enzastaurin   Click here for help

GtoPdb Ligand ID: 5693

Synonyms: LY-317615 | LY317615
Compound class: Synthetic organic
Comment: Enzastaurin is a selective inhibitor of protein kinase Cβ [2-3]. Note that reported affinity values may have been generated using the hydrochloride salt (PubChem CID 176166).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 72.16
Molecular weight 515.23
XLogP 4.73
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1NC(=O)C(=C1c1cn(c2c1cccc2)C1CCN(CC1)Cc1ccccn1)c1cn(c2c1cccc2)C
Isomeric SMILES O=C1NC(=O)C(=C1c1cn(c2c1cccc2)C1CCN(CC1)Cc1ccccn1)c1cn(c2c1cccc2)C
InChI InChI=1S/C32H29N5O2/c1-35-19-25(23-9-2-4-11-27(23)35)29-30(32(39)34-31(29)38)26-20-37(28-12-5-3-10-24(26)28)22-13-16-36(17-14-22)18-21-8-6-7-15-33-21/h2-12,15,19-20,22H,13-14,16-18H2,1H3,(H,34,38,39)
InChI Key AXRCEOKUDYDWLF-UHFFFAOYSA-N
References
1. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM, Pallares G, Hocker M, Treiber DK, Zarrinkar PP. (2011)
Comprehensive analysis of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1046-51. [PMID:22037378]
2. Faul MM, Gillig JR, Jirousek MR, Ballas LM, Schotten T, Kahl A, Mohr M. (2003)
Acyclic N-(azacycloalkyl)bisindolylmaleimides: isozyme selective inhibitors of PKCbeta.
Bioorg. Med. Chem. Lett., 13 (11): 1857-9. [PMID:12749884]
3. Graff JR, McNulty AM, Hanna KR, Konicek BW, Lynch RL, Bailey SN, Banks C, Capen A, Goode R, Lewis JE et al.. (2005)
The protein kinase Cbeta-selective inhibitor, Enzastaurin (LY317615.HCl), suppresses signaling through the AKT pathway, induces apoptosis, and suppresses growth of human colon cancer and glioblastoma xenografts.
Cancer Res., 65 (16): 7462-9. [PMID:16103100]
4. Teicher BA, Alvarez E, Menon K, Esterman MA, Considine E, Shih C, Faul MM. (2002)
Antiangiogenic effects of a protein kinase Cbeta-selective small molecule.
Cancer Chemother. Pharmacol., 49 (1): 69-77. [PMID:11855754]
5. Wodicka LM, Ciceri P, Davis MI, Hunt JP, Floyd M, Salerno S, Hua XH, Ford JM, Armstrong RC, Zarrinkar PP et al.. (2010)
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
Chem. Biol., 17 (11): 1241-9. [PMID:21095574]