UCSF7447   Click here for help

GtoPdb Ligand ID: 10666

Synonyms: Z1514261971 | ZINC000555417447
Compound class: Synthetic organic
Comment: UCSF7447 was found to act as selective inverse agonist of the melatonin receptor 1A (MT1 receptor) [1]. It represents a novel chemotype for MT ligands, and was designed using structure-based optimisation of a lead molecule that was identified in a docking screen of 150 million virtual molecules against a MT1 crystal structure.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 53.6
Molecular weight 361.99
XLogP 5.78
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(c(c1)Br)CNc1cccc(c1)c1nnc[nH]1
Isomeric SMILES Clc1ccc(c(c1)Br)CNc1cccc(c1)c1nnc[nH]1
InChI InChI=1S/C15H12BrClN4/c16-14-7-12(17)5-4-11(14)8-18-13-3-1-2-10(6-13)15-19-9-20-21-15/h1-7,9,18H,8H2,(H,19,20,21)
Bioactivity Comments
When administered at dusk, UCSF7447 advanced the phase of the circadian clock, in a MT1 receptor-dependent manner, in mice [1].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
MT1 receptor Hs Agonist Inverse agonist 7.3 pEC50 - 1
pEC50 7.3 (EC50 4.786x10-8 M) [1]
MT2 receptor Hs Agonist Inverse agonist 6.0 pEC50 - 1
pEC50 6.0 (EC50 1.024x10-6 M) [1]