compound 2 [PMID: 28621538]   Click here for help

GtoPdb Ligand ID: 11282

Synonyms: example 727 [WO2012093101A1]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 2 is a small molecule complement factor D inhibitor that has been developed by Novartis [1]. The compound is orally bioavailable, and blocks activation of the complement alternative pathway in vitro and in vivo. Factor D inhibitors act upstream of the factor C5-targeting drugs such as eculizumab and ravulizumab, and small molecules are intended to offer more flexible therapeutic options than the existing monoclonal antibodies.
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 8
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 123.21
Molecular weight 482.07
XLogP 1.84
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 Brc1cccc(n1)NC(=O)[C@@H]1C[C@@H]2[C@H](N1C(=O)Cn1nc(c3c1cccc3)C(=O)N)C2
Isomeric SMILES Brc1cccc(n1)NC(=O)[C@@H]1C[C@@H]2[C@H](N1C(=O)Cn1nc(c3c1cccc3)C(=O)N)C2
InChI InChI=1S/C21H19BrN6O3/c22-16-6-3-7-17(24-16)25-21(31)15-9-11-8-14(11)28(15)18(29)10-27-13-5-2-1-4-12(13)19(26-27)20(23)30/h1-7,11,14-15H,8-10H2,(H2,23,30)(H,24,25,31)/t11-,14-,15+/m1/s1
InChI Key CWZUTHDJLNZLCM-DFBGVHRSSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-[2-[(1R,3S,5R)-3-[(6-bromopyridin-2-yl)carbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]indazole-3-carboxamide
Synonyms Click here for help
example 727 [WO2012093101A1]
Database Links Click here for help
BindingDB Ligand 171350
ChEMBL Ligand CHEMBL3683753
GtoPdb PubChem SID 434321717
PubChem CID 86673884
RCSB PDB Ligand 8NQ
Search Google for chemical match using the InChIKey CWZUTHDJLNZLCM-DFBGVHRSSA-N
Search Google for chemicals with the same backbone CWZUTHDJLNZLCM
UniChem Compound Search for chemical match using the InChIKey CWZUTHDJLNZLCM-DFBGVHRSSA-N
UniChem Connectivity Search for chemical match using the InChIKey CWZUTHDJLNZLCM-DFBGVHRSSA-N