compound 16 [PMID: 31977207]   Click here for help

GtoPdb Ligand ID: 10650

Compound class: Synthetic organic
Comment: Compound 16 (acidified with fumaric acid) is reported as an activator of pyruvate kinase M2 (PKM2) that has in vivo anti-tumour activity against glioblastoma multiforme xenografts [1]. It is a prodrug, with the active form being compound 5 in the discovery article.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 0
Rotatable bonds 14
Topological polar surface area 145.97
Molecular weight 716.39
XLogP 1.45
No. Lipinski's rules broken 2
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Canonical SMILES CN(CC1C(=O)O[C@H]2[C@H]1CC/C(=C\CC[C@@]1([C@H]2O1)C)/C(=O)OCCOCCOC(=O)/C/1=C/CC[C@@]2(C)O[C@H]2[C@@H]2[C@@H](CC1)[C@H](CN(C)C)C(=O)O2)C
Isomeric SMILES CN(CC1C(=O)O[C@H]2[C@H]1CC/C(=C\CC[C@@]1([C@H]2O1)C)/C(=O)OCCOCCOC(=O)/C/1=C/CC[C@@]2(C)O[C@H]2[C@@H]2[C@@H](CC1)[C@H](CN(C)C)C(=O)O2)C
InChI InChI=1S/C38H56N2O11/c1-37-15-7-9-23(11-13-25-27(21-39(3)4)35(43)48-29(25)31(37)50-37)33(41)46-19-17-45-18-20-47-34(42)24-10-8-16-38(2)32(51-38)30-26(14-12-24)28(22-40(5)6)36(44)49-30/h9-10,25-32H,7-8,11-22H2,1-6H3/b23-9+,24-10+/t25-,26-,27-,28?,29-,30-,31-,32-,37+,38+/m0/s1
1. Ding Y, Xue Q, Liu S, Hu K, Wang D, Wang T, Li Y, Guo H, Hao X, Ge W et al.. (2020)
Identification of Parthenolide Dimers as Activators of Pyruvate Kinase M2 in Xenografts of Glioblastoma Multiforme in Vivo.
J Med Chem, 63 (4): 1597-1611. [PMID:31977207]