RAMELTEON

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N05CH02
UNII 901AS54I69

Structure

InChI Key YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Smiles CCC(=O)NCC[C@@H]1CCc2ccc3c(c21)CCO3
InChI
InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H21NO2
Molecular Weight 259.35
AlogP 2.57
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 38.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Melatonin receptor agonist AGONIST FDA
Protein: Melatonin receptor
Description: Melatonin receptor type 1A
Organism : Homo sapiens
P48039 ENSG00000168412
Protein: Melatonin receptor
Description: Melatonin receptor type 1B
Organism : Homo sapiens
P49286 ENSG00000134640
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine-derivative receptor (family A GPCR) Melatonin receptor
- - - 0 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 113
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 85000 - - -
Assay Description Organism Bioactivity Reference
Binding affinity against human Melatonin receptor type 1A (MT1) in CHO cells None 0.0138 nM
Binding affinity against human Melatonin receptor type 1A (MT1) Homo sapiens 0.0138 nM
Binding affinity against human Melatonin receptor type 1B (MT2) Homo sapiens 0.045 nM
Inhibition of forskolin stimulated cAMP production in neonatal rat pituitary Rattus norvegicus 0.0208 nM
Binding affinity to rat MT1 receptor expressed in CHO-Galpha16 cells assessed as Ca2+ mobilization after 20 mins by FLIPR assay Rattus norvegicus 3.1 nM
Binding affinity to rat MT2 receptor expressed in CHO-Galpha16 cells assessed as Ca2+ mobilization after 20 mins by FLIPR assay Rattus norvegicus 0.89 nM
Displacement of [3H]melatonin from rat MT1 receptor expressed in CHO-Galpha16 cells Rattus norvegicus 2.0 nM
Displacement of [3H]melatonin from rat MT2 receptor expressed in CHO-Galpha16 cells Rattus norvegicus 0.03 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 127.58 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 113.38 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 4.23 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 27.76 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.38 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.665 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.17 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.26 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.02 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.26 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.17 %
Binding affinity to human MT1 expressed in CHO cells Homo sapiens 0.014 nM
Binding affinity to human MT2 expressed in CHO cells Homo sapiens 0.112 nM

Related Entries

Cross References

Resources Reference
ChEBI 109549
ChEMBL CHEMBL1218
DrugBank DB00980
DrugCentral 2355
FDA SRS 901AS54I69
Human Metabolome Database HMDB0015115
Guide to Pharmacology 1356
KEGG D02689
PDB JEV
PharmGKB PA164744896
PubChem 208902
SureChEMBL SCHEMBL29237
ZINC ZINC000003960338
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