BRENDA - Enzyme Database
show all sequences of 5.3.2.1

Macrophage migration inhibitory factor (MIF) tautomerase inhibitors as potential novel anti-inflammatory agents: current developments

Garai, J.; Lorand, T.; Curr. Med. Chem. 16, 1091-1114 (2009)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
Homo sapiens
(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
Homo sapiens
(2E)-2-(2-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(3-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-bromobenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-chlorobenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-methoxybenzylidene)cyclohexanone
-
Homo sapiens
(2E)-2-(4-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(pyridin-2-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-(pyridin-3-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-(pyridin-4-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-benzylidene-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-benzylidenecyclohexanone
-
Homo sapiens
(2E)-2-benzylidenecyclopentanone
-
Homo sapiens
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
Homo sapiens
(2E)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoic acid
-
Homo sapiens
(2E,5E)-2,5-dibenzylidenecyclopentanone
-
Homo sapiens
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
-
Homo sapiens
(E)-2-fluoro-4-hydroxycinnamate
competitive inhibition
Homo sapiens
(E)-2-fluoro-cinnamate
-
Homo sapiens
(E)-2-fluorocinnamate
-
Homo sapiens
(E)-4-hydroxycinnamate
-
Homo sapiens
(E)-cinnamate
-
Homo sapiens
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
i.e. ISO-I
Homo sapiens
(S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(Z)-2-fluoro-4-hydroxycinnamate
-
Homo sapiens
(Z)-2-fluoro-cinnamate
-
Homo sapiens
(Z)-2-fluorocinnamate
-
Homo sapiens
(Z)-4-hydroxycinnamate
-
Homo sapiens
(Z)-cinnamate
-
Homo sapiens
2,2-dimethylpropyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,2-dimethylpropyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,4,6-trimethylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,5-dibenzylidenecyclopentanone
-
Homo sapiens
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
Homo sapiens
2-oxo-4-phenylbut-3-ynoic acid
inhibition mechanism, overview
Homo sapiens
2-propionylcyclohexanone
-
Homo sapiens
2-[3,6-bis(diethylamino)-3H-xanthen-9-yl]-5-[(6-{[4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]amino}-6-oxohexyl)sulfamoyl]benzenesulfonic acid
-
Homo sapiens
2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-N-(4-methoxyphenyl)acetamide
-
Homo sapiens
3,4-dihydroxycyclohexa-2,5-diene-1-carboxylic acid
-
Homo sapiens
3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid
-
Homo sapiens
3,6-dihydroxy-1-methyl-5-oxo-3,5-dihydro-2H-indolium
-
Homo sapiens
3,6-dihydroxy-2-methyl-2,3-dihydro-5H-indol-5-one
-
Homo sapiens
3,6-dihydroxy-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
Homo sapiens
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
-
Homo sapiens
3-acetyl-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
3-hydroxy-acetaminophen
-
Homo sapiens
3-hydroxybutyrate
-
Homo sapiens
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
4-coumaric acid
-
Homo sapiens
4-methoxyphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
4-tert-butylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
-
Homo sapiens
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-phenyl-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
-
Homo sapiens
acetaminophen
-
Homo sapiens
acetoacetate
-
Homo sapiens
acetone
-
Homo sapiens
Acetylacetone
-
Homo sapiens
AVP-13546
inhibits the tautomerase activity of MIF and reduces cytokine, including TNF-alpha, levels in vivo
Homo sapiens
boldine
-
Homo sapiens
butyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
caffeate
-
Homo sapiens
carnosic acid
-
Homo sapiens
chlorogenic acid
-
Homo sapiens
coumarin
-
Homo sapiens
curcumin
-
Homo sapiens
cyclohexyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
cyclohexylmethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
-
Homo sapiens
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
inhibition mechanism, overview
Homo sapiens
ethyl acetoacetate
-
Homo sapiens
ethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
ferulic acid
-
Homo sapiens
iodoacetamide
-
Homo sapiens
methyl 6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylate
