(S)-N-[1-(3-morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide   Click here for help

GtoPdb Ligand ID: 2600

Synonyms: (S)-1 [PMID: 16904708] [1] | compound 2 [PMID: 12852750] [2]
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 41.57
Molecular weight 336.18
XLogP 3.86
No. Lipinski's rules broken 0
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Canonical SMILES O=C(NC(c1cccc(c1)N1CCOCC1)C)C=Cc1ccccc1
Isomeric SMILES O=C(N[C@H](c1cccc(c1)N1CCOCC1)C)/C=C/c1ccccc1
InChI InChI=1S/C21H24N2O2/c1-17(22-21(24)11-10-18-6-3-2-4-7-18)19-8-5-9-20(16-19)23-12-14-25-15-13-23/h2-11,16-17H,12-15H2,1H3,(H,22,24)/b11-10+/t17-/m0/s1
1. Bentzen BH, Schmitt N, Calloe K, Dalby Brown W, Grunnet M, Olesen SP. (2006)
The acrylamide (S)-1 differentially affects Kv7 (KCNQ) potassium channels.
Neuropharmacology, 51 (6): 1068-77. [PMID:16904708]
2. Wu YJ, Boissard CG, Greco C, Gribkoff VK, Harden DG, He H, L'Heureux A, Kang SH, Kinney GG, Knox RJ, Natale J, Newton AE, Lehtinen-Oboma S, Sinz MW, Sivarao DV, Starrett JE, Sun LQ, Tertyshnikova S, Thompson MW, Weaver D, Wong HS, Zhang L, Dworetzky SI. (2003)
(S)-N-[1-(3-morpholin-4-ylphenyl)ethyl]- 3-phenylacrylamide: an orally bioavailable KCNQ2 opener with significant activity in a cortical spreading depression model of migraine.
J Med Chem, 46 (15): 3197-200. [PMID:12852750]