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BRENDA support

Ligand naringin

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Basic Ligand Information

Molecular Structure
Picture of naringin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C27H32O14
naringin
DFPMSGMNTNDNHN-ZPHOTFPESA-N
Synonyms:
naringenin 7-O-neohesperidoside, naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside], naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-L-rhamnose + naringenin 7-O-glucoside = UDP + naringenin 7-O-[beta-L-rhamnosyl-(1-2)-beta-D-glucoside]
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringin + NADH + H+ + O2 = eryodictyol + NADP+ + H2O
show the reaction diagram
-
malonyl-CoA + naringenin 7-O-neohesperidoside = ?
show the reaction diagram
-
naringin + maltodextrin = ?
show the reaction diagram
-
naringin + H2O = ?
show the reaction diagram
-
naringin + H2O = naringenin + rutinose
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 2.373 mM
-
about 15% inhibition at 0.045 mM
-
selective inhibitor, uncompetitive inhibition with respect to the substrate coniferyl aldehyde
-
weak, 0.1 mM, 12% inhibition
-
about 17% inhibition at 0.01 mM
-
inhibits enzyme phosphorylation
-
inhibition of SULT1A3
-
the enzymatic activity of native secretory phospholipase A2 is virtually abolished by treatment with naringin
-
13.7% inhibition at 1 mM
-
inhibition of the ACE2 enzyme
-
slight inhibition
-
i.e. 7-[[2-O-(6-deoxy-alpha-L-mannopyra nosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzo pyran-4-one. Pre-treatment with naringin prior to doxorubicin treatment increases the sensitivity of the enzyme to doxorubicin, naringin inhibits the doxorubicin-stimulated ATPase activity and may interact directly with the transporter. Naringin seems to modulate the in vivo expression of P-gp
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
27.7
-
pH 5.5, 95°C

KM Value (11 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.7
-
pH 5.5, 95°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.6
-
at pH 8.0 and 40°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2.373
-
IC50: 2.373 mM

References & Links

Links to other databases for naringin

ChEBI
PubChem
ChEBI
PubChem