compound 34 [PMID: 24749861]   Click here for help

GtoPdb Ligand ID: 8129

Compound class: Synthetic organic
Comment: Compound 34 is a potent inhibitor of the protein kinase ERN1 (endoplasmic reticulum to nucleus signaling 1) [1]. ERN1 is also known as IRE1, and is an endoplasmic reticulum stress sensor which signals to the nucleus in response to abnormal levels of unfolded proteins. Compound 34 inhibits the RNAse domain of the protein, like other salicylaldehyde-containing molecules.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 120.62
Molecular weight 287.09
XLogP 2.4
No. Lipinski's rules broken 0
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Canonical SMILES O=Cc1c(O)ccc2c1oc(=O)c1c2CCN(C1)C(=N)N
Isomeric SMILES O=Cc1c(O)ccc2c1oc(=O)c1c2CCN(C1)C(=N)N
InChI InChI=1S/C14H13N3O4/c15-14(16)17-4-3-7-8-1-2-11(19)10(6-18)12(8)21-13(20)9(7)5-17/h1-2,6,19H,3-5H2,(H3,15,16)
1. Ranatunga S, Tang CH, Kang CW, Kriss CL, Kloppenburg BJ, Hu CC, Del Valle JR. (2014)
Synthesis of novel tricyclic chromenone-based inhibitors of IRE-1 RNase activity.
J. Med. Chem., 57 (10): 4289-301. [PMID:24749861]