compound 31 [PMID: 22902653]   Click here for help

GtoPdb Ligand ID: 8117

Compound class: Synthetic organic
Comment: Compound 31 was designed as an inhibitor of the LIM domain kinases LIMK1 and LIMK2 [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 143.05
Molecular weight 461.16
XLogP 1.7
No. Lipinski's rules broken 0
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Canonical SMILES CCNC(=O)Nc1ncc(s1)c1cc(nc(n1)c1cnccn1)c1c(C)cc(cc1C)OC
Isomeric SMILES CCNC(=O)Nc1ncc(s1)c1cc(nc(n1)c1cnccn1)c1c(C)cc(cc1C)OC
InChI InChI=1S/C23H23N7O2S/c1-5-25-22(31)30-23-27-12-19(33-23)16-10-17(20-13(2)8-15(32-4)9-14(20)3)29-21(28-16)18-11-24-6-7-26-18/h6-12H,5H2,1-4H3,(H2,25,27,30,31)
1. Arber S, Barbayannis FA, Hanser H, Schneider C, Stanyon CA, Bernard O, Caroni P. (1998)
Regulation of actin dynamics through phosphorylation of cofilin by LIM-kinase.
Nature, 393 (6687): 805-9. [PMID:9655397]
2. He L, Seitz SP, Trainor GL, Tortolani D, Vaccaro W, Poss M, Tarby CM, Tokarski JS, Penhallow B, Hung CY et al.. (2012)
Modulation of cofilin phosphorylation by inhibition of the Lim family kinases.
Bioorg Med Chem Lett, 22 (18): 5995-8. [PMID:22902653]
3. Johne C, Matenia D, Li XY, Timm T, Balusamy K, Mandelkow EM. (2008)
Spred1 and TESK1--two new interaction partners of the kinase MARKK/TAO1 that link the microtubule and actin cytoskeleton.
Mol Biol Cell, 19 (4): 1391-403. [PMID:18216281]
4. Røsok O, Pedeutour F, Ree AH, Aasheim HC. (1999)
Identification and characterization of TESK2, a novel member of the LIMK/TESK family of protein kinases, predominantly expressed in testis.
Genomics, 61 (1): 44-54. [PMID:10512679]
5. Toshima J, Toshima JY, Takeuchi K, Mori R, Mizuno K. (2001)
Cofilin phosphorylation and actin reorganization activities of testicular protein kinase 2 and its predominant expression in testicular Sertoli cells.
J Biol Chem, 276 (33): 31449-58. [PMID:11418599]
6. Yang N, Higuchi O, Ohashi K, Nagata K, Wada A, Kangawa K, Nishida E, Mizuno K. (1998)
Cofilin phosphorylation by LIM-kinase 1 and its role in Rac-mediated actin reorganization.
Nature, 393 (6687): 809-12. [PMID:9655398]