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
SMILES / InChI / InChIKey
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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
InChI Key XYUFCXJZFZPEJD-XMSQKQJNSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
2-[2,6-dihydroxy-4-[(3R,4R)-3-[(4-hydroxybenzoyl)amino]azepan-4-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid
Synonyms Click here for help
azepinostatin
Database Links Click here for help
CAS Registry No. 63590-19-2
ChEMBL Ligand CHEMBL60254
DrugBank Ligand DB04098
GtoPdb PubChem SID 249565822
PubChem CID 5287736
RCSB PDB Ligand BA1
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SynPHARM 81500 (in complex with beta adrenergic receptor kinase 1)
Wikipedia Balanol