brucine   Click here for help

GtoPdb Ligand ID: 342

Synonyms: 10,11-dimethoxy strychnine
Compound class: Natural product
Comment: Brucine is a bitter alkaloid toxin, closely related to strychnine. It produces paralysis of sensory nerves and peripheral motor nerves.
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 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
Click here for help
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 Click here for help
Compound class Natural product
IUPAC Name Click here for help
(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 Click here for help
10,11-dimethoxy strychnine
Database Links Click here for help
Specialist databases
GPCRdb Ligand brucine
Other databases
CAS Registry No. 357-57-3 (source: Scifinder)
ChEBI CHEBI:3193
ChEMBL Ligand CHEMBL501756
GtoPdb PubChem SID 135652672
PubChem CID 442021
Search Google for chemical match using the InChIKey RRKTZKIUPZVBMF-IBTVXLQLSA-N
Search Google for chemicals with the same backbone RRKTZKIUPZVBMF
UniChem Compound Search for chemical match using the InChIKey RRKTZKIUPZVBMF-IBTVXLQLSA-N
UniChem Connectivity Search for chemical match using the InChIKey RRKTZKIUPZVBMF-IBTVXLQLSA-N
Wikipedia Brucine