tasimelteon   Click here for help

GtoPdb Ligand ID: 7393

Synonyms: BMS-214778 | Hetlioz® | VEC-162
Approved drug
tasimelteon is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Tasimelteon is a melatonin receptor agonist, activating both the MT1 and MT2 receptor subtypes equipotently. Ramelteon and agomelatine are also melatonin receptor agonist class drugs.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 38.33
Molecular weight 245.14
XLogP 1.84
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCC(=O)NCC1CC1c1cccc2c1CCO2
Isomeric SMILES CCC(=O)NC[C@@H]1C[C@H]1c1cccc2c1CCO2
InChI InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1
Bioactivity Comments
Tasimelteon is a non-selective MT1/MT2 receptor ligand, with low nanomolar affinities for the human receptors.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MT2 receptor Primary target of this compound Hs Agonist Full agonist 10.2 pKi - 1-2
pKi 10.2 (Ki 6.92x10-11 M) [1-2]
MT1 receptor Primary target of this compound Hs Agonist Full agonist 9.5 pKi - 1-2
pKi 9.5 (Ki 3.04x10-10 M) [1-2]
Ligand mentioned in the following text fields