(-)-englerin A   Click here for help

GtoPdb Ligand ID: 8372

Compound class: Synthetic organic
Comment: (-)-englerin A is a plant extract from the bark of Phyllanthus engleri [4]. (-)-englerin A is a potent and selective agonist of TRPC4 and TRPC5 calcium channels [1] with cytotoxic activity selective for several renal cancer cell lines [4]. The (+) enantiomer is inactive against the same cells [3]. The compound has been chemically synthesised [2-3,5].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 82.06
Molecular weight 442.24
XLogP 4.66
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC(=O)OC1CC2(OC1(C)C1CCC(C1C2OC(=O)C=Cc1ccccc1)C)C(C)C
Isomeric SMILES OCC(=O)O[C@@H]1C[C@@]2(O[C@@]1(C)[C@@H]1CC[C@H]([C@H]1[C@@H]2OC(=O)/C=C/c1ccccc1)C)C(C)C
InChI InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1
Bioactivity Comments
Englerin A is reported to selectively inhibit renal cancer cell growth [4] in vitro with a reported IC50 of 45nM against A498 kidney cancer cells [3].
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPC5 Primary target of this compound Hs Activator Agonist 8.1 pEC50 - 1
pEC50 8.1 [1]
TRPC4 Primary target of this compound Hs Activator Agonist 7.9 pEC50 - 1
pEC50 7.9 [1]