balanol   Click here for help

GtoPdb Ligand ID: 8142

Synonyms: azepinostatin
PDB Ligand
Comment: Balanol is a fungal metabolite which acts as a non-selective ATP-competitive inhibitor of protein kinases A, G and C (AGC family kinases) [1-3]. Balanol is also reported to inhibit G protein-coupled receptor kinases (GRKs), with modest selectivity for the GRK2 family members, GRK2 and GRK3 [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 7
Rotatable bonds 9
Topological polar surface area 202.72
Molecular weight 550.16
XLogP 4.2
No. Lipinski's rules broken 1
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Canonical SMILES Oc1ccc(cc1)C(=O)NC1CNCCCC1OC(=O)c1cc(O)c(c(c1)O)C(=O)c1c(O)cccc1C(=O)O
Isomeric SMILES Oc1ccc(cc1)C(=O)N[C@@H]1CNCCC[C@H]1OC(=O)c1cc(O)c(c(c1)O)C(=O)c1c(O)cccc1C(=O)O
InChI InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1
1. Defauw JM, Murphy MM, Jagdmann Jr GE, Hu H, Lampe JW, Hollinshead SP, Mitchell TJ, Crane HM, Heerding JM, Mendoza JS et al.. (1996)
Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A.
J Med Chem, 39 (26): 5215-27. [PMID:8978850]
2. Koide K, Bunnage ME, Gomez Paloma L, Kanter JR, Taylor SS, Brunton LL, Nicolaou KC. (1995)
Molecular design and biological activity of potent and selective protein kinase inhibitors related to balanol.
Chem Biol, 2 (9): 601-8. [PMID:9383464]
3. Ohshima S, Yanagisawa M, Katoh A, Fujii T, Sano T, Matsukuma S, Furumai T, Fujiu M, Watanabe K, Yokose K et al.. (1994)
Fusarium merismoides Corda NR 6356, the source of the protein kinase C inhibitor, azepinostatin. Taxonomy, yield improvement, fermentation and biological activity.
J Antibiot, 47 (6): 639-47. [PMID:8040068]
4. Tesmer JJ, Tesmer VM, Lodowski DT, Steinhagen H, Huber J. (2010)
Structure of human G protein-coupled receptor kinase 2 in complex with the kinase inhibitor balanol.
J Med Chem, 53 (4): 1867-70. [PMID:20128603]