DASA-58   Click here for help

GtoPdb Ligand ID: 10556

Synonyms: compound 1 [PMID: 21958545] | DASA58 | ML-203 | ML203
PDB Ligand
Compound class: Synthetic organic
Comment: DASA-58 is an activator of tumour-associated pyruvate kinase M2 (PKM2) [2]. PKM2 activation has potential to interfere with the anabolic metabolic pathway that is utilised by cancer cells to maintain high levels of proliferation. Like TEPP-46, DASA-58 promotes formation of highly active PKM2 tetramers and suppresses tumour expansion in vivo [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 136
Molecular weight 453.1
XLogP 0.69
No. Lipinski's rules broken 0
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Canonical SMILES Nc1cccc(c1)S(=O)(=O)N1CCCN(CC1)S(=O)(=O)c1ccc2c(c1)OCCO2
Isomeric SMILES Nc1cccc(c1)S(=O)(=O)N1CCCN(CC1)S(=O)(=O)c1ccc2c(c1)OCCO2
InChI InChI=1S/C19H23N3O6S2/c20-15-3-1-4-16(13-15)29(23,24)21-7-2-8-22(10-9-21)30(25,26)17-5-6-18-19(14-17)28-12-11-27-18/h1,3-6,13-14H,2,7-12,20H2
1. Anastasiou D, Yu Y, Israelsen WJ, Jiang JK, Boxer MB, Hong BS, Tempel W, Dimov S, Shen M, Jha A et al.. (2012)
Pyruvate kinase M2 activators promote tetramer formation and suppress tumorigenesis.
Nat Chem Biol, 8 (10): 839-47. [PMID:22922757]
2. Walsh MJ, Brimacombe KR, Veith H, Bougie JM, Daniel T, Leister W, Cantley LC, Israelsen WJ, Vander Heiden MG, Shen M et al.. (2011)
2-Oxo-N-aryl-1,2,3,4-tetrahydroquinoline-6-sulfonamides as activators of the tumor cell specific M2 isoform of pyruvate kinase.
Bioorg Med Chem Lett, 21 (21): 6322-7. [PMID:21958545]