varespladib   Click here for help

GtoPdb Ligand ID: 9657

Synonyms: compound 6m [PMID: 8978844] | LY315920 | S-5920 | varespladib methyl (A-002) | varespladib sodium (A-001)
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Varespladib (LY315920) is a secretory phospholipase A2 (sPLA2) inhibitor [1-2] in clinical development. The administered form can be varespladib sodium (A-001, for intravenuous administration) or varespladib methyl (A-002, for oral administration). The history of varespladib's discovery and development is summarized in [3].
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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 111.62
Molecular weight 380.14
XLogP 2.39
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 CCc1c(C(=O)C(=O)N)c2c(n1Cc1ccccc1)cccc2OCC(=O)O
Isomeric SMILES CCc1c(C(=O)C(=O)N)c2c(n1Cc1ccccc1)cccc2OCC(=O)O
InChI InChI=1S/C21H20N2O5/c1-2-14-19(20(26)21(22)27)18-15(9-6-10-16(18)28-12-17(24)25)23(14)11-13-7-4-3-5-8-13/h3-10H,2,11-12H2,1H3,(H2,22,27)(H,24,25)
InChI Key BHLXTPHDSZUFHR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-(1-benzyl-2-ethyl-3-oxamoylindol-4-yl)oxyacetic acid
International Nonproprietary Names Click here for help
INN number INN
8243 varespladib
Synonyms Click here for help
compound 6m [PMID: 8978844] | LY315920 | S-5920 | varespladib methyl (A-002) | varespladib sodium (A-001)
Database Links Click here for help
BindingDB Ligand 50055366
CAS Registry No. 172732-68-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL148674
GtoPdb PubChem SID 348353616
PubChem CID 155815
RCSB PDB Ligand VRD
Search Google for chemical match using the InChIKey BHLXTPHDSZUFHR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BHLXTPHDSZUFHR
Search PubMed clinical trials varespladib
Search PubMed titles varespladib
Search PubMed titles/abstracts varespladib
UniChem Compound Search for chemical match using the InChIKey BHLXTPHDSZUFHR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BHLXTPHDSZUFHR-UHFFFAOYSA-N