-
Homo sapiens
methyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
additional information
there exist several classes of inhibitors that are active against MIF tautomerase activity, overview. No activity by (S,R)-3-(4-methoxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester and isoxazole and its reduced derivative
Homo sapiens
N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(3,4-dimethoxyphenyl)acetamide
-
Homo sapiens
N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(3-methyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(4-aminobutyl)-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
Homo sapiens
N-(4-hydroxy-3-methoxycyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(4-hydroxy-3-methoxyphenyl)acetamide
-
Homo sapiens
N-acetyl-3-hydroxy-4-benzoquinone imine
-
Homo sapiens
N-acetyl-4-benzoquinone imine
-
Homo sapiens
N-cyclohexyl-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
Homo sapiens
NEM
-
Homo sapiens
phenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
phloretin
-
Homo sapiens
propan-2-yl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
propyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
resveratrol
-
Homo sapiens
rosmarinic acid
-
Homo sapiens
tert-butyl [4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]carbamate
-
Homo sapiens
umbelliferone
-
Homo sapiens
VGX-1027
-
Homo sapiens
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
keto-(4-hydroxyphenyl)pyruvate
Homo sapiens
-
enol-(4-hydroxyphenyl)pyruvate
-
-
r
keto-phenylpyruvate
Homo sapiens
-
enol-phenylpyruvate
-
-
r
additional information
Homo sapiens
the MIF protein is multifunctional, exhibiting besides its tautomerase activity, e.g. also L-dopachrome isomerase activity, EC 5.3.3.12, and thioredoxin-like function, or its cytokine function, overview
?
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Homo sapiens
-
-
-
Source Tissue
Source Tissue
Commentary
Organism
Textmining
endothelial cell
-
Homo sapiens
-
eosinophil
-
Homo sapiens
-
macrophage
-
Homo sapiens
-
pituitary gland
corticotrop cells
Homo sapiens
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
keto-(4-hydroxyphenyl)pyruvate
-
703331
Homo sapiens
enol-(4-hydroxyphenyl)pyruvate
-
-
-
r
keto-phenylpyruvate
-
703331
Homo sapiens
enol-phenylpyruvate
-
-
-
r
additional information
the MIF protein is multifunctional, exhibiting besides its tautomerase activity, e.g. also L-dopachrome isomerase activity, EC 5.3.3.12, and thioredoxin-like function, or its cytokine function, overview
703331
Homo sapiens
?
-
-
-
?
additional information
the N-terminal Pro is essential for the tautomerase activity of MIF
703331
Homo sapiens
?
-
-
-
?
Subunits
Subunits
Commentary
Organism
trimer
the tertiary structure is stabilized by hydrogen bonds and a hydrophobic core, three beta-sheets and six alpha-helices surround a traversing channel with dominant positive charge in the middle of the trimer, structure, overview. The enzyme contains a Cys-Xaa-Xaa-Cys motif required for oxido-reductase activity and MIF-like activities like glucorticoid overriding and cell proliferation
Homo sapiens
Synonyms
Synonyms
Commentary
Organism
macrophage migration inhibitory factor tautomerase
-
Homo sapiens
MIF tautomerase
-
Homo sapiens
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.000038
-
-
Homo sapiens
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
0.00028
-
-
Homo sapiens
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
0.00047
-
-
Homo sapiens
7-hydroxy-3-phenyl-2H-chromen-2-one
0.0005
-
-
Homo sapiens
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
0.00055
-
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
0.0007
-
-
Homo sapiens
N-acetyl-3-hydroxy-4-benzoquinone imine
0.0013
-
-
Homo sapiens
AVP-13546
0.0015
-
-
Homo sapiens
(E)-4-hydroxycinnamate
0.0015
-
-
Homo sapiens
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
0.0016
-
-
Homo sapiens
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
0.00161
-
-
Homo sapiens
2,5-dibenzylidenecyclopentanone
0.0021
-
-
Homo sapiens
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
0.0026
-
-
Homo sapiens
(E)-2-fluoro-4-hydroxycinnamate
0.0029
-
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
0.0031
-
-
Homo sapiens
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
0.0043
-
-
Homo sapiens
3-acetyl-7-hydroxy-2H-chromen-2-one
0.0058
-
-
Homo sapiens
