CHEBI:28327 - naringenin 7-O-β-D-glucoside

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name naringenin 7-O-β-D-glucoside
ChEBI ID CHEBI:28327
ChEBI ASCII Name naringenin 7-O-beta-D-glucoside
Definition A flavanone 7-O-β-D-glucoside that is (S)-naringenin substituted by a β-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:25485, CHEBI:7484
Supplier Information ChemicalBook:CB6112967, ChemicalBook:CB32551563, eMolecules:479469, ZINC000001530575
Download Molfile XML SDF
Formula C21H22O10
Net Charge 0
Average Mass 434.39338
Monoisotopic Mass 434.12130
InChI InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1
InChIKey DLIKSSGEMUFQOK-SFTVRKLSSA-N
SMILES OC[C@H]1O[C@@H](Oc2cc(O)c3C(=O)C[C@H](Oc3c2)c2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
antilipemic drug
A substance used to treat hyperlipidemia (an excess of lipids in the blood).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing naringenin 7-O-β-D-glucoside (CHEBI:28327) has functional parent (S)-naringenin (CHEBI:17846)
naringenin 7-O-β-D-glucoside (CHEBI:28327) has role antibacterial agent (CHEBI:33282)
naringenin 7-O-β-D-glucoside (CHEBI:28327) has role antilipemic drug (CHEBI:35679)
naringenin 7-O-β-D-glucoside (CHEBI:28327) has role hypoglycemic agent (CHEBI:35526)
naringenin 7-O-β-D-glucoside (CHEBI:28327) has role metabolite (CHEBI:25212)
naringenin 7-O-β-D-glucoside (CHEBI:28327) is a (2S)-flavan-4-one (CHEBI:140377)
naringenin 7-O-β-D-glucoside (CHEBI:28327) is a 4'-hydroxyflavanones (CHEBI:140331)
naringenin 7-O-β-D-glucoside (CHEBI:28327) is a dihydroxyflavanone (CHEBI:38749)
naringenin 7-O-β-D-glucoside (CHEBI:28327) is a flavanone 7-O-β-D-glucoside (CHEBI:13637)
naringenin 7-O-β-D-glucoside (CHEBI:28327) is a monosaccharide derivative (CHEBI:63367)
IUPAC Name
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside
Synonyms Sources
(2S)-naringenin 7-O-β-D-glucoside UniProt
(S)-7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ChemIDplus
Naringenin 7-O-beta-D-glucoside KEGG COMPOUND
Prunin KEGG COMPOUND
Manual Xrefs Databases
C00000998 KNApSAcK
C09099 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
529-55-5 CAS Registry Number KEGG COMPOUND
529-55-5 CAS Registry Number ChemIDplus
66743 Reaxys Registry Number Reaxys
Citations Types Sources
1896517 PubMed citation Europe PMC
20553344 PubMed citation Europe PMC
21941631 PubMed citation Europe PMC
23202537 PubMed citation Europe PMC
23354392 PubMed citation Europe PMC
Last Modified
19 August 2020