aconitine   

GtoPdb Ligand ID: 2617

Comment: This compound is also represented on ChEMBL by the entry CHEMBL2103747 which has slightly diffferent stereochemistry than the structure shown here.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 153.45
Molecular weight 645.31
XLogP 0.49
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES COCC12CN(CC)C3C4(C2C(OC)C3C2(C3C4CC(C3OC(=O)c3ccccc3)(C(C2O)OC)O)OC(=O)C)C(CC1O)OC
Isomeric SMILES COC[C@@]12CN(CC)C3[C@]4([C@@H]2[C@@H](OC)[C@@H]3[C@@]2([C@@H]3[C@H]4C[C@@]([C@@H]3OC(=O)c3ccccc3)([C@H]([C@@H]2O)OC)O)OC(=O)C)[C@H](C[C@H]1O)OC
InChI InChI=1S/C34H47NO11/c1-7-35-15-31(16-41-3)20(37)13-21(42-4)33-19-14-32(40)28(45-30(39)18-11-9-8-10-12-18)22(19)34(46-17(2)36,27(38)29(32)44-6)23(26(33)35)24(43-5)25(31)33/h8-12,19-29,37-38,40H,7,13-16H2,1-6H3/t19-,20-,21+,22-,23+,24+,25-,26?,27+,28-,29+,31+,32-,33+,34-/m1/s1
InChI Key XFSBVAOIAHNAPC-XTHSEXKGSA-N
References
1. Catterall WA, Morrow CS, Daly JW, Brown GB. (1981)
Binding of batrachotoxinin A 20-alpha-benzoate to a receptor site associated with sodium channels in synaptic nerve ending particles.
J. Biol. Chem., 256 (17): 8922-7. [PMID:6114956]
2. Nilius B, Boldt W, Benndorf K. (1986)
Properties of aconitine-modified sodium channels in single cells of mouse ventricular myocardium.
Gen. Physiol. Biophys., 5 (5): 473-84. [PMID:2433183]
3. Wright SN. (2002)
Comparison of aconitine-modified human heart (hH1) and rat skeletal (mu1) muscle Na+ channels: an important role for external Na+ ions.
J. Physiol. (Lond.), 538 (Pt 3): 759-71. [PMID:11826163]