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ChEBI
> Main
CHEBI:28327 - naringenin 7-
O
-β-
D
-glucoside
Main
ChEBI Ontology
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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
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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
(2
S
)-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
(2
S
)-
5-
hydroxy-
2-
(4-
hydroxyphenyl)-
4-
oxo-
3,4-
dihydro-
2
H
-
chromen-
7-
yl β-
D
-
glucopyranoside
Synonyms
Sources
(2
S
)-naringenin 7-
O
-β-
D
-glucoside
UniProt
(
S
)-
7-
(β-
D
-
glucopyranosyloxy)-
2,3-
dihydro-
5-
hydroxy-
2-
(4-
hydroxyphenyl)-
4
H
-
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