ORM-12741   Click here for help

GtoPdb Ligand ID: 13129

Synonyms: DB105 | ORM 12741 | ORM12741
Compound class: Synthetic organic
Comment: ORM-12741 is a selective α2C-adrenoceptor antagonist.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 21.7
Molecular weight 285.38
XLogP 1.92
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
Click here for help

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/)

✖
Canonical SMILES C[C@@]1(CCCN2CCC3=C([C@H]12)OC4=C3C=CC=C4)COC
Isomeric SMILES C[C@@]1(CCCN2[C@@H]1C3=C(CC2)C4=CC=CC=C4O3)COC
InChI InChI=1S/C18H23NO2/c1-18(12-20-2)9-5-10-19-11-8-14-13-6-3-4-7-15(13)21-16(14)17(18)19/h3-4,6-7,17H,5,8-12H2,1-2H3/t17-,18-/m1/s1
InChI Key OCUKPFWNSAAHRP-QZTJIDSGSA-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. Herrick AL, Murray AK, Ruck A, Rouru J, Moore TL, Whiteside J, Hakulinen P, Wigley F, Snapir A. (2014)
A double-blind, randomized, placebo-controlled crossover trial of the α2C-adrenoceptor antagonist ORM-12741 for prevention of cold-induced vasospasm in patients with systemic sclerosis.
Rheumatology (Oxford), 53 (5): 948-52. [PMID:24489014]
2. Rinne JO, Wesnes K, Cummings JL, Hakulinen P, Hallikainen M, Hänninen J, Murphy M, Riordan H, Scheinin M, Soininen H et al.. (2017)
Tolerability of ORM-12741 and effects on episodic memory in patients with Alzheimer's disease.
Alzheimers Dement (N Y), 3 (1): 1-9. [PMID:29067315]
3. Shahid M, Rinne JO, Scheinin M, Virta J, Marjamäki P, Solin O, Arponen E, Sallinen J, Kuokkanen K, Rouru J. (2020)
Application of the PET ligand [11C]ORM-13070 to examine receptor occupancy by the α2C-adrenoceptor antagonist ORM-12741: translational validation of target engagement in rat and human brain.
EJNMMI Res, 10 (1): 152. [PMID:33296042]
4. Uys MM, Shahid M, Harvey BH. (2017)
Therapeutic Potential of Selectively Targeting the α2C-Adrenoceptor in Cognition, Depression, and Schizophrenia-New Developments and Future Perspective.
Front Psychiatry, 8: 144. [PMID:28855875]