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BRENDA support

Ligand berberine

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Basic Ligand Information

Molecular Structure
Picture of berberine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H18NO4
berberine
Synonyms:
5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizium

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
berberine + NADPH = canadine + NADP+
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-tetrahydroberberine + 2 O2 = berberine + 2 H2O2
show the reaction diagram
-
(R)-canadine + 2 NADP+ = berberine + 2 NADPH + H+
show the reaction diagram
-
(RS)-canadine + O2 = berberine + H2O2
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + berberine + NADPH + H+ = S-adenosyl-L-homocysteine + corydaline + NADP+
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
columbamine + O2 = berberine + H2O
show the reaction diagram
-
(S)-tetrahydroberberine + 2 O2 = berberine + 2 H2O2
show the reaction diagram
-
(R)-canadine + 2 NADP+ = berberine + 2 NADPH + H+
show the reaction diagram
-
(RS)-canadine + O2 = berberine + H2O2
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 4fold stimulation of ATPase activity
-

Inhibitor in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.023 mM, 50% inhibition
-
uncompetitive reversible potent IDO-1 inhibitor
-
50% inhibition at 0.004 mM
-
5 mM, 70% inhibition
-
10 mM, 50% inhibition
-
the ligand binds at the trimer-trimer interface, 24% inhibition at 0.005 mM with 500 ng enzyme
-
berberine affects kinetic constants of NAT, 24 h berberine treatment decreases bacterial growth and amounts of 2-acetylaminofluorene in Salmonella typhimurium by downregulation of the NAT enzyme expression
-
complete inhibition at 0.1 mM
-
an isoquinoline alkaloid derived from a plant used traditionally in Chinese and Ayurvedic medicine inhibits IKK activity. Addition of DTT to the kinase reaction reverses the berberine-mediated inhibition of IKK activity
-
suppresses MEK/ERK-dependent Egr-1 signaling pathway and inhibits vascular smooth muscle cell regrowth after mechanical injury in vitro
-
binding structure, molecular modeling, overview
-
reversible non-competitive inhibition
-
16% inhibition at 0.1 mM
-
inhibition of the ACE2 enzyme
-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.005
-
-

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.025
-
pH 9.9
0.008
-
pH and temperature not specified in the publication
10
-
-
0.021
-
at pH 8.9, temperature not specified in the publication
0.000289
-
pH 8.0, 37°C

IC50 Value (18 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0093
-
pH and temperature not specified in the publication
0.087
-
at pH 8.9, temperature not specified in the publication
0.0135
-
in 50 mM sodium acetate buffer (pH 5.0), at 22°C
0.0133
-
in Tris buffer (pH 7.5, 50 mM), at 37°C
0.00804
-
pH and temperature not specified in the publication
0.0523
-
in 50 mM Tris-HCl, pH 7.0, at 37°C
0.1
-
IC50 above 0.1 mM, pH and temperature not specified in the publication

References & Links

Links to other databases for berberine

ChEBI
PubChem
ChEBI
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