BAY1238097   Click here for help

GtoPdb Ligand ID: 9119

Synonyms: BAY 1238097 | BAY-1238097
Compound class: Synthetic organic
Comment: BAY1238097 is a BET inhibitor [1,3]. BET inhibitors bind to the bromodomains of the bromodomain and extra-terminal motif (BET) proteins BRD2, BRD3, BRD4, and BRDT. This mechanism acts to prevent protein-protein interaction between BET proteins and acetylated histones and transcription factors. The action disrupts chromatin remodeling and inhibits expression of some growth-promoting genes which slows proliferation in susceptible tumours.
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 8
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 69.64
Molecular weight 451.56
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[C@H]1CC2=C(C=C(C(=C2)OC)OC)C(=NN1C(=O)NC)C3=CC=C(C=C3)N4CCN(C)CC4
Isomeric SMILES CNC(=O)N1N=C(C2=CC=C(C=C2)N3CCN(C)CC3)C4=CC(OC)=C(OC)C=C4C[C@@H]1C
InChI InChI=1S/C25H33N5O3/c1-17-14-19-15-22(32-4)23(33-5)16-21(19)24(27-30(17)25(31)26-2)18-6-8-20(9-7-18)29-12-10-28(3)11-13-29/h6-9,15-17H,10-14H2,1-5H3,(H,26,31)/t17-/m0/s1
InChI Key CJIPEACKIJJYED-KRWDZBQOSA-N
References
1. Gelato KA, Schöckel L, Klingbeil O, Rückert T, Lesche R, Toedling J, Kalfon E, Héroult M, Lejeune P, Mönning U et al.. (2018)
Super-enhancers define a proliferative PGC-1α-expressing melanoma subgroup sensitive to BET inhibition.
Oncogene, 37 (4): 512-521. [PMID:28991225]
2. Lejeune P et al.. 
Abstract 3524: BAY 1238097, a novel BET inhibitor with strong efficacy in hematological tumor models.
Accessed on 18/04/2016. Modified on 18/04/2016. http://cancerres.aacrjournals.org, http://cancerres.aacrjournals.org/content/75/15_Supplement/3524
3. Postel-Vinay S, Herbschleb K, Massard C, Woodcock V, Soria JC, Walter AO, Ewerton F, Poelman M, Benson N, Ocker M et al.. (2019)
First-in-human phase I study of the bromodomain and extraterminal motif inhibitor BAY 1238097: emerging pharmacokinetic/pharmacodynamic relationship and early termination due to unexpected toxicity.
Eur J Cancer, 109: 103-110. [PMID:30711772]