UCM1014   Click here for help

GtoPdb Ligand ID: 9226

Synonyms: Compound 8a [PMID 26334942]
Compound class: Synthetic organic
Comment: Molecular superpositions on previously developed pharmacophore models predicted a suitable position for a methoxy group on a tetrahydroquinoline ring. This lead to the optimisation of a benzyl derivative 8a (UCM1014) with a melatonin receptor MT2 Ki of 0.001 nM and more than 10000-fold selectivity over MT1, as a full agonist tool compound [2]. This is compared with other modulators in a recent melatonin receptor review [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 41.57
Molecular weight 338.2
XLogP 3.97
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)NCC1CCc2c(N1Cc1ccccc1)cccc2OC
Isomeric SMILES CCC(=O)NCC1CCc2c(N1Cc1ccccc1)cccc2OC
InChI InChI=1S/C21H26N2O2/c1-3-21(24)22-14-17-12-13-18-19(10-7-11-20(18)25-2)23(17)15-16-8-5-4-6-9-16/h4-11,17H,3,12-15H2,1-2H3,(H,22,24)
1. Boscardin E, Alijevic O, Hummler E, Frateschi S, Kellenberger S. (2016)
The function and regulation of acid-sensing ion channels (ASICs) and the epithelial Na(+) channel (ENaC): IUPHAR Review 19.
Br J Pharmacol, 173 (18): 2671-701. [PMID:27278329]
2. Spadoni G, Bedini A, Lucarini S, Mari M, Caignard DH, Boutin JA, Delagrange P, Lucini V, Scaglione F, Lodola A et al.. (2015)
Highly Potent and Selective MT2 Melatonin Receptor Full Agonists from Conformational Analysis of 1-Benzyl-2-acylaminomethyl-tetrahydroquinolines.
J Med Chem, 58 (18): 7512-25. [PMID:26334942]