compound 1 [PMID: 33547286]   Click here for help

GtoPdb Ligand ID: 11447

PDB Ligand
Compound class: Synthetic organic
Comment: Compound 1 is a small molecule orexin receptor agonist, with selectivity for OX2 [1]. Cryo-EM reveals that it binds to the orthosteric pocket of the OX2 receptor and stabilises the active receptor conformation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 143.38
Molecular weight 624.22
XLogP 5.9
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc(cc1S(=O)(=O)Nc1cccc(c1)CCNC(=O)c1ccccc1n1nccn1)c1cccc(c1)C(=O)N(C)C
Isomeric SMILES COc1ccc(cc1S(=O)(=O)Nc1cccc(c1)CCNC(=O)c1ccccc1n1nccn1)c1cccc(c1)C(=O)N(C)C
InChI InChI=1S/C33H32N6O5S/c1-38(2)33(41)26-10-7-9-24(21-26)25-14-15-30(44-3)31(22-25)45(42,43)37-27-11-6-8-23(20-27)16-17-34-32(40)28-12-4-5-13-29(28)39-35-18-19-36-39/h4-15,18-22,37H,16-17H2,1-3H3,(H,34,40)
InChI Key AMTAVIZAVFJXIJ-UHFFFAOYSA-N
References
1. Hong C, Byrne NJ, Zamlynny B, Tummala S, Xiao L, Shipman JM, Partridge AT, Minnick C, Breslin MJ, Rudd MT et al.. (2021)
Structures of active-state orexin receptor 2 rationalize peptide and small-molecule agonist recognition and receptor activation.
Nat Commun, 12 (1): 815. [PMID:33547286]