vidofludimus   Click here for help

GtoPdb Ligand ID: 9860

Synonyms: 4SC-101 | IMU-838 (vidofludimus calcium) | SC12267
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vidofludimus (4SC-101) is a small molecule dihydroorotate dehydrogenase (DHOD) inhibitor that was developed for immunosuppressive potential [3]. It has an improved toxicity profile in comparison to the clinically used disease modifying anti-rheumatic drug (DMARD) leflunomide.
Since its initial development, vidofludimus has been superceded by IMU-838 which is an orally active polymorph of vidofludimus calcium (PubChem CID: 56944639) [5].SARS-CoV-2 and COVID-19: The target of vidofludimus, DHODH, plays a role in the metabolism of activated T cells and B cells to regulate the inflammatory response. It has been advanced to clinical trial in patients with severe COVID-19, to as attempt to block the release of pro-inflammatory cytokines and temper hyperinflammation in these patients.
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 6
Topological polar surface area 75.63
Molecular weight 355.12
XLogP 3.34
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 COc1cccc(c1)c1ccc(c(c1)F)NC(=O)C1=C(CCC1)C(=O)O
Isomeric SMILES COc1cccc(c1)c1ccc(c(c1)F)NC(=O)C1=C(CCC1)C(=O)O
InChI InChI=1S/C20H18FNO4/c1-26-14-5-2-4-12(10-14)13-8-9-18(17(21)11-13)22-19(23)15-6-3-7-16(15)20(24)25/h2,4-5,8-11H,3,6-7H2,1H3,(H,22,23)(H,24,25)
InChI Key XPRDUGXOWVXZLL-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[[2-fluoro-4-(3-methoxyphenyl)phenyl]carbamoyl]cyclopentene-1-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
9315 vidofludimus
Synonyms Click here for help
4SC-101 | IMU-838 (vidofludimus calcium) | SC12267
Database Links Click here for help
BindingDB Ligand 16111
CAS Registry No. 717824-30-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL197194
GtoPdb PubChem SID 363894154
PubChem CID 9820008
RCSB PDB Ligand D5H
Search Google for chemical match using the InChIKey XPRDUGXOWVXZLL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XPRDUGXOWVXZLL
Search PubMed clinical trials vidofludimus
Search PubMed titles vidofludimus
Search PubMed titles/abstracts vidofludimus
UniChem Compound Search for chemical match using the InChIKey XPRDUGXOWVXZLL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XPRDUGXOWVXZLL-UHFFFAOYSA-N