pimasertib   Click here for help

GtoPdb Ligand ID: 7872

Synonyms: AS-703026 | AS703026 | MSC1936369B
PDB Ligand
Compound class: Synthetic organic
Comment: Pimasertib is an orally bioavailable small-molecule inhibitor of the mitogen-activated protein kinases MEK1 and MEK2 (MEK1/2) with potential antineoplastic activity [4]. It binds to an allosteric site, distinct from the ATP binding site [2] and as such prevents activation rather than inhibiting catalysis.
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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 4
Rotatable bonds 7
Topological polar surface area 94.48
Molecular weight 431.01
XLogP 1.66
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(CNC(=O)c1ccncc1Nc1ccc(cc1F)I)O
Isomeric SMILES OC[C@H](CNC(=O)c1ccncc1Nc1ccc(cc1F)I)O
InChI InChI=1S/C15H15FIN3O3/c16-12-5-9(17)1-2-13(12)20-14-7-18-4-3-11(14)15(23)19-6-10(22)8-21/h1-5,7,10,20-22H,6,8H2,(H,19,23)/t10-/m0/s1
InChI Key VIUAUNHCRHHYNE-JTQLQIEISA-N
References
1. Chang-Yew Leow C, Gerondakis S, Spencer A. (2013)
MEK inhibitors as a chemotherapeutic intervention in multiple myeloma.
Blood Cancer J, 3: e105. [PMID:23524590]
2. Goutopoulos A, Askew, BC, Bankston, D Clark, A, Dhanabal M, Dong R, Fischer D, Healey B, Jiang X, Josephson, K et al.. (2009)
AS703026: a novel allosteric MEK inhibitor. In: Proceedings of the 100th Annual Meeting of the American Association for Cancer Research; 2009 Apr 18-22; Denver, CO, Philadelphia (PA).
AACR,: Abstract 4776.
3. Kim K, Kong SY, Fulciniti M, Li X, Song W, Nahar S, Burger P, Rumizen MJ, Podar K, Chauhan D et al.. (2010)
Blockade of the MEK/ERK signalling cascade by AS703026, a novel selective MEK1/2 inhibitor, induces pleiotropic anti-myeloma activity in vitro and in vivo.
Br J Haematol, 149 (4): 537-49. [PMID:20331454]
4. Yoon J, Koo KH, Choi KY. (2011)
MEK1/2 inhibitors AS703026 and AZD6244 may be potential therapies for KRAS mutated colorectal cancer that is resistant to EGFR monoclonal antibody therapy.
Cancer Res, 71 (2): 445-53. [PMID:21118963]