ramelteon   Click here for help

GtoPdb Ligand ID: 1356

Synonyms: Rozerem® | TAK-375 | TAK375
Approved drug PDB Ligand
ramelteon is an approved drug (FDA (2005))
Compound class: Synthetic organic
Comment: Ramelteon is a non-selective melatonin receptor agonist.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

ramelteon is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 38.33
Molecular weight 259.16
XLogP 2.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC(=O)NCCC1CCc2c1c1CCOc1cc2
Isomeric SMILES CCC(=O)NCC[C@@H]1CCc2c1c1CCOc1cc2
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
InChI Key YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2005))
IUPAC Name Click here for help
N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e][1]benzoxol-8-yl]ethyl]propanamide
International Nonproprietary Names Click here for help
INN number INN
8447 ramelteon
Synonyms Click here for help
Rozerem® | TAK-375 | TAK375
Database Links Click here for help
Specialist databases
GPCRdb Ligand ramelteon
Other databases
BindingDB Ligand 50118470
CAS Registry No. 196597-26-9
ChEBI CHEBI:321962
ChEMBL Ligand CHEMBL1218
DrugBank Ligand DB00980
DrugCentral Ligand 2355
GtoPdb PubChem SID 135651228
PubChem CID 208902
RCSB PDB Ligand JEV
Search Google for chemical match using the InChIKey YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Search Google for chemicals with the same backbone YLXDSYKOBKBWJQ
Search PubMed clinical trials ramelteon
Search PubMed titles ramelteon
Search PubMed titles/abstracts ramelteon
UniChem Compound Search for chemical match using the InChIKey YLXDSYKOBKBWJQ-LBPRGKRZSA-N
UniChem Connectivity Search for chemical match using the InChIKey YLXDSYKOBKBWJQ-LBPRGKRZSA-N
Wikipedia Ramelteon

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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Tocris
TAK 375 (links to external site)
Cat. No. 6777