nivasorexant   Click here for help

GtoPdb Ligand ID: 12719

Synonyms: ACT-539313 | ACT539313
Compound class: Synthetic organic
Comment: Nivasorexant an orally active, selective and reversible orexin OX1 receptor antagonist (1-SORA). The chemical structure for nivasorexant matches that for Idorsia Pharmaceuticals' former clinical lead ACT-539313 [1]. ACT-539313's discovery was disclosed in February 2024 [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 85.46
Molecular weight 429.48
XLogP 3.01
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC1=CC=C(C(=C1)N2N=CC=N2)C(=O)N3CCOC[C@H]3CC4=CC=CC(=C4)N5N=CC=N5
Isomeric SMILES CC1=CC(=C(C=C1)C(=O)N2CCOC[C@H]2CC3=CC(=CC=C3)N4N=CC=N4)N5N=CC=N5
InChI InChI=1S/C23H23N7O2/c1-17-5-6-21(22(13-17)30-26-9-10-27-30)23(31)28-11-12-32-16-20(28)15-18-3-2-4-19(14-18)29-24-7-8-25-29/h2-10,13-14,20H,11-12,15-16H2,1H3/t20-/m1/s1
InChI Key GKPHAIOJCHBZCT-HXUWFJFHSA-N
References
1. Kaufmann P, Ort M, Golor G, Kornberger R, Dingemanse J. (2020)
First-in-human study with ACT-539313, a novel selective orexin-1 receptor antagonist.
Br J Clin Pharmacol, 86 (7): 1377-1386. [PMID:32067262]
2. Williams JT, Bolli MH, Brotschi C, Sifferlen T, Steiner MA, Treiber A, Gatfield J, Boss C. (2024)
Discovery of Nivasorexant (ACT-539313): The First Selective Orexin-1 Receptor Antagonist (SO1RA) Investigated in Clinical Trials.
J Med Chem, 67 (4): 2337-2348. [PMID:38331429]