GtoPdb Ligand ID: 2313

Compound class: Synthetic organic
Comment: While the INN-assigned preparation of dequalinium is in complex with chloride, the compound is also available experimentally as the 'parent' salt form. Two of the references listed here [1,4] refer to the parent compound, while [5] and [6] refer to dequalinium chloride. We show the structure of the parent compound, and our external links are also to this structure.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 59.8
Molecular weight 456.33
XLogP 9.69
No. Lipinski's rules broken 2
Canonical SMILES Nc1cc(C)[n+](c2c1cccc2)CCCCCCCCCC[n+]1c(C)cc(c2c1cccc2)N
Isomeric SMILES Nc1cc(C)[n+](c2c1cccc2)CCCCCCCCCC[n+]1c(C)cc(c2c1cccc2)N
InChI InChI=1S/C30H38N4/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3/p+2
1. Dreixler JC, Bian J, Cao Y, Roberts MT, Roizen JD, Houamed KM. (2000)
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
Eur. J. Pharmacol., 401 (1): 1-7. [PMID:10915830]
2. Rosenbaum T, Gordon-Shaag A, Islas LD, Cooper J, Munari M, Gordon SE. (2004)
State-dependent block of CNG channels by dequalinium.
J. Gen. Physiol., 123 (3): 295-304. [PMID:14981138]
3. Rosenbaum T, Islas LD, Carlson AE, Gordon SE. (2003)
Dequalinium: a novel, high-affinity blocker of CNGA1 channels.
J. Gen. Physiol., 121 (1): 37-47. [PMID:12508052]
4. Shah M, Haylett DG. (2000)
The pharmacology of hSK1 Ca2+-activated K+ channels expressed in mammalian cell lines.
Br. J. Pharmacol., 129 (4): 627-30. [PMID:10683185]
5. Strøbaek D, Jørgensen TD, Christophersen P, Ahring PK, Olesen SP. (2000)
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
Br. J. Pharmacol., 129 (5): 991-9. [PMID:10696100]
6. Terstappen GC, Pula G, Carignani C, Chen MX, Roncarati R. (2001)
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.
Neuropharmacology, 40 (6): 772-83. [PMID:11369031]