Ligand naringenin

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Basic Ligand Information

Molecular Structure
Picture of naringenin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H12O5
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, (S)-naringenin, 2S-naringenin, S-naringenin
Pathway Source
Pathways
KEGG
Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Flavonoid biosynthesis, Isoflavonoid biosynthesis
MetaCyc
apigeninidin 5-O-glucoside biosynthesis, flavonoid biosynthesis, flavonoid biosynthesis (in equisetum), flavonoid di-C-glucosylation, isoflavonoid biosynthesis II more

Roles as Enzyme Ligand

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

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

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin-7-beta-glucopyranoside + H2O = naringenin + beta-D-glucose
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Substrate in Enzyme-catalyzed Reactions (78 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
naringenin + NADPH + H+ = apiferol + NADP+
show the reaction diagram
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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
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(2S)-naringenin + NADPH = ?
show the reaction diagram
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S-adenosyl-L-methionine + naringenin = S-adenosyl-L-homocysteine + ponciretin
show the reaction diagram
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S-adenosyl-L-methionine + (2S)-naringenin = S-adenosyl-L-homocysteine + ?
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S-adenosyl-L-methionine + naringenin = ?
show the reaction diagram
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S-adenosyl-L-methionine + naringenin = S-adenosyl-L-homocysteine + 4'-O-methylnaringenin
show the reaction diagram
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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-beta-D-glucoside
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UDPglucose + naringenin = ?
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UDP-alpha-D-glucose + naringenin = ?
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UDP-alpha-D-glucose + naringenin = UDP + naringenin-7-O-glucoside
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UDP-alpha-D-glucose + naringenin = UDP + ?
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sucrose + naringenin = D-fructose + naringenin glucoside
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UDP-alpha-D-glucose + naringenin = ? + UDP
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dimethylallyl diphosphate + naringenin = diphosphate + 6-(3-methylbut-2-enyl)naringenin
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3'-phosphoadenylylsulfate + naringenin = adenosine 3',5'-bisphosphate + ?
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naringenin + H2O = beta-D-glucose + naringenin
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Product in Enzyme-catalyzed Reactions (16 results)

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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)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (49 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
uncompetitive. The interaction is enthalpy driven and the microenvironment of aromatic residues is also altered. Naringenin inhibits fructosamine content by approximately 31.6% at 0.01 mM, and more than 93% inhibition of fluorescent advanced glycation end-products is achieved. Naringenin forms hydrogen bonds (Asn160 and Ile260), and two Pi-Pi interactions with Trp20 and one with His110
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very potent inhibitor, 0.02 mM inhibits by 71.9%
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above 0.1 mM
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0.010 mM, 50% inhibition, oxidation of androstandiol
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IC50: 0.336 mM
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non competitive with I-, competitive with H2O2
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IC50: 0.25 mM
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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
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1 mM: 72% inhibition, 0.1 mM: 54% inhibition
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42% inhibition at 0.1 mM
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might inhibit the enzyme
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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
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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) (42 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (14 results)

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

KM Value (48 results)

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

Ki Value (3 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00343
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pH 6.9, temperature not specified in the publication
0.012
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at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.007
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IC50 Value (16 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00037
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at pH 7.4 and 37°C
0.0215
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pH 6.9, temperature not specified in the publication
0.0026
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pH 6.2, 25°C
0.0024
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0.336
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IC50: 0.336 mM
0.25
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IC50: 0.25 mM
0.955
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0.0079
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25°C, pH 7.4, cell lysate
0.075
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pH 6.8, 30°C
0.0732
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at pH 2.0 and 37°C

References & Links

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Links to other databases for naringenin

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ChEBI
PubChem
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PubChem