fenebrutinib   Click here for help

GtoPdb Ligand ID: 9299

Synonyms: Example 130 [US20140194408] | GDC-0853 | GDC0853 | RG-7845 | RG7845
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Fenebrutinib (RG7845, GDC-0853) is a reversible Bruton's tyrosine kinase (BTK) inhibitor, under investigation for therapeutic potential in difficult-to-treat autoimmune diseases, including multiple sclerosis [7]. The compound is claimed in patent WO2013067274 [2].
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 10
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 120.99
Molecular weight 664.35
XLogP 5.44
No. Lipinski's rules broken 1
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 OCc1c(ccnc1N1CCn2c(C1=O)cc1c2CC(C1)(C)C)c1cc(Nc2ccc(cn2)N2CCN(CC2C)C2COC2)c(=O)n(c1)C
Isomeric SMILES OCc1c(ccnc1N1CCn2c(C1=O)cc1c2CC(C1)(C)C)c1cc(Nc2ccc(cn2)N2CCN(C[C@@H]2C)C2COC2)c(=O)n(c1)C
InChI InChI=1S/C37H44N8O4/c1-23-18-42(27-21-49-22-27)9-10-43(23)26-5-6-33(39-17-26)40-30-13-25(19-41(4)35(30)47)28-7-8-38-34(29(28)20-46)45-12-11-44-31(36(45)48)14-24-15-37(2,3)16-32(24)44/h5-8,13-14,17,19,23,27,46H,9-12,15-16,18,20-22H2,1-4H3,(H,39,40)/t23-/m0/s1
InChI Key WNEODWDFDXWOLU-QHCPKHFHSA-N
Immunopharmacology Comments
BTK is teh key kinase in the B cell receptor signalling cascade. It acts downstream of Syk and amplifies signals from immunoreceptor tyrosine-based activation motif (ITAM)-containing receptors to mediate NF-κB activation. BTK is overexpressed or hyperactivated in a number of autoimmune diseases and cancers [1,6], and is a validated drug target for these indications. Fenebrutinib is a clinical candidate for hard to treat autoimmune diseases.
Immunopharmacology Disease
Disease X-Refs Comment References
Systemic lupus erythematosus Disease Ontology: DOID:9074
OMIM: 152700
Orphanet: ORPHA536
 Phase 2 clinical candidate for SLE (see NCT02908100).
Rheumatoid arthritis Disease Ontology: DOID:7148
OMIM: 180300
 Phase 2 clinical candidate for RA (see NCT02983227 and NCT02833350).
B-cell lymphoma Disease Ontology: DOID:707
 Phase 2 clinical candidate for B cell lymphoma (see NCT01991184).
B-cell chronic lymphocytic leukemia OMIM: 151400
Orphanet: ORPHA67038
 Phase 2 clinical candidate for CLL (see NCT01991184).