bentamapimod   Click here for help

GtoPdb Ligand ID: 9926

Synonyms: AS-602801 | AS602801 | PGL-5001 | PGL5001
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Bentamapimod (a.k.a. PGL-5001 and AS602801) is novel and orally active Jun kinase inhibitor (JNK1= MAPK8 and JNK2= MAPK9). It has shown preclinical efficacy that may be applied to the treatment of endometriotic lesions [1,3]. It also inhibits cancer stem cells in vitro and in vivo [2]. It was originally developed by Merck Seroneo (JNK-I AS602801) and then in-licensed by PregLem and re-named PGL5001 (PGL5 may also be used).
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 0
Rotatable bonds 7
Topological polar surface area 112.4
Molecular weight 457.16
XLogP 2.27
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 N#CC(c1nc2c(s1)cccc2)c1ccnc(n1)OCc1ccc(cc1)CN1CCOCC1
Isomeric SMILES N#CC(c1nc2c(s1)cccc2)c1ccnc(n1)OCc1ccc(cc1)CN1CCOCC1
InChI InChI=1S/C25H23N5O2S/c26-15-20(24-28-22-3-1-2-4-23(22)33-24)21-9-10-27-25(29-21)32-17-19-7-5-18(6-8-19)16-30-11-13-31-14-12-30/h1-10,20H,11-14,16-17H2
InChI Key XCPPIJCBCWUBNT-UHFFFAOYSA-N
Bioactivity Comments
Bentamapimod is likely one of the compounds claimed in Merck Serono's patent US20130267512A1, as the SMILES string returns this patent via a SureChEMBL open patent search. No potency data is provided in the patent for the direct inhibition of the JNK kinases, so we are unable to validate the compound's primary molecular target, pending publication in peer reviewed literature.