batrachotoxin   Click here for help

GtoPdb Ligand ID: 2619

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 7
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 104.25
Molecular weight 538.3
XLogP 1.5
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CN1CCOC23C(C1)(CC(O)C14C3=CCC3C4(C)CCC(O1)(O)C3)C(=CC2)C(OC(=O)c1c(C)c[nH]c1C)C
Isomeric SMILES CN1CCO[C@@]23[C@](C1)(C[C@@H](O)[C@]14C3=CC[C@H]3[C@]4(C)CC[C@](O1)(O)C3)C(=CC2)[C@@H](OC(=O)c1c(C)c[nH]c1C)C
InChI InChI=1S/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1
1. Bosmans F, Maertens C, Verdonck F, Tytgat J. (2004)
The poison Dart frog's batrachotoxin modulates Nav1.8.
FEBS Lett, 577 (1-2): 245-8. [PMID:15527793]
2. Linford NJ, Cantrell AR, Qu Y, Scheuer T, Catterall WA. (1998)
Interaction of batrachotoxin with the local anesthetic receptor site in transmembrane segment IVS6 of the voltage-gated sodium channel.
Proc Natl Acad Sci USA, 95 (23): 13947-52. [PMID:9811906]
3. Sheldon RS, Cannon NJ, Duff HJ. (1986)
Binding of [3H]batrachotoxinin A benzoate to specific sites on rat cardiac sodium channels.
Mol Pharmacol, 30 (6): 617-23. [PMID:2431264]
4. Wang SY, Wang GK. (1998)
Point mutations in segment I-S6 render voltage-gated Na+ channels resistant to batrachotoxin.
Proc Natl Acad Sci USA, 95 (5): 2653-8. [PMID:9482942]