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 386.12130
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-(trans-sinapoyl)-β-D-glucose UniProt
1-O-[(2E)-sinapoyl]-β-D-glucopyranose ChEBI
1-O-[(2E)-sinapoyl]-β-D-glucose ChEBI
1-O-[(E)-sinapoyl]-β-D-glucopyranose ChEBI
1-O-Sinapoyl beta-D-glucoside KEGG COMPOUND
1-O-Sinapoyl beta-D-glucoside KEGG COMPOUND
1-O-Sinapoyl-beta-D-glucose KEGG COMPOUND
Manual Xrefs Databases
C00013592 KNApSAcK
C01175 KEGG COMPOUND
SGS PDBeChem
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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
09 August 2019