ozanimod   Click here for help

GtoPdb Ligand ID: 8709

Synonyms: RPC-1063 | RPC1063 | Zeposia®
Approved drug PDB Ligand Immunopharmacology Ligand
ozanimod is an approved drug (EMA & FDA (2020))
Compound class: Synthetic organic
Comment: Ozanimod (RPC1063) is a novel, orally available, specific and potent agonist of the sphingosine 1-phosphate 1 receptor (S1P1R) and SIP5Rs [8]. Ozanimod is compound 86 in patent US20110172202 A1 [7], which specifies the (S)-enantiomer.
Ozanimod reduces chronic inflammation and alleviates kidney pathology in a mouse model of systemic lupus erythematosus (SLE), which suggests that ozanimod may offer clinical benefit as a SLE therapeutic [10].
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 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 104.2
Molecular weight 404.18
XLogP 3.73
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 OCCNC1CCc2c1cccc2c1noc(n1)c1ccc(c(c1)C#N)OC(C)C
Isomeric SMILES OCCN[C@H]1CCc2c1cccc2c1noc(n1)c1ccc(c(c1)C#N)OC(C)C
InChI InChI=1S/C23H24N4O3/c1-14(2)29-21-9-6-15(12-16(21)13-24)23-26-22(27-30-23)19-5-3-4-18-17(19)7-8-20(18)25-10-11-28/h3-6,9,12,14,20,25,28H,7-8,10-11H2,1-2H3/t20-/m0/s1
InChI Key XRVDGNKRPOAQTN-FQEVSTJZSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2020))
IUPAC Name Click here for help
5-[3-[(1S)-1-(2-hydroxyethylamino)-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxybenzonitrile
International Nonproprietary Names Click here for help
INN number INN
10057 ozanimod
Synonyms Click here for help
RPC-1063 | RPC1063 | Zeposia®
Database Links Click here for help
Specialist databases
GPCRdb Ligand ozanimod
Other databases
CAS Registry No. 1306760-87-1 (source: PubChem)
DrugCentral Ligand 5383
GtoPdb PubChem SID 252827367
PubChem CID 52938427
RCSB PDB Ligand JEU
Search Google for chemical match using the InChIKey XRVDGNKRPOAQTN-FQEVSTJZSA-N
Search Google for chemicals with the same backbone XRVDGNKRPOAQTN
Search PubMed clinical trials ozanimod
Search PubMed titles ozanimod
Search PubMed titles/abstracts ozanimod
UniChem Compound Search for chemical match using the InChIKey XRVDGNKRPOAQTN-FQEVSTJZSA-N
UniChem Connectivity Search for chemical match using the InChIKey XRVDGNKRPOAQTN-FQEVSTJZSA-N