acalabrutinib   Click here for help

GtoPdb Ligand ID: 8912

Synonyms: ACP-196 | Calquence® | Example 6 [US20140155385 A1] [2]
Approved drug PDB Ligand Immunopharmacology Ligand
acalabrutinib is an approved drug (FDA (2017), EMA (2020))
Compound class: Synthetic organic
Comment: Acalabrutinib is an orally available second-generation, selective and irreversible inhibitor of Bruton tyrosine kinase (BTK) [6], being investigated for its potential antineoplastic activity (in multiple haematologic malignancies and solid tumours), as well as a potential therapy for rheumatoid arthritis. Acalabrutinib covalently bonds to Cysteine-481 in BTK.
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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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Click here for structure editor
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 8
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 118.51
Molecular weight 465.19
XLogP 4.09
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 CC#CC(=O)N1CCCC1c1nc(c2n1ccnc2N)c1ccc(cc1)C(=O)Nc1ccccn1
Isomeric SMILES CC#CC(=O)N1CCC[C@H]1c1nc(c2n1ccnc2N)c1ccc(cc1)C(=O)Nc1ccccn1
InChI InChI=1S/C26H23N7O2/c1-2-6-21(34)32-15-5-7-19(32)25-31-22(23-24(27)29-14-16-33(23)25)17-9-11-18(12-10-17)26(35)30-20-8-3-4-13-28-20/h3-4,8-14,16,19H,5,7,15H2,1H3,(H2,27,29)(H,28,30,35)/t19-/m0/s1
InChI Key WDENQIQQYWYTPO-IBGZPJMESA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2017), EMA (2020))
IUPAC Name Click here for help
4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide
International Nonproprietary Names Click here for help
INN number INN
10150 acalabrutinib
Synonyms Click here for help
ACP-196 | Calquence® | Example 6 [US20140155385 A1] [2]
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678960
Reactome Reaction Reactome logo R-HSA-9679028
Other databases
CAS Registry No. 1420477-60-6 (source: INN record)
DrugCentral Ligand 5260
GtoPdb PubChem SID 310264693
PubChem CID 71226662
RCSB PDB Ligand XQQ
Search Google for chemical match using the InChIKey WDENQIQQYWYTPO-IBGZPJMESA-N
Search Google for chemicals with the same backbone WDENQIQQYWYTPO
Search PubMed clinical trials acalabrutinib
Search PubMed titles acalabrutinib
Search PubMed titles/abstracts acalabrutinib
UniChem Compound Search for chemical match using the InChIKey WDENQIQQYWYTPO-IBGZPJMESA-N
UniChem Connectivity Search for chemical match using the InChIKey WDENQIQQYWYTPO-IBGZPJMESA-N