brucine   Click here for help

GtoPdb Ligand ID: 342

Synonyms: 10,11-dimethoxy strychnine
Comment: Brucine is a bitter alkaloid toxin, closely related to strychnine. It produces paralysis of sensory nerves and peripheral motor nerves.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 51.24
Molecular weight 394.19
XLogP 0.13
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc2c(cc1OC)N1C3C42CCN2C4CC4C3C(CC1=O)OCC=C4C2
Isomeric SMILES COc1cc2c(cc1OC)N1[C@@H]3[C@@]42CCN2[C@H]4C[C@@H]4[C@H]3[C@H](CC1=O)OCC=C4C2
InChI InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
1. Birdsall NJ, Farries T, Gharagozloo P, Kobayashi S, Lazareno S, Sugimoto M. (1999)
Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies.
Mol Pharmacol, 55 (4): 778-86. [PMID:10101037]
2. Jakubík J, Bacáková L, El-Fakahany EE, Tucek S. (1997)
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.
Mol Pharmacol, 52 (1): 172-9. [PMID:9224827]
3. Lazareno S, Gharagozloo P, Kuonen D, Popham A, Birdsall NJ. (1998)
Subtype-selective positive cooperative interactions between brucine analogues and acetylcholine at muscarinic receptors: radioligand binding studies.
Mol Pharmacol, 53 (3): 573-89. [PMID:9495826]