darizmetinib   Click here for help

GtoPdb Ligand ID: 12376

Synonyms: example 63 [WO2019149738A1]
Compound class: Synthetic organic
Comment: This is the chemical structure for the INN darizmetinib. This structure is claimed in HepaRegeniX's patent WO2019149738A1, as a mitogen-activated protein kinase kinase 4 (MKK4) inhibitor [1]. We suspect that darizmetinib is HepaRegeniX's lead MKK4 inhibitor HRX-0215, that has entered phase 1 clinical trial, although name>structure for HRX-0215 has not been formally disclosed (Feb 2023). MKK4 is a key regulator of liver regeneration. Inhibition of MKK4 promotes the regenerative capacity of hepatocytes.
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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 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 126.08
Molecular weight 457.1
XLogP 3.83
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 CCCS(=O)(=O)Nc1c(F)ccc(c1F)C(=O)c1[nH]nc2c1cc(cn2)c1ccncc1
Isomeric SMILES CCCS(=O)(=O)Nc1c(ccc(c1F)C(=O)c1c2cc(cnc2n[nH]1)c1ccncc1)F
InChI InChI=1S/C21H17F2N5O3S/c1-2-9-32(30,31)28-19-16(22)4-3-14(17(19)23)20(29)18-15-10-13(11-25-21(15)27-26-18)12-5-7-24-8-6-12/h3-8,10-11,28H,2,9H2,1H3,(H,25,26,27)
InChI Key WBNMARNYIFMNEP-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[2,6-difluoro-3-(5-pyridin-4-yl-2H-pyrazolo[3,4-b]pyridine-3-carbonyl)phenyl]propane-1-sulfonamide
International Nonproprietary Names Click here for help
INN number INN
12490 darizmetinib
Synonyms Click here for help
example 63 [WO2019149738A1]
Database Links Click here for help
CAS Registry No. 2369583-33-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL4795907
GtoPdb PubChem SID 479821167
PubChem CID 139369660
Search Google for chemical match using the InChIKey WBNMARNYIFMNEP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone WBNMARNYIFMNEP
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UniChem Compound Search for chemical match using the InChIKey WBNMARNYIFMNEP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey WBNMARNYIFMNEP-UHFFFAOYSA-N