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
0.0062
-
-
Homo sapiens
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
0.007
-
-
Homo sapiens
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
0.0074
-
-
Homo sapiens
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
0.013
-
-
Homo sapiens
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
0.04
-
-
Homo sapiens
N-acetyl-4-benzoquinone imine
0.073
-
-
Homo sapiens
(E)-2-fluoro-cinnamate
0.073
-
-
Homo sapiens
(E)-2-fluorocinnamate
0.21
-
-
Homo sapiens
(Z)-4-hydroxycinnamate
0.48
-
-
Homo sapiens
(Z)-2-fluoro-4-hydroxycinnamate
0.5
-
-
Homo sapiens
3-hydroxy-acetaminophen
2.33
-
-
Homo sapiens
(Z)-2-fluorocinnamate
2.33
-
-
Homo sapiens
(Z)-2-fluoro-cinnamate
10
-
-
Homo sapiens
acetaminophen
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.000038
-
-
Homo sapiens
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
0.00028
-
-
Homo sapiens
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
0.00047
-
-
Homo sapiens
7-hydroxy-3-phenyl-2H-chromen-2-one
0.0005
-
-
Homo sapiens
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
0.00055
-
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
0.0007
-
-
Homo sapiens
N-acetyl-3-hydroxy-4-benzoquinone imine
0.0013
-
-
Homo sapiens
AVP-13546
0.0015
-
-
Homo sapiens
(E)-4-hydroxycinnamate
0.0015
-
-
Homo sapiens
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
0.0016
-
-
Homo sapiens
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
0.00161
-
-
Homo sapiens
2,5-dibenzylidenecyclopentanone
0.0021
-
-
Homo sapiens
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
0.0026
-
-
Homo sapiens
(E)-2-fluoro-4-hydroxycinnamate
0.0029
-
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
0.0031
-
-
Homo sapiens
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
0.0043
-
-
Homo sapiens
3-acetyl-7-hydroxy-2H-chromen-2-one
0.0058
-
-
Homo sapiens
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
0.0062
-
-
Homo sapiens
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
0.007
-
-
Homo sapiens
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
0.0074
-
-
Homo sapiens
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
0.013
-
-
Homo sapiens
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
0.04
-
-
Homo sapiens
N-acetyl-4-benzoquinone imine
0.073
-
-
Homo sapiens
(E)-2-fluoro-cinnamate
0.073
-
-
Homo sapiens
(E)-2-fluorocinnamate
0.21
-
-
Homo sapiens
(Z)-4-hydroxycinnamate
0.48
-
-
Homo sapiens
(Z)-2-fluoro-4-hydroxycinnamate
0.5
-
-
Homo sapiens
3-hydroxy-acetaminophen
2.33
-
-
Homo sapiens
(Z)-2-fluorocinnamate
2.33
-
-
Homo sapiens
(Z)-2-fluoro-cinnamate
10
-
-
Homo sapiens
acetaminophen
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
Homo sapiens
(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
Homo sapiens
(2E)-2-(2-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(3-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-bromobenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-chlorobenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(4-methoxybenzylidene)cyclohexanone
-
Homo sapiens
(2E)-2-(4-methoxybenzylidene)cyclopentanone
-
Homo sapiens
(2E)-2-(pyridin-2-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-(pyridin-3-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-(pyridin-4-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-benzylidene-3,4-dihydronaphthalen-1(2H)-one
-
Homo sapiens
(2E)-2-benzylidenecyclohexanone
-
Homo sapiens
(2E)-2-benzylidenecyclopentanone
-
Homo sapiens
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
Homo sapiens
(2E)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoic acid
-
Homo sapiens
(2E,5E)-2,5-dibenzylidenecyclopentanone
-
Homo sapiens
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
-
Homo sapiens
(E)-2-fluoro-4-hydroxycinnamate
competitive inhibition
Homo sapiens
(E)-2-fluoro-cinnamate
-
Homo sapiens
(E)-2-fluorocinnamate
-
Homo sapiens
(E)-4-hydroxycinnamate
-
Homo sapiens
(E)-cinnamate
-
Homo sapiens
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
i.e. ISO-I
Homo sapiens
(S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
Homo sapiens
(Z)-2-fluoro-4-hydroxycinnamate
-
Homo sapiens
(Z)-2-fluoro-cinnamate
-
Homo sapiens
(Z)-2-fluorocinnamate
-
Homo sapiens
(Z)-4-hydroxycinnamate
-
Homo sapiens
(Z)-cinnamate
-
Homo sapiens
