(-)-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].
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2D Structure
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Physico-chemical Properties
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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
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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
1. Akbulut Y, Gaunt HJ, Muraki K, Ludlow MJ, Amer MS, Bruns A, Vasudev NS, Radtke L, Willot M, Hahn S et al.. (2015)
(-)-Englerin A is a potent and selective activator of TRPC4 and TRPC5 calcium channels.
Angew Chem Int Ed Engl, 54 (12): 3787-91. [PMID:25707820]
2. Molawi K, Delpont N, Echavarren AM. (2010)
Enantioselective synthesis of (-)-englerins A and B.
Angew Chem Int Ed Engl, 49 (20): 3517-9. [PMID:20544903]
3. Radtke L, Willot M, Sun H, Ziegler S, Sauerland S, Strohmann C, Fröhlich R, Habenberger P, Waldmann H, Christmann M. (2011)
Total synthesis and biological evaluation of (-)-englerin A and B: synthesis of analogues with improved activity profile.
Angew Chem Int Ed Engl, 50 (17): 3998-4002. [PMID:21472928]
4. Ratnayake R, Covell D, Ransom TT, Gustafson KR, Beutler JA. (2009)
Englerin A, a selective inhibitor of renal cancer cell growth, from Phyllanthus engleri.
Org Lett, 11 (1): 57-60. [PMID:19061394]
5. Zhou Q, Chen X, Ma D. (2010)
Asymmetric, protecting-group-free total synthesis of (-)-englerin A.
Angew Chem Int Ed Engl, 49 (20): 3513-6. [PMID:20544902]