K-252a   

GtoPdb Ligand ID: 336

Synonyms: K252a | ST50826373 | staurosporine aglycone
Comment: K252a is an alkaloid isolated from Nocardiopisis soil fungi. It is an analogue of staurosporine. There is some ambiguity surrounding the exact stereochemistry of this compound, with an alternative representation being CID 3035817.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 94.72
Molecular weight 467.15
XLogP 5.34
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C1(O)CC2OC1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
Isomeric SMILES COC(=O)[C@]1(O)C[C@@H]2O[C@@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
InChI InChI=1S/C27H21N3O5/c1-26-27(33,25(32)34-2)11-18(35-26)29-16-9-5-3-7-13(16)20-21-15(12-28-24(21)31)19-14-8-4-6-10-17(14)30(26)23(19)22(20)29/h3-10,18,33H,11-12H2,1-2H3,(H,28,31)/t18-,26+,27+/m0/s1
InChI Key KOZFSFOOLUUIGY-IYYJOCMQSA-N
References
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. 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]
3. Hashimoto Y, Nakayama T, Teramoto T, Kato H, Watanabe T, Kinoshita M, Tsukamoto K, Tokunaga K, Kurokawa K, Nakanishi S. (1991)
Potent and preferential inhibition of Ca2+/calmodulin-dependent protein kinase II by K252a and its derivative, KT5926.
Biochem. Biophys. Res. Commun., 181 (1): 423-9. [PMID:1659814]
4. Lazareno S, Popham A, Birdsall NJ. (2000)
Allosteric interactions of staurosporine and other indolocarbazoles with N-[methyl-(3)H]scopolamine and acetylcholine at muscarinic receptor subtypes: identification of a second allosteric site.
Mol. Pharmacol., 58 (1): 194-207. [PMID:10860942]