CHEBI:16353 - sinapine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name sinapine
ChEBI ID CHEBI:16353
Definition An acylcholine in which the acyl group specified is sinapoyl.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:9156, CHEBI:15088, CHEBI:26682, CHEBI:26687
Supplier Information ChemicalBook:CB41073797, ZINC000001532786
Download Molfile XML SDF
Formula C16H24NO5
Net Charge +1
Average Mass 310.36550
Monoisotopic Mass 310.16490
InChI InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
InChIKey HUJXHFRXWWGYQH-UHFFFAOYSA-O
SMILES COc1cc(cc(OC)c1O)\C=C\C(=O)OCC[N+](C)(C)C
Metabolite of Species Details
Brassica napus (NCBI:txid3708) See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
photosynthetic electron-transport chain inhibitor

Application(s): photosynthetic electron-transport chain inhibitor

View more via ChEBI Ontology
ChEBI Ontology
Outgoing sinapine (CHEBI:16353) has functional parent trans-sinapic acid (CHEBI:15714)
sinapine (CHEBI:16353) has role antioxidant (CHEBI:22586)
sinapine (CHEBI:16353) has role photosynthetic electron-transport chain inhibitor (CHEBI:26087)
sinapine (CHEBI:16353) has role plant metabolite (CHEBI:76924)
sinapine (CHEBI:16353) is a acylcholine (CHEBI:35287)
IUPAC Name
2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyloxy]-N,N,N-trimethylethanaminium
Synonyms Sources
2-(4-hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium ChEBI
O-sinapoylcholine ChEBI
O-sinapoylcholine UniProt
Sinapine KEGG COMPOUND
Sinapoylcholine KEGG COMPOUND
Sinapoylcholine KEGG COMPOUND
Manual Xrefs Databases
C00002777 KNApSAcK
C00933 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
18696-26-9 CAS Registry Number KEGG COMPOUND
18696-26-9 CAS Registry Number ChemIDplus
4933491 Reaxys Registry Number Reaxys
Citations
Fang J, Reichelt M, Kai M, Schneider B (2012)
Metabolic profiling of lignans and other secondary metabolites from rapeseed ( Brassica napus L.).
Journal of agricultural and food chemistry 60, 10523-10529 [PubMed:23030806]
[show Abstract]
He L, Li HT, Guo SW, Liu LF, Qiu JB, Li F, Cai BC (2008)
[Inhibitory effects of sinapine on activity of acetylcholinesterase in cerebral homogenate and blood serum of rats].
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 33, 813-815 [PubMed:18589789]
[show Abstract]
Liu L, Wang Y, Li H, Ji Y (2006)
[Study of distribution of sinapine in commonly used crude drugs from cruciferous plants].
Se pu = Chinese journal of chromatography 24, 49-51 [PubMed:16827311]
[show Abstract]
Last Modified
04 May 2015