vecabrutinib   Click here for help

GtoPdb Ligand ID: 10231

Synonyms: BIIB-062 | BIIB062 | SNS-062 | SNS062
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Vecabrutinib (SNS-062) is a second generation, noncovalent (reversible) Bruton's tyrosine kinase (BTK) inhibitor that is being developed by Sunesis Pharmaceuticals as a therapeutic for B cell malignancies that have developed resistance to first generation BTK inhibitors such as ibrutinib, through acquisition of the Cys481Ser mutation in the enzyme's active site. The structure presented here was obtained by searching PubChem using the IUPAC structure that was submitted to the WHO for the INN vecabrutinib. Sunesis' website associates the INN with the research code SNS-062 [3]. Formal name-to-structure identification and pharmacological analysis are yet to be disclosed in a peer-reviewed publication. Patent interrogation identifies example I-1 in Biogen/Sunesis' patent WO2013185084A1 as a structure match to vecabrutinib [1].
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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.

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View interactive charts of activity data across species
2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 130.47
Molecular weight 529.16
XLogP 3.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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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.

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Canonical SMILES Clc1cc(NC2CCCN(C2=O)C2CN(CCC2C(=O)N)c2ncnc(c2F)N)cc(c1)C(F)(F)F
Isomeric SMILES Clc1cc(N[C@@H]2CCCN(C2=O)[C@H]2CN(CC[C@@H]2C(=O)N)c2ncnc(c2F)N)cc(c1)C(F)(F)F
InChI InChI=1S/C22H24ClF4N7O2/c23-12-6-11(22(25,26)27)7-13(8-12)32-15-2-1-4-34(21(15)36)16-9-33(5-3-14(16)19(29)35)20-17(24)18(28)30-10-31-20/h6-8,10,14-16,32H,1-5,9H2,(H2,29,35)(H2,28,30,31)/t14-,15+,16-/m0/s1
InChI Key QLRRJMOBVVGXEJ-XHSDSOJGSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3R,3'R,4'S)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxo[1,3'-bipiperidine]-4'-carboxamide
International Nonproprietary Names Click here for help
INN number INN
10643 vecabrutinib
Synonyms Click here for help
BIIB-062 | BIIB062 | SNS-062 | SNS062
Database Links Click here for help
CAS Registry No. 1510829-06-7 (source: WHO INN record)
GtoPdb PubChem SID 381744913
PubChem CID 72547837
Search Google for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N
Search Google for chemicals with the same backbone QLRRJMOBVVGXEJ
Search PubMed clinical trials vecabrutinib
Search PubMed titles vecabrutinib
Search PubMed titles/abstracts vecabrutinib
UniChem Compound Search for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N
UniChem Connectivity Search for chemical match using the InChIKey QLRRJMOBVVGXEJ-XHSDSOJGSA-N