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roluperidone   Click here for help

GtoPdb Ligand ID: 13306

Synonyms: Compound I [WO2020041504A1] | CYR-101 [4] | CYR101 | MIN-101 | MIN101
PDB Ligand
Compound class: Synthetic organic
Comment: Roluperidone (MIN-101; Minerva Neurosciences) has antagonist actions at 5-HT2A receptors, α1A- and α1B-adrenoceptors, and the sigma2 receptor (σ2). A crystal structure of roluperidone bound to the bovine σ2 has been reported [1].

roluperidone is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 40.62
Molecular weight 366.43
XLogP 1.13
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C1=CC2=C(C=C1)C(=O)N(CC3CCN(CC3)CC(=O)C4=CC=C(C=C4)F)C2
Isomeric SMILES C1CN(CCC1CN2CC3=CC=CC=C3C2=O)CC(=O)C4=CC=C(C=C4)F
InChI InChI=1S/C22H23FN2O2/c23-19-7-5-17(6-8-19)21(26)15-24-11-9-16(10-12-24)13-25-14-18-3-1-2-4-20(18)22(25)27/h1-8,16H,9-15H2
InChI Key RNRYULFRLCBRQS-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Alon A, Lyu J, Braz JM, Tummino TA, Craik V, O'Meara MJ, Webb CM, Radchenko DS, Moroz YS, Huang XP et al.. (2021)
Structures of the σ2 receptor enable docking for bioactive ligand discovery.
Nature, 600 (7890): 759-764. [PMID:34880501]
2. Davidson M, Saoud J, Staner C, Noel N, Luthringer E, Werner S, Reilly J, Schaffhauser JY, Rabinowitz J, Weiser M et al.. (2017)
Efficacy and Safety of MIN-101: A 12-Week Randomized, Double-Blind, Placebo-Controlled Trial of a New Drug in Development for the Treatment of Negative Symptoms in Schizophrenia.
Am J Psychiatry, 174 (12): 1195-1202. [PMID:28750582]
3. Davidson M, Saoud J, Staner C, Noel N, Werner S, Luthringer E, Walling D, Weiser M, Harvey PD, Strauss GP et al.. (2022)
Efficacy and Safety of Roluperidone for the Treatment of Negative Symptoms of Schizophrenia.
Schizophr Bull, 48 (3): 609-619. [PMID:35211743]
4. Luthringer RH, Pellegrini L, Karabelas AN. (2021)
Methods of use of cyclic amide derivatives to treat schizophrenia.
Patent number: WO2012012542A1. Assignee: Cyrenaic Pharmaceuticals. Priority date: 20/07/2020. Publication date: 26/01/2021.
5. Rabinowitz J, Staner C, Saoud J, Weiser M, Kuchibhatla R, Davidson M, Harvey PD, Luthringer R. (2023)
Long-term effects of Roluperidone on negative symptoms of schizophrenia.
Schizophr Res, 255: 9-13. [PMID:36933291]