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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
InChI Key PTOIAAWZLUQTIO-GXFFZTMASA-N
Bioactivity Comments
Tasimelteon is a non-selective MT1/MT2 receptor ligand, with low nanomolar affinities for the human receptors.
Selectivity at GPCRs
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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