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atebimetinib   Click here for help

GtoPdb Ligand ID: 13733

Synonyms: compound 9 [US20230119327A1]
Compound class: Synthetic organic
Comment: The chemical structure for atebimetinib was derived from WHO proposed INN list 132 (Feb 2025), in which it is listed as a MEK tyrosine kinase inhibitor with antineoplastic potential. The structure is claimed in patent US20230119327A1 (Immuneering Corp) [1]. Immuneering have a MEK inhibitor called IMM-1-104 as a lead asset in their development pipeline. IMM-1-104 is designed to inhibit MEK and ERK phosphorylation downstream of RAS, to achieve robust MAPK pathway inhibition irrespective of the oncogenic RAS mutation present in the tumour.
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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 10
Topological polar surface area 139.49
Molecular weight 505.54
XLogP -1.15
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CNS(=O)(=O)NC1=C(C(=CC=C1)CC2=C(CN(C)C)C3=C(C=C(C=C3)CN(C)C(=O)[O-])OC2=O)F
Isomeric SMILES CN(C)CC1=C(C(OC2=C1C=CC(=C2)CN(C([O-])=O)C)=O)CC3=C(C(=CC=C3)NS(NC)(=O)=O)F
InChI InChI=1S/C23H27FN4O6S/c1-25-35(32,33)26-19-7-5-6-15(21(19)24)11-17-18(13-27(2)3)16-9-8-14(12-28(4)23(30)31)10-20(16)34-22(17)29/h5-10,25-26H,11-13H2,1-4H3,(H,30,31)/p-1
InChI Key QIMAJRSGTYJBIS-UHFFFAOYSA-M

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-({4-[(dimethylamino)methyl]-3-({2-fluoro-3-[(methylsulfamoyl)amino]phenyl}methyl)-2-oxo-2H-chromen-7-yl}methyl)-N-methylcarbamate
International Nonproprietary Names Click here for help
INN number INN
13383 atebimetinib
Synonyms Click here for help
compound 9 [US20230119327A1]
Database Links Click here for help
CAS Registry No. 2669009-92-9 (source: WHO INN record)
GtoPdb PubChem SID 513757515
PubChem CID 168111901
Search Google for chemical match using the InChIKey QIMAJRSGTYJBIS-UHFFFAOYSA-M
Search Google for chemicals with the same backbone QIMAJRSGTYJBIS
Search PubMed clinical trials atebimetinib
Search PubMed titles atebimetinib
Search PubMed titles/abstracts atebimetinib
UniChem Compound Search for chemical match using the InChIKey QIMAJRSGTYJBIS-UHFFFAOYSA-M
UniChem Connectivity Search for chemical match using the InChIKey QIMAJRSGTYJBIS-UHFFFAOYSA-M