CHEBI:16546 - 1-O-sinapoyl-β-D-glucose

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 1-O-sinapoyl-β-D-glucose
ChEBI ID CHEBI:16546
ChEBI ASCII Name 1-O-sinapoyl-beta-D-glucose
Definition A glucosyl hydroxycinnamic acid that is the cinnamate ester obtained by the formal condensation of the carboxy group of trans-sinapic acid with the anomeric hydroxy group of β-D-glucose.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:657, CHEBI:45550, CHEBI:658, CHEBI:11219, CHEBI:18986, CHEBI:11218
Supplier Information
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Formula C17H22O10
Net Charge 0
Average Mass 386.35058
Monoisotopic Mass 386.121
InChI InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
InChIKey XRKBRPFTFKKHEF-DGDBGZAXSA-N
SMILES COc1cc(cc(OC)c1O)\C=C\C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 1-O-sinapoyl-β-D-glucose (CHEBI:16546) has functional parent β-D-glucose (CHEBI:15903)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) has functional parent trans-sinapic acid (CHEBI:15714)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) has role plant metabolite (CHEBI:76924)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) is a cinnamate ester (CHEBI:36087)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) is a dimethoxybenzene (CHEBI:51681)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) is a glucosyl hydroxycinnamic acid (CHEBI:24282)
1-O-sinapoyl-β-D-glucose (CHEBI:16546) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name
(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl β-D-glucopyranoside
Synonyms Sources
(E)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)-2H-PYRAN-2-YL 3-(4-HYDROXY-3,5-DIMETHOXYPHENYL)ACRYLATE PDBeChem
1-O-Sinapoyl beta-D-glucoside KEGG COMPOUND
1-O-Sinapoyl beta-D-glucoside KEGG COMPOUND
1-O-Sinapoyl-beta-D-glucose KEGG COMPOUND
1-O-sinapoyl-β-D-glucose UniProt
Database Links Databases
C00013592 KNApSAcK
C01175 KEGG COMPOUND
SGS PDBeChem
View more database links
Registry Number Type Source
4272186 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24241853 PubMed citation Europe PMC
24271623 PubMed citation Europe PMC
Last Modified
28 July 2014