BIX-01294   Click here for help

GtoPdb Ligand ID: 7014

Synonyms: BIX 01294 | BIX01294
PDB Ligand
Compound class: Synthetic organic
Comment: BIX-01294 is a histone methyltransferase inhibitor [1,3].
BIX-01294-induced inhibition of H3K9me2 levels and upregulation of schizophrenia candidate gene expression suggests some therapeutic potential for histone modifying pharmacology in the treatment of schizophrenia [2].
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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 6
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 65.99
Molecular weight 490.31
XLogP 4.18
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 COc1cc2nc(nc(c2cc1OC)NC1CCN(CC1)Cc1ccccc1)N1CCCN(CC1)C
Isomeric SMILES COc1cc2nc(nc(c2cc1OC)NC1CCN(CC1)Cc1ccccc1)N1CCCN(CC1)C
InChI InChI=1S/C28H38N6O2/c1-32-12-7-13-34(17-16-32)28-30-24-19-26(36-3)25(35-2)18-23(24)27(31-28)29-22-10-14-33(15-11-22)20-21-8-5-4-6-9-21/h4-6,8-9,18-19,22H,7,10-17,20H2,1-3H3,(H,29,30,31)
InChI Key OSXFATOLZGZLSK-UHFFFAOYSA-N
References
1. Chang Y, Zhang X, Horton JR, Upadhyay AK, Spannhoff A, Liu J, Snyder JP, Bedford MT, Cheng X. (2009)
Structural basis for G9a-like protein lysine methyltransferase inhibition by BIX-01294.
Nat Struct Mol Biol, 16 (3): 312-7. [PMID:19219047]
2. Chase KA, Feiner B, Ramaker MJ, Hu E, Rosen C, Sharma RP. (2019)
Examining the effects of the histone methyltransferase inhibitor BIX-01294 on histone modifications and gene expression in both a clinical population and mouse models.
PLoS ONE, 14 (6): e0216463. [PMID:31185023]
3. Kubicek S, O'Sullivan RJ, August EM, Hickey ER, Zhang Q, Teodoro ML, Rea S, Mechtler K, Kowalski JA, Homon CA et al.. (2007)
Reversal of H3K9me2 by a small-molecule inhibitor for the G9a histone methyltransferase.
Mol Cell, 25 (3): 473-81. [PMID:17289593]