2,2-dimethylpropyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,2-dimethylpropyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,4,6-trimethylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
2,5-dibenzylidenecyclopentanone
-
Homo sapiens
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
Homo sapiens
2-oxo-4-phenylbut-3-ynoic acid
inhibition mechanism, overview
Homo sapiens
2-propionylcyclohexanone
-
Homo sapiens
2-[3,6-bis(diethylamino)-3H-xanthen-9-yl]-5-[(6-{[4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]amino}-6-oxohexyl)sulfamoyl]benzenesulfonic acid
-
Homo sapiens
2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-N-(4-methoxyphenyl)acetamide
-
Homo sapiens
3,4-dihydroxycyclohexa-2,5-diene-1-carboxylic acid
-
Homo sapiens
3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid
-
Homo sapiens
3,6-dihydroxy-1-methyl-5-oxo-3,5-dihydro-2H-indolium
-
Homo sapiens
3,6-dihydroxy-2-methyl-2,3-dihydro-5H-indol-5-one
-
Homo sapiens
3,6-dihydroxy-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
Homo sapiens
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
-
Homo sapiens
3-acetyl-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
3-hydroxy-acetaminophen
-
Homo sapiens
3-hydroxybutyrate
-
Homo sapiens
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
-
Homo sapiens
4-coumaric acid
-
Homo sapiens
4-methoxyphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
4-tert-butylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
-
Homo sapiens
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
-
Homo sapiens
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-phenyl-2H-chromen-2-one
-
Homo sapiens
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
-
Homo sapiens
acetaminophen
-
Homo sapiens
acetoacetate
-
Homo sapiens
acetone
-
Homo sapiens
Acetylacetone
-
Homo sapiens
AVP-13546
inhibits the tautomerase activity of MIF and reduces cytokine, including TNF-alpha, levels in vivo
Homo sapiens
boldine
-
Homo sapiens
butyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
caffeate
-
Homo sapiens
carnosic acid
-
Homo sapiens
chlorogenic acid
-
Homo sapiens
coumarin
-
Homo sapiens
curcumin
-
Homo sapiens
cyclohexyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
cyclohexylmethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
-
Homo sapiens
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
inhibition mechanism, overview
Homo sapiens
ethyl acetoacetate
-
Homo sapiens
ethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
ferulic acid
-
Homo sapiens
iodoacetamide
-
Homo sapiens
methyl 6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylate
-
Homo sapiens
methyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
additional information
there exist several classes of inhibitors that are active against MIF tautomerase activity, overview. No activity by (S,R)-3-(4-methoxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester and isoxazole and its reduced derivative
Homo sapiens
N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(3,4-dimethoxyphenyl)acetamide
-
Homo sapiens
N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(3-methyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(4-aminobutyl)-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
Homo sapiens
N-(4-hydroxy-3-methoxycyclohexa-2,5-dien-1-yl)acetamide
-
Homo sapiens
N-(4-hydroxy-3-methoxyphenyl)acetamide
-
Homo sapiens
N-acetyl-3-hydroxy-4-benzoquinone imine
-
Homo sapiens
N-acetyl-4-benzoquinone imine
-
Homo sapiens
N-cyclohexyl-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
Homo sapiens
NEM
-
Homo sapiens
phenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
phloretin
-
Homo sapiens
propan-2-yl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
propyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
Homo sapiens
resveratrol
-
Homo sapiens
rosmarinic acid
-
Homo sapiens
tert-butyl [4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]carbamate
-
Homo sapiens
umbelliferone
-
Homo sapiens
VGX-1027
-
Homo sapiens
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
keto-(4-hydroxyphenyl)pyruvate
Homo sapiens
-
enol-(4-hydroxyphenyl)pyruvate
-
-
r
keto-phenylpyruvate
Homo sapiens
-
enol-phenylpyruvate
-
-
r
additional information
Homo sapiens
the MIF protein is multifunctional, exhibiting besides its tautomerase activity, e.g. also L-dopachrome isomerase activity, EC 5.3.3.12, and thioredoxin-like function, or its cytokine function, overview
?
-
-
?
