brucine   

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.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key RRKTZKIUPZVBMF-IBTVXLQLSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(1R,11S,18S,20R,21R,22S)-4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2(7),3,5,14-tetraen-9-one
Synonyms
10,11-dimethoxy strychnine
Database Links
CAS Registry No. 357-57-3 (source: Scifinder)
ChEBI CHEBI:3193
ChEMBL Ligand CHEMBL501756
GtoPdb PubChem SID 135652672
PubChem CID 442021
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Wikipedia Brucine