Ligand (S)-naringenin

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Basic Ligand Information

Molecular Structure
Picture of (S)-naringenin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H12O5
(S)-naringenin
FTVWIRXFELQLPI-ZDUSSCGKSA-N
Synonyms:
(-)-(2S)-naringenin, (-)-naringenin, (2S)-5,7,4'-trihydroxyflavanone, (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, (2S)-naringenin, (S)-4',5,7-trihydroxyflavanone, 2S-naringenin, naringenin, S-naringenin

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin + [reduced NADPH-hemoprotein reductase] + O2 = 2-hydroxynaringenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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naringenin + [reduced NADPH-hemoprotein reductase] + O2 = apigenin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
naringenin + 2-oxoglutarate + O2 = kaempferol + succinate + CO2 + H2O
show the reaction diagram
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S-adenosyl-L-methionine + naringenin = S-adenosyl-L-homocysteine + ponciretin
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin-7-beta-glucopyranoside + H2O = naringenin + beta-D-glucose
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (71 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin + NADPH + H+ = apiferol + NADP+
show the reaction diagram
-
naringenin + [reduced NADPH-hemoprotein reductase] + O2 = eriodictyol + 6-hydroxyeriodictyol + 8-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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naringenin + [reduced NADPH-hemoprotein reductase] + O2 = apigenin + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
(2S)-naringenin + NADPH = ?
show the reaction diagram
-
S-adenosyl-L-methionine + naringenin = S-adenosyl-L-homocysteine + ponciretin
show the reaction diagram
-
S-adenosyl-L-methionine + (2S)-5,7,4'-trihydroxyflavanone = S-adenosyl-L-homocysteine + (2S)-5,4'-dihydroxy-7-methoxyflavanone
show the reaction diagram
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UDP-glucose + naringenin = UDP + naringenin 7-O-beta-D-glucoside
show the reaction diagram
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UDP-glucose + naringenin = UDP + naringenin 7-O-glucoside
show the reaction diagram
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UDP-glucose + naringenin = UDP + naringenin 7-O-beta-D-glucoside
show the reaction diagram
-
UDPglucose + naringenin = ?
show the reaction diagram
-
UDP-alpha-D-glucose + naringenin = ?
show the reaction diagram
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UDP-alpha-D-glucose + naringenin = UDP + naringenin-7-O-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + naringenin = UDP + ?
show the reaction diagram
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sucrose + naringenin = D-fructose + naringenin glucoside
show the reaction diagram
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dimethylallyl diphosphate + naringenin = diphosphate + 6-(3-methylbut-2-enyl)naringenin
show the reaction diagram
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3'-phosphoadenylylsulfate + naringenin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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naringenin + H2O = beta-D-glucose + naringenin
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
narirutin + H2O = naringenin + 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
very potent inhibitor, 0.02 mM inhibits by 71.9%
-
above 0.1 mM
-
0.010 mM, 50% inhibition, oxidation of androstandiol
-
IC50: 0.336 mM
-
non competitive with I-, competitive with H2O2
-
IC50: 0.25 mM
-
the content of naringenin in Mentha aquatica might explain its use in traditional medicine for depression-like conditions; the content of naringenin in Mentha aquatica might explain its use in traditional medicine for depression-like conditions
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naringenin docks more strongly with efKAS III than apigenin, resulting in the intensive hydrogen bond network between naringenin and efKAS III. Only naringenin shows antibacterial activity against Enterococcus faecalis at 0.256 mg/ml
-
1 mM: 72% inhibition, 0.1 mM: 54% inhibition
-
might inhibit the enzyme
-
; inhibition of SULT1A1; partial inhibition of SULT1A3; significantly inhibits the activity of SULT1A1
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a flavanone, 0.888 mM, pH 6.0, room temperature, 26.9% maximum inhibition
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mixed type, nearly noncompetitive inhibition
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slight inhibition
-
50% inhibition of rhGLO I at 0.1 mM
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lowest degree of inhibition, flavonoid in Helichrysum pamphylicum
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (13 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
10.6
-
pH 7.0, 25°C
25
-
pH 8.5, 30°C, purified recombinant GST-tagged NOMT
0.89
-
at pH 7.2 and 30°C
0.45
-
at pH 7.2 and 30°C
0.023
-
pH not specified in the publication, 37°C

KM Value (46 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.021
0.023
-
0.001
-
pH 7.0, 25°C
0.0087
-
pH 7.5, temperature not specified in the publication
0.0019
-
pH 8.5, 30°C, purified recombinant GST-tagged NOMT
0.073
-
pH 6.9, 25°C
0.0547
-
at pH 7.2 and 30°C
0.01
-
-
0.99
-
pH not specified in the publication, 37°C

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.00343
-
pH 6.9, temperature not specified in the publication
1137
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
1490
0.007
-
-
6216

IC50 Value (15 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00037
-
at pH 7.4 and 37°C
0.0215
-
pH 6.9, temperature not specified in the publication
0.0024
-
-
0.336
-
IC50: 0.336 mM
0.25
-
IC50: 0.25 mM
0.955
-
;
0.0079
-
25°C, pH 7.4, cell lysate
0.075
-
pH 6.8, 30°C
0.0732
-
at pH 2.0 and 37°C

References & Links

Links to other databases for (S)-naringenin

ChEBI
PubChem
ChEBI
PubChem