
Molecular weight 426.24
XLogP 4.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1ccc2c(c1)CN(CC2)CCC1CCC(CC1)NC(=O)c1cc2c([nH]1)cccc2
Isomeric SMILES N#Cc1ccc2c(c1)CN(CC2)CC[C@@H]1CC[C@H](CC1)NC(=O)c1cc2c([nH]1)cccc2
InChI InChI=1S/C27H30N4O/c28-17-20-5-8-21-12-14-31(18-23(21)15-20)13-11-19-6-9-24(10-7-19)29-27(32)26-16-22-3-1-2-4-25(22)30-26/h1-5,8,15-16,19,24,30H,6-7,9-14,18H2,(H,29,32)/t19-,24-
InChI Key JGLGOAQPUQITLD-OGAOHHHESA-N
Classification
Compound class Synthetic organic
IUPAC Name
N-[(1r,4r)-4-[2-(7-cyano-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]cyclohexyl]-1H-indole-2-carboxamide
Synonyms
SB-269,652 | SB-269652
Database Links
ChEMBL Ligand CHEMBL2219578
GtoPdb PubChem SID 223366027
PubChem CID 9910352
PubChem SID 184696710
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