EG00229   Click here for help

GtoPdb Ligand ID: 11335

Synonyms: compound 2 [PMID: 20151671] | EG-00229
PDB Ligand
Compound class: Synthetic organic
Comment: EG00229 is a small molecule inhibitor of the binding of VEGF-A165 to its receptor neuropilin 1 (NRP1) [2]. It was originally developed to block neo-vascularisation in tumours. EG00229 has subsequently been used to confirm that NRP1 is a host binding factor for both SARS-CoV and SARS-CoV-2 [1]. It binds directly to the NRP1 domain that binds to the furin-cleaved S1 fragment of the viral spike protein, and by blocking this interaction EG00229 has been shown to reduce viral infection in in vitro systems.
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 12
Hydrogen bond donors 6
Rotatable bonds 12
Topological polar surface area 265.11
Molecular weight 497.06
XLogP -0.23
No. Lipinski's rules broken 3
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 NC(=N)NCCC[C@@H](C(=O)O)NC(=O)c1sccc1NS(=O)(=O)c1cccc2c1nsn2
Isomeric SMILES NC(=N)NCCC[C@@H](C(=O)O)NC(=O)c1sccc1NS(=O)(=O)c1cccc2c1nsn2
InChI InChI=1S/C17H19N7O5S3/c18-17(19)20-7-2-4-11(16(26)27)21-15(25)14-10(6-8-30-14)24-32(28,29)12-5-1-3-9-13(12)23-31-22-9/h1,3,5-6,8,11,24H,2,4,7H2,(H,21,25)(H,26,27)(H4,18,19,20)/t11-/m0/s1
InChI Key ZWWMEDURALZMEV-NSHDSACASA-N
Classification Click here for help
Compound class Synthetic organic
Synonyms Click here for help
compound 2 [PMID: 20151671] | EG-00229
Database Links Click here for help
BindingDB Ligand 50313491
ChEMBL Ligand CHEMBL1078974
GtoPdb PubChem SID 440816704
PubChem CID 44631827
RCSB PDB Ligand 8DR
Search Google for chemical match using the InChIKey ZWWMEDURALZMEV-NSHDSACASA-N
Search Google for chemicals with the same backbone ZWWMEDURALZMEV
UniChem Compound Search for chemical match using the InChIKey ZWWMEDURALZMEV-NSHDSACASA-N
UniChem Connectivity Search for chemical match using the InChIKey ZWWMEDURALZMEV-NSHDSACASA-N