ulixertinib   Click here for help

GtoPdb Ligand ID: 9210

Synonyms: BVD-523 | VRT-752271
PDB Ligand
Compound class: Synthetic organic
Comment: Ulixertinib is an orally available, ATP-competitive inhibitor of the serine/threonine kinases extracellular signal-regulated kinase (ERK) 1 (MAPK3) and 2 (MAPK1), being investigated for anticancer activity in solid tumours and hematological malignancies carrying mutations in the MAPK signaling pathway, which renders them highly reliant on ERK for survival and growth. It is being developed by BioMed Valley Discoveries. This is one of the compounds claimed in patent WO2005113541 [1], where it is identified as I-9.
The INN record specifies the (1S) stereoisomer as ulixertinib.
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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 5
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 90.04
Molecular weight 432.11
XLogP 4.45
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 OCC(c1cccc(c1)Cl)NC(=O)c1[nH]cc(c1)c1cc(ncc1Cl)NC(C)C
Isomeric SMILES OC[C@H](c1cccc(c1)Cl)NC(=O)c1[nH]cc(c1)c1cc(ncc1Cl)NC(C)C
InChI InChI=1S/C21H22Cl2N4O2/c1-12(2)26-20-8-16(17(23)10-25-20)14-7-18(24-9-14)21(29)27-19(11-28)13-4-3-5-15(22)6-13/h3-10,12,19,24,28H,11H2,1-2H3,(H,25,26)(H,27,29)/t19-/m1/s1
InChI Key KSERXGMCDHOLSS-LJQANCHMSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[(1S)-1-(3-chlorophenyl)-2-hydroxyethyl]-4-[5-chloro-2-(propan-2-ylamino)pyridin-4-yl]-1H-pyrrole-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9969 ulixertinib
Synonyms Click here for help
BVD-523 | VRT-752271
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9657506
Reactome Reaction Reactome logo R-HSA-9657608
Other databases
CAS Registry No. 869886-67-9 (source: WHO INN record)
GtoPdb PubChem SID 315661286
PubChem CID 11719003
RCSB PDB Ligand EVK
Search Google for chemical match using the InChIKey KSERXGMCDHOLSS-LJQANCHMSA-N
Search Google for chemicals with the same backbone KSERXGMCDHOLSS
Search PubMed clinical trials ulixertinib
Search PubMed titles ulixertinib
Search PubMed titles/abstracts ulixertinib
UniChem Compound Search for chemical match using the InChIKey KSERXGMCDHOLSS-LJQANCHMSA-N
UniChem Connectivity Search for chemical match using the InChIKey KSERXGMCDHOLSS-LJQANCHMSA-N