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BRENDA support

Ligand cyanidin

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Basic Ligand Information

Molecular Structure
Picture of cyanidin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O6
cyanidin
VEVZSMAEJFVWIL-UHFFFAOYSA-O
Synonyms:
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenium

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cyanidin + NADPH + H+ = (-)-epicatechin + NADP+ + H2O
show the reaction diagram
-
UDP-alpha-D-glucose + cyanidin = UDP + cyanidin 3-O-beta-D-glucoside
show the reaction diagram
-
UDP-alpha-D-galactose + cyanidin = UDP + cyanidin 3-O-beta-D-galactoside
show the reaction diagram
-
UDP-alpha-D-glucose + cyanidin = UDP + cyanidin 3-O-beta-D-glucoside
show the reaction diagram
-

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cyanidin-3-O-beta-D-glucoside + H2O = cyanidin + beta-D-glucose
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + cyanidin = S-adenosyl-L-homocysteine + 3'-methoxycyanidin
show the reaction diagram
-
UDP-alpha-D-galactose + cyanidin = UDP + cyanidin 3-O-beta-D-galactoside
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cyanidin-3-O-beta-D-glucoside + H2O = cyanidin + beta-D-glucose
show the reaction diagram
-

Inhibitor in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
from Aronia melanocarpa concentrate, inhibits in a concentration-dependent manner
-
competitive interaction of cyanidin with MAO A plus a mixed competitive and non-competitive mode of interaction of cyanidin with MAO B
-
50% inhibition of phosphorylated, active enzyme at 0.003 mM, 50% inhibition of unphosphorylated, adenosine monophosphate-activated enzyme at 0.009 mM
-
the recombinant enzyme exhibits pronounced substrate inhibition by cyanidin at 0.1 mM
-
mixed competitive and noncompetitive inhibition, partial hyperbolic type of inhibition
-
anthocyanidin, complete inhibition of enzyme, isozyme IIalpha and IIbeta, decatenation activity at 0.01 mM, no stabilization of the DNA-enzyme intermediate in contrast to topoisomerase poisons
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (12 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.000704
-
in 100 mM Tris-HCl pH 8.0, at 30°C
0.000702
-
in 100 mM Tris-HCl pH 8.0, at 30°C

KM Value (21 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0028
-
pH 7.5, 30°C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.035
-
-
0.0021
-
in an aqueous buffer solution, pH 7.5, containing 94 mM KCl, 9 mM CaCl2, 24 mM Tris and 0.28 mM Triton-X 100

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.58
-
-
0.0295
-
pH not specified in the publication, temperature not specified in the publication, MAO-A
0.004
-
pH 6.8, 30°C
0.0023
-
at 37°C in 10 mM potassium phosphate buffer, pH 7.4, containing 0.05% (w/v) emulphogen
0.0218
-
at 37°C in 10 mM potassium phosphate buffer, pH 7.4, containing 0.05% (w/v) emulphogene

References & Links

Links to other databases for cyanidin

ChEBI
PubChem
ChEBI
PubChem