Ligand baicalein

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Basic Ligand Information

Molecular Structure
Picture of baicalein (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O5
baicalein
FXNFHKRTJBSTCS-UHFFFAOYSA-N
Synonyms:
5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one, 5,6,7-trihydroxyflavone

Show all pahtways known for Show all pathways known for baicalein

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
baicalin + H2O = baicalein + D-glucuronate
show the reaction diagram
-
-
baicalin + H2O = baicalein + beta-D-glucuronic acid
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-glucose + baicalein = UDP + 7-O-glucosylbaicalein
show the reaction diagram
-
UDP-glucose + baicalein = UDP + baicalein 7-O-beta-D-glucoside
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (40 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 25% inhibition at 0.0025 mM
-
affects fungal pigmentation and growth, inhibits by 75%
-
IC50: 0.0012 mM
-
uncompetitive reversible potent IDO-1 inhibitor
-
5,6,7-trihydroxyflavone, high inhibitory effects on tyrosinase. Acts as a cofactor to monophenolase
-
50% inhibition at 0.11169 mM
-
50% inhibition of phosphorylated, active enzyme at 0.0112 mM, 50% inhibition of unphosphorylated, adenosine monophosphate-activated enzyme at 0.0102 mM
-
an alkaloid isolated from Isatis tinctoria
-
42% inhibition at 0.3 mM
-
(5,6,7-trihydroxyflavone), naturally occurring flavone, isolated from the stem-bark of Oroxylum indicum, binds to the free enzyme and also intercalates into the DNA at a very high concentration (300 mM) without binding to the minor grove
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

KM Value (1 result)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0524
-
pH 7.5, 37°C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0054
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.215
-
pH and temperature not specified in the publication
0.5
-
-

IC50 Value (21 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.012
-
at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C
0.0012
-
IC50: 0.0012 mM
0.273
-
-
0.52
-
pH 5.5, 20°C
0.0123
-
at pH 7.0 and 25°C
0.06
-
pH and temperature not specified in the publication
0.011
-
indicate that the hydroxy groups at the B ring of flavonoids contribute to the human GLO I inhibitory activity of the flavonoid compounds at 25°C, pH 7.0

References & Links

Links to other databases for baicalein

ChEBI
PubChem
ChEBI
PubChem