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
endothelial cell
-
Homo sapiens
-
eosinophil
-
Homo sapiens
-
macrophage
-
Homo sapiens
-
pituitary gland
corticotrop cells
Homo sapiens
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
keto-(4-hydroxyphenyl)pyruvate
-
703331
Homo sapiens
enol-(4-hydroxyphenyl)pyruvate
-
-
-
r
keto-phenylpyruvate
-
703331
Homo sapiens
enol-phenylpyruvate
-
-
-
r
additional information
the MIF protein is multifunctional, exhibiting besides its tautomerase activity, e.g. also L-dopachrome isomerase activity, EC 5.3.3.12, and thioredoxin-like function, or its cytokine function, overview
703331
Homo sapiens
?
-
-
-
?
additional information
the N-terminal Pro is essential for the tautomerase activity of MIF
703331
Homo sapiens
?
-
-
-
?
Subunits (protein specific)
Subunits
Commentary
Organism
trimer
the tertiary structure is stabilized by hydrogen bonds and a hydrophobic core, three beta-sheets and six alpha-helices surround a traversing channel with dominant positive charge in the middle of the trimer, structure, overview. The enzyme contains a Cys-Xaa-Xaa-Cys motif required for oxido-reductase activity and MIF-like activities like glucorticoid overriding and cell proliferation
Homo sapiens
Expression
Organism
Commentary
Expression
Homo sapiens
MIF expression is upregulated by cytokines, TNF-alpha and interleukin-I, and by bacterial endotoxins, such as lipopolysaccharides, and exotoxins
up
General Information
General Information
Commentary
Organism
malfunction
MIF expression contributes to cell proliferation, invasiveness and neo-angiogenesis of neuroblastoma, gastric, hepatocellularbladder, and breast carcinomas. MIF takes part in the pathogenesis of Alzheimer's disease and multiple sklerosis
Homo sapiens
physiological function
MIF plays an essential role in both, innate and adaptive immune response. It is implicated in tumor growth and angiogenesis, an exerts an antagonistic effect against glucocorticoid immunosuppressive action, and shows glucorticoid overriding activity
Homo sapiens
General Information (protein specific)
General Information
Commentary
Organism
malfunction
MIF expression contributes to cell proliferation, invasiveness and neo-angiogenesis of neuroblastoma, gastric, hepatocellularbladder, and breast carcinomas. MIF takes part in the pathogenesis of Alzheimer's disease and multiple sklerosis
Homo sapiens
physiological function
MIF plays an essential role in both, innate and adaptive immune response. It is implicated in tumor growth and angiogenesis, an exerts an antagonistic effect against glucocorticoid immunosuppressive action, and shows glucorticoid overriding activity
Homo sapiens
Expression (protein specific)
Organism
Commentary
Expression
Homo sapiens
MIF expression is upregulated by cytokines, TNF-alpha and interleukin-I, and by bacterial endotoxins, such as lipopolysaccharides, and exotoxins
up
Other publictions for EC 5.3.2.1
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [C]
Temperature Range [C]
Temperature Stability [C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [C] (protein specific)
Temperature Range [C] (protein specific)
Temperature Stability [C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
714241
Baas
Characterization of a newly id ...
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis mc(2)155
Biochemistry
50
2889-2899
2011
-
-
1
-
1
-
1
7
-
-
3
-
-
10
-
-
1
-
-
-
-
-
11
2
7
-
-
-
7
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
1
-
7
-
-
3
-
-
-
-
1
-
-
-
-
11
2
-
-
-
7
-
-
-
-
-
-
-
-
8
8
716749
Cho
Allosteric inhibition of macro ...
Homo sapiens
Proc. Natl. Acad. Sci. USA
107
11313-11318
2010
-
-
-
1
-
-
3
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
2
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
1
-
-
-
3
3
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
702357
Ouertatani-Sakouhi
A new class of isothiocyanate- ...
Homo sapiens
Biochemistry
48
9858-9870
2009
-
1
1
-
1
-
6
-
-
-
-
2
-
1
-
-
1
-
-
-
-
-
2
1
2
-
-
-
-
-
-
-
-
-
-
5
-
1
1
-
-
1
-
5
6
-
-
-
-
-
2
-
-
-
1
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
2
2
-
-
-
703331
Garai
Macrophage migration inhibitor ...
