beroterkib   Click here for help

GtoPdb Ligand ID: 11727

Synonyms: ASTX-029 | ASTX029 | compound 15 [PMID: 34387469]
PDB Ligand
Compound class: Synthetic organic
Comment: ASTX029 is an orally bioavailable, clinical stage inhibitor of ERK1/2 kinases [1]. It was designed to inhibit the mitogen-activated protein kinase pathway in cancer cells. ASTX029 suppresses both ERK phosphorylation and enzymatic activity [2]. This was matched to the INN beroterkib (Proposed list 131, August 2024).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 125.91
Molecular weight 583.2
XLogP 3.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(F)cc(c1)[C@H](NC(=O)[C@H](N1Cc2c(C1=O)cc(cc2)c1nc(ncc1Cl)NC1CCOCC1)C)CO
Isomeric SMILES COc1cc(F)cc(c1)[C@@H](CO)NC(=O)[C@@H](C)N1Cc2ccc(cc2C1=O)c1nc(NC2CCOCC2)ncc1Cl
InChI InChI=1S/C29H31ClFN5O5/c1-16(27(38)34-25(15-37)19-9-20(31)12-22(10-19)40-2)36-14-18-4-3-17(11-23(18)28(36)39)26-24(30)13-32-29(35-26)33-21-5-7-41-8-6-21/h3-4,9-13,16,21,25,37H,5-8,14-15H2,1-2H3,(H,34,38)(H,32,33,35)/t16-,25-/m1/s1
InChI Key BVRGQPJKSKKGIH-PUAOIOHZSA-N
References
1. Heightman TD, Berdini V, Bevan L, Buck IM, Carr MG, Courtin A, Coyle JE, Day JEH, East C, Fazal L et al.. (2021)
Discovery of ASTX029, A Clinical Candidate Which Modulates the Phosphorylation and Catalytic Activity of ERK1/2.
J Med Chem, 64 (16): 12286-12303. [PMID:34387469]
2. Munck JM, Berdini V, Bevan L, Brothwood JL, Castro J, Courtin A, East C, Ferraldeschi R, Heightman TD, Hindley CJ et al.. (2021)
ASTX029, a Novel Dual-mechanism ERK Inhibitor, Modulates Both the Phosphorylation and Catalytic Activity of ERK.
Mol Cancer Ther, 20 (10): 1757-1768. [PMID:34330842]