Ligand curcumin

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Basic Ligand Information

Molecular Structure
Picture of curcumin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C21H20O6
curcumin
VFLDPWHFBUODDF-FCXRPNKRSA-N
Synonyms:
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione, trans,trans-curcumin

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
UDP-D-glucuronate + curcumin = UDP + curcumin phenolic beta-D-monoglucuronide
show the reaction diagram
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curcumin + H2O = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2 feruloyl-CoA + malonyl-CoA + H2O = 3 CoA + curcumin + 2 CO2
show the reaction diagram
-
-
feruloyl-CoA + feruloylacetyl-CoA + H2O = 2 CoA + curcumin + CO2
show the reaction diagram
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-
curcumin-beta-D-glucuronide + H2O = curcumin + beta-D-glucuronic acid
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
curcumin + H2O2 + H+ = ?
show the reaction diagram
-
curcumin + NAD(P)H = ?
show the reaction diagram
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TDP-glucose + curcumin = TDP + 7-O-beta-D-glucosyl-curcumin
show the reaction diagram
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curcumin + H2O = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
feruloyl-CoA + feruloylacetyl-CoA + H2O = 2 CoA + curcumin + CO2
show the reaction diagram
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-
curcumin-bis-alpha-D-glucoside + H2O = curcumin + beta-D-glucose
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits or activates PKC dependent on Ca2+ and the presence of membranes or phosphatidylserine, respectively, in presence of phosphatidylserine curcumin activates PKC, in presence of membranes with phosphatidylserine the enzyme is inhibited, Ca2+ competes with curcumin at the regulatory domainbinding site, overview, effects on different isozymes, overview
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molecular basis for Fe(III)-independent curcumin potentiation of cystic fibrosis transmembrane conductance regulator activity, overview. Highly conserved aromatic and positively charged residues at the ICL1/ICL4 interface and phosphorylation site S813 are sensitive to curcumin regardless of whether Fe3+ and nucleotide-binding domain 2 are removed. Spontaneous disulfide cross-linking between curcumin-sensitive ICL1 and S795 is observed to be enough to promote channel opening as curcumin does. Curcumin may potentiate CFTR activity not only by removing inhibitory Fe3+ to release the R domain from ICL3 but also by stabilizing the stimulatory R-ICL1/ICL4 interactions
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Inhibitor in Enzyme-catalyzed Reactions (86 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM, 50% inhibition
-
inhibitory against isoform 11beta-HSD2 in intact cells with IC50 value of 14.56 microM
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moderate inhibition
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complete inhibition at 0.3 mM
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i.e. (E,E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, an uncompetitive inhibition of FabI, shows antibacterial activity against Escherichia coli, sensitivity is decreased in FabI-overexpressing Escherichia coli
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inhibition of enzyme activity in vivo and in vitro. Inducues dissociation of complexes of enzyme with tumor suppressor protein p53 leading to degradation of p53, but not of p53 cancer hot-spot mutant R273H
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25 microM inhibit histidine-tagged recombinant p300 with purified human HeLa core histone as substrate by about 75%
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downregulates expression of isoform ST3GAL5
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inhibits both the free enzyme and the COP9 signalosome complex-associated kinase
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weak inhibition of IKK-2
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inhibits or activates PKC dependent on Ca2+ and the presence of membranes or phosphatidylserine, respectively, in presence of phosphatidylserine curcumin activates PKC, in presence of membranes with phosphatidylserine the enzyme is inhibited, Ca2+ competes with curcumin at the regulatory domainbinding site, overview, effects on different isozymes, overview
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curcumin strongly interacts with isoform CAMK4
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reversible inhibition
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inhibits acid SMase, but not neutral and alkaline SMase, in Caco-2 cells with an antiproliferative effect, the effect is more potent in monolayers than in polarised cells, metabolis effects, overview
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the lower affinity first generation inhibitor does not distinguish between isozymes PLD1 and 2
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60% inhibition at 0.1 mM
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is inhibitory at higher concentrations
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non-competitive inhibitor
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inhibition of the ACE2 enzyme
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treatment of whole cell, significant inhibition of enzyme activity after 15 days with concomitant decrease in expression of membrane type-1 matrix metalloproteinase and focal adhesion kinase to almost background level
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inhibits by both decreasing catalytic capacity and increasing substrate affinity
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highly potent HDAC inhibitor, 52% residual activity at 0.5 mM
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slight inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

KM Value (4 results)

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

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0997
-
pH not specified in the publication, temperature not specified in the publication
0.0169
-
-
0.015
-
pH 7.5, 22°C
0.0003
-
pH 7.4, 37°C
0.046
-
at pH 7.4 and 28°C
0.000036
-
pH and temperature not specified in the publication
0.000539
-
pH and temperature not specified in the publication

IC50 Value (25 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0154
-
IC50: 0.0154 mM, noncompetitive inhibition with respect to shikimate and NADP+
0.0134
-
at pH 7.4 and 37°C
0.00004
0.005
pH 7.4, 30°C, purified recombinant isozymes GST A1-1, A2-2, M1-1, M2-2, and P1-1
0.0124
-
pH 7.4, 37°C
0.006
-
in 50 mM sodium acetate buffer (pH 5.0), at 22°C
0.057
-
IC50 is 0.057 mM
0.0915
-
pH and temperature not specified in the publication
0.115
-
pH and temperature not specified in the publication

References & Links

Links to other databases for curcumin

ChEBI
PubChem
ChEBI
PubChem