ulotaront   Click here for help

GtoPdb Ligand ID: 10454

Synonyms: example 129 [WO2011069063A2] [6] | SEP-363856 (parent molecule) | SEP-856 | SEP363856
Compound class: Synthetic organic
Comment: Ulotaront (SEP-363856) is an orally active and brain-penetrant psychotropic agent with a novel mechanism of action. It acts as a trace amine-associated receptor 1 (TAAR1) agonist with additional 5-HT1A receptor agonist activity, and agonism at both of these receptors appears to be required for its clinical effects [2-3]. SEP-363856 is being developed by Sunovion Pharmaceuticals and PsychoGenics, and was granted FDA Breakthrough Therapy Designation as an anti-schizophrenia therapeutic in May 2019. The lack of D2 receptor activity distinguishes SEP-363856 from current antipsychotic medications.
In the Dedic et al. article from 2019 SEP-363856 refers to the hydrochloride salt. We show the parent molecule here. This S enantiomer is more active at TAAR1 compared to the R stereoenantiomer [2].
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

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

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.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 49.5
Molecular weight 183.07
XLogP 0.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES CNCC1OCCc2c1scc2
Isomeric SMILES CNC[C@@H]1OCCc2c1scc2
InChI InChI=1S/C9H13NOS/c1-10-6-8-9-7(2-4-11-8)3-5-12-9/h3,5,8,10H,2,4,6H2,1H3/t8-/m0/s1
InChI Key ABDDQTDRAHXHOC-QMMMGPOBSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-[(7S)-5,7-dihydro-4H-thieno[2,3-c]pyran-7-yl]-N-methylmethanamine
International Nonproprietary Names Click here for help
INN number INN
11319 ulotaront
Synonyms Click here for help
example 129 [WO2011069063A2] [6] | SEP-363856 (parent molecule) | SEP-856 | SEP363856
Database Links Click here for help
Specialist databases
GPCRdb Ligand ulotaront
Other databases
GtoPdb PubChem SID 385612214
PubChem CID 89532783
Search Google for chemical match using the InChIKey ABDDQTDRAHXHOC-QMMMGPOBSA-N
Search Google for chemicals with the same backbone ABDDQTDRAHXHOC
Search PubMed clinical trials ulotaront
Search PubMed titles ulotaront
Search PubMed titles/abstracts ulotaront
UniChem Compound Search for chemical match using the InChIKey ABDDQTDRAHXHOC-QMMMGPOBSA-N
UniChem Connectivity Search for chemical match using the InChIKey ABDDQTDRAHXHOC-QMMMGPOBSA-N