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 Bruton's tyrosine kinase (BTK) inhibitor, under investigation for therapeutic potential in difficult-to-treat autoimmune diseases. 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
References
1. Akinleye A, Chen Y, Mukhi N, Song Y, Liu D. (2013)
Ibrutinib and novel BTK inhibitors in clinical development.
J Hematol Oncol, 6: 59. [PMID:23958373]
2. Crawford JJ, Ortwine DF, Wei B, Young WB. (2013)
Heteroaryl pyridone and aza-pyridone compounds as inhibitors of btk activity.
Patent number: WO2013067274. Assignee: Genentech, Inc.. Priority date: 03/11/2011. Publication date: 10/05/2013.
3. Musumeci F, Sanna M, Greco C, Giacchello I, Fallacara AL, Amato R, Schenone S. (2017)
Pyrrolo[2,3-d]pyrimidines active as Btk inhibitors.
Expert Opin Ther Pat, 27 (12): 1305-1318. [PMID:28705083]