ML385   Click here for help

GtoPdb Ligand ID: 10154

Synonyms: compound 2 [PMID: 27552339] | ML-385
Compound class: Synthetic organic
Comment: ML385 is a small molecule that binds to the Neh1 domain of the NRF2 transcription factor [6]. Activating mutations in NRF2 (and loss-of-function (LOF) mutations in KEAP1, a protein that binds NRF2 and targets it for proteosomal degradation) have been reported to facilitate cytoprotective functions which are associated with mechanisms of chemotherapy resistance and tumour expansion in various solid tumour types [2-5,8-9]. Evidence from preclinical and clinical studies has validated Inhibition of NRF2 as a novel mechanistic therapeutic approach for treatment-resistant tumours [1,7]. ML385 inhibits NRF2 activity in non-small cell lung cancer (NSCLC) cells with LOF KEAP1 mutations in vitro and inhibits tumour growth in xenograft models using KEAP1 mutant NSCLC cells (in combination with carboplatin) [6].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 109
Molecular weight 511.16
XLogP 4.38
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(Nc1sc(c(n1)c1ccc2c(c1)CCN2C(=O)c1ccccc1C)C)Cc1ccc2c(c1)OCO2
Isomeric SMILES O=C(Nc1sc(c(n1)c1ccc2c(c1)CCN2C(=O)c1ccccc1C)C)Cc1ccc2c(c1)OCO2
InChI InChI=1S/C29H25N3O4S/c1-17-5-3-4-6-22(17)28(34)32-12-11-20-15-21(8-9-23(20)32)27-18(2)37-29(31-27)30-26(33)14-19-7-10-24-25(13-19)36-16-35-24/h3-10,13,15H,11-12,14,16H2,1-2H3,(H,30,31,33)
InChI Key LINHYWKZVCNAMQ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-(1,3-benzodioxol-5-yl)-N-[5-methyl-4-[1-(2-methylbenzoyl)-2,3-dihydroindol-5-yl]-1,3-thiazol-2-yl]acetamide
Synonyms Click here for help
compound 2 [PMID: 27552339] | ML-385
Database Links Click here for help
CAS Registry No. 846557-71-9 (source: PubChem)
ChEMBL Ligand CHEMBL1479098
GtoPdb PubChem SID 381118864
PubChem CID 1383822
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Tocris
ML 385
Cat. No. 6243