Homo sapiens
Curr. Med. Chem.
16
1091-1114
2009
-
-
-
-
-
-
105
-
-
-
-
3
-
3
-
-
-
-
-
4
-
-
4
1
2
-
-
-
-
-
-
-
-
-
-
30
-
-
-
-
-
-
-
30
105
-
-
-
-
-
3
-
-
-
-
-
4
-
-
4
1
-
-
-
-
-
-
-
-
1
2
2
1
-
-
691702
Poelarends
The chemical versatility of th ...
Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
Cell. Mol. Life Sci.
65
3606-3618
2008
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
-
2
1
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
678327
Poelarends
Phenylpyruvate tautomerase act ...
Mus musculus, Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
Biochemistry
46
9596-9604
2007
-
-
-
-
4
-
-
4
-
-
-
-
-
4
-
-
-
-
-
-
-
-
3
-
1
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
680173
Garai
MIF tautomerase inhibitor pote ...
Bos taurus
Int. Immunopharmacol.
7
1741-1746
2007
-
-
-
-
-
-
7
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
7
-
-
-
-
-
-
-
7
7
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
678357
Cherepkova
Macrophage migration inhibitor ...
Bos taurus
Biochemistry (Moscow)
71
73-78
2006
-
-
-
-
-
-
-
-
2
-
1
-
-
4
-
-
1
-
-
5
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
1
-
-
-
-
1
-
5
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
678575
Golubkov
Inactivation of the phenylpyru ...
Mus musculus
Bioorg. Chem.
34
183-199
2006
-
-
1
1
1
-
1
2
-
-
-
-
-
3
-
-
-
-
-
-
-
-
2
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
1
-
1
1
-
-
1
-
2
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
661889
Molnar
Plant-derived anti-inflammator ...
Bos taurus
Int. Immunopharmacol.
5
849-856
2005
-
-
-
-
-
-
27
-
-
-
-
-
-
3
-
-
-
-
-
1
-
-
1
-
2
-
-
-
-
-
-
-
-
-
-
45
-
-
-
-
-
-
-
45
27
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
652330
Zang
Homologues of human macrophage ...
Brugia malayi
J. Biol. Chem.
277
44261-44267
2002
-
-
1
1
-
-
-
-
-
-
1
1
-
9
-
-
-
-
-
2
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
2
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
650013
Stamps
Mechanism of the phenylpyruvat ...
Mus musculus
Biochemistry
39
9671-9678
2000
-
-
1
1
4
-
1
10
-
-
5
-
-
1
-
-
-
-
-
-
-
-
2
5
-
-
-
-
10
-
-
-
-
1
-
-
-
-
1
-
1
4
-
-
1
1
10
-
-
5
-
-
-
-
-
-
-
-
-
2
5
-
-
-
10
-
-
-
-
-
-
-
-
-
-
649866
Hermanowski-Vosatka
Enzymatically inactive macroph ...
Mus musculus
Biochemistry
38
12841-12849
1999
-
-
1
-
2
-
-
-
-
-
-
1
-
2
-
-
1
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
1
-
-
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
649881
Johnson
A kinetic and stereochemical i ...
Mus musculus
Biochemistry
38
16024-16033
1999
-
-
-
-
2
-
2
6
-
-
3
-
-
1
-
-
-
-
-
-
-
-
2
3
2
-
-
-
6
-
-
-
-
4
-
-
-
-
-
-
-
2
-
-
2
4
6
-
-
3
-
-
-
-
-
-
-
-
-
2
3
-
-
-
6
-
-
-
-
-
-
-
-
-
-
649900
Lubetsky
Pro-1 of macrophage migration ...
Homo sapiens
Biochemistry
38
7346-7354
1999
-
-
-
1
2
-
-
-
-
-
1
1
-
3
-
-
-
-
-
-
-
-
2
1
1
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
1
2
-
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
2
1
-
-
-
4
-
-
-
-
-
-
-
-
-
-
649901
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1977
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2868
Knox
Enzymic catalysis of the keto- ...
Bos taurus, Canis lupus familiaris, Cavia porcellus, Oryctolagus cuniculus, Equus caballus, Neurospora sp., no activity in Aerobacter sp., Pseudomonas sp., Rattus norvegicus, Sus scrofa
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