elsubrutinib   Click here for help

GtoPdb Ligand ID: 10464

Synonyms: example #30 (S) [WO2014210255A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Elsubrutinib (example #30 (S) [WO2014210255A1]) is the (S) stereoenantiomer of example #30 from Abbvie's patent WO2014210255A1 which claims BTK inhibitors for their potential to treat immunological and oncological conditions [1]. Example #30 (S) could be ABBV-105, an Abbvie BTK inhibitor that is being evaluated in combination with upadacitinib (ABT-494, a JAK1 inhibitor) in patients with rheumatoid arthritis or systemic lupus erythematosus (the combination is coded ABBV-599). Although preclinical efficacy has been reported [2], the structure of ABBV-105 has not been formally disclosed, so the name-to-structure alluded to here is speculative and provided in good faith.
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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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 79.19
Molecular weight 297.15
XLogP 1.86
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 C=CC(=O)N1CCCC(C1)c1ccc(c2c1cc[nH]2)C(=O)N
Isomeric SMILES C=CC(=O)N1CCC[C@H](C1)c1ccc(c2c1cc[nH]2)C(=O)N
InChI InChI=1S/C17H19N3O2/c1-2-15(21)20-9-3-4-11(10-20)12-5-6-14(17(18)22)16-13(12)7-8-19-16/h2,5-8,11,19H,1,3-4,9-10H2,(H2,18,22)/t11-/m1/s1
InChI Key UNHZLHSLZZWMNP-LLVKDONJSA-N
References
1. Bonafoux D, Davis HM, Frank KE, Friedman MM, Herold JM, Hoemann MZ, Huntley R, Osuma A, Sheppard G, Somal GK et al.. (2014)
Primary carboxamides as BTK inhibitors.
Patent number: WO2014210255A1. Assignee: Abbvie Inc.. Priority date: 26/06/2013. Publication date: 31/12/2014.
2. Goess C, Harris CM, Murdock S, McCarthy RW, Sampson E, Twomey R, Mathieu S, Mario R, Perham M, Goedken ER et al.. (2019)
ABBV-105, a selective and irreversible inhibitor of Bruton's tyrosine kinase, is efficacious in multiple preclinical models of inflammation.
Modern rheumatology, 29 (3): 510-522. [PMID:29862859]