chelerythrine   Click here for help

GtoPdb Ligand ID: 5953

Synonyms: broussonpapyrine | cheleritrine | chelerythrine hydroxide | toddalin
PDB Ligand
Comment: Chelerythrine is a potent, selective, and cell-permeable protein kinase C inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 0
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 40.8
Molecular weight 348.12
XLogP 5.62
No. Lipinski's rules broken 1
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Canonical SMILES COc1c(OC)ccc2c1c[n+](C)c1c2ccc2c1cc1OCOc1c2
Isomeric SMILES COc1c(OC)ccc2c1c[n+](C)c1c2ccc2c1cc1OCOc1c2
InChI InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1039-45. [PMID:22037377]
2. Fedorov O, Marsden B, Pogacic V, Rellos P, Müller S, Bullock AN, Schwaller J, Sundström M, Knapp S. (2007)
A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases.
Proc Natl Acad Sci USA, 104 (51): 20523-8. [PMID:18077363]
3. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem J, 451 (2): 313-28. [PMID:23398362]
4. Shemon AN, Sluyter R, Conigrave AD, Wiley JS. (2004)
Chelerythrine and other benzophenanthridine alkaloids block the human P2X7 receptor.
Br J Pharmacol, 142 (6): 1015-9. [PMID:15210579]