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5.3.2.1: phenylpyruvate tautomerase

This is an abbreviated version!
For detailed information about phenylpyruvate tautomerase, go to the full flat file.

Word Map on EC 5.3.2.1

Reaction

keto-phenylpyruvate
=
enol-phenylpyruvate

Synonyms

CaaD, CCH2, cis-3-chloroacrylic acid dehalogenase, cis-CaaD, Macrophage migration inhibitory factor, macrophage migration inhibitory factor tautomerase, MIF, MIF tautomerase, phenyl(enol)pyruvate tautomerase, Phenylpyruvate keto-enol tautomerase, Phenylpyruvic keto-enol isomerase, PPT, Tautomerase, phenylpyruvate, trans-3-chloroacrylic acid dehalogenase

ECTree

     5 Isomerases
         5.3 Intramolecular oxidoreductases
             5.3.2 Interconverting keto- and enol-groups
                5.3.2.1 phenylpyruvate tautomerase

Inhibitors

Inhibitors on EC 5.3.2.1 - phenylpyruvate tautomerase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
-
(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
-
-
(2E)-2-(2-methoxybenzylidene)cyclopentanone
-
-
(2E)-2-(3-methoxybenzylidene)cyclopentanone
-
-
(2E)-2-(4-bromobenzylidene)cyclopentanone
-
-
(2E)-2-(4-chlorobenzylidene)cyclopentanone
-
-
(2E)-2-(4-methoxybenzylidene)cyclohexanone
-
-
(2E)-2-(4-methoxybenzylidene)cyclopentanone
-
-
(2E)-2-(pyridin-2-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
-
(2E)-2-(pyridin-3-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
-
(2E)-2-(pyridin-4-ylmethylidene)-3,4-dihydronaphthalen-1(2H)-one
-
-
(2E)-2-benzylidene-3,4-dihydronaphthalen-1(2H)-one
-
-
(2E)-2-benzylidenecyclohexanone
-
-
(2E)-2-benzylidenecyclopentanone
-
-
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
-
-
(2E)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoic acid
-
-
(2E,5E)-2,5-dibenzylidenecyclopentanone
-
-
(2Z)-2-(2-methoxybenzylidene)cyclopentanone
-
-
(2Z)-2-(4-bromobenzylidene)cyclopentanone
-
-
(2Z)-2-(4-methoxybenzylidene)cyclohexanone
-
-
(2Z)-2-(4-methoxybenzylidene)cyclopentanone
-
-
(2Z)-2-(pyridin-2-ylmethylene)-3,4-dihydronaphthalen-1(2H)-one
-
-
(2Z)-2-benzylidenecyclopentanone
-
-
(2Z,5Z)-2,5-dibenzylidenecyclopentanone
-
-
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
-
-
(E)-2-fluoro-4-hydroxycinnamate
-
competitive inhibition
(E)-2-fluoro-cinnamate
-
-
(E)-2-fluoro-o-hydroxycinnamate
competitive
(E)-2-fluoro-p-hydroxycinnamate
(E)-2-Fluoro-p-hydroxycinnamic acid
-
-
(E)-2-fluorocinnamate
-
-
(E)-2-Fluorocinnamic acid
-
-
(E)-4-hydroxycinnamate
-
-
(E)-cinnamate
-
-
(E)-cinnamic acid
-
-
(E)-p-hydroxycinnamic acid
-
-
(p-Hydroxybenzylidene)malonate
-
-
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
(S,R)-3-phenyl-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
(Z)-2-fluoro-4-hydroxycinnamate
-
-
(Z)-2-fluoro-cinnamate
-
-
(Z)-2-fluorocinnamate
-
-
(Z)-2-Fluorocinnamic acid
-
-
(Z)-4-hydroxycinnamate
-
-
(Z)-cinnamate
-
-
(Z)-cinnamic acid
-
-
(Z)-Fluoro-p-hydroxycinnamic acid
-
-
(Z)-p-hydroxycinnamic acid
-
-
2,2-dimethylpropyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
2,2-dimethylpropyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
2,4,6-trimethylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
2,5-dibenzylidenecyclopentanone
-
-
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
-
2-Oxo-3-pentynoate
-
at pH 8.5, CCH2 is inactivated by 2-oxo-3-pentynoate due to the covalent modification of Pro-1
2-oxo-4-phenyl-3-butynoate
irreversible inactivation by covalent modifiaction of N-terminal proline residue via a Michael-addition of proline to C4 of the inhibitor
2-oxo-4-phenylbut-3-ynoic acid
-
inhibition mechanism, overview
2-piperidinoethyl isothiocyanate
-
-
2-propionylcyclohexanone
-
-
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
-
-
2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-N-(4-methoxyphenyl)acetamide
-
-
3,4-dihydroxycyclohexa-2,5-diene-1-carboxylic acid
-
-
3,4-dioxocyclohexa-1,5-diene-1-carboxylic acid
-
-
3,6-dihydroxy-1-methyl-5-oxo-3,5-dihydro-2H-indolium
-
-
3,6-dihydroxy-2-methyl-2,3-dihydro-5H-indol-5-one
-
-
3,6-dihydroxy-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
-
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
-
-
3-acetyl-7-hydroxy-2H-chromen-2-one
-
-
3-hydroxy-acetaminophen
-
-
3-hydroxybutyrate
-
-
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
-
-
4-coumaric acid
4-methoxyphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
4-tert-butylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylic acid
-
-
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
-
-
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
-
-
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
-
-
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
-
-
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
-
-
7-hydroxy-3-phenyl-2H-chromen-2-one
-
-
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
-
-
acetaminophen
acetoacetate
-
-
acetone
-
-
Acetylacetone
-
-
allyl isothiocyamate
-
-
AV1013
-
noncompetitive inhibitor of the p-hydroxyphenylpyruvate tautomerase activity of MIF
AV411
-
ibudilast, i.e. 3-isobutyryl-2-isopropylpyrazolo-[1,5-a]pyridine, noncompetitive inhibitor of the p-hydroxyphenylpyruvate tautomerase activity of MIF
AVP-13546
-
inhibits the tautomerase activity of MIF and reduces cytokine, including TNF-alpha, levels in vivo
-
Benzyl isothiocyanate
-
specific inhibition of MIF tautomerase activity is mediated by selective modification of the N-terminal proline
boldine
butyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
caffeate
-
-
caffeic acid
-
IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
carnosic acid
chlorogenic acid
Cinnamic acid
-
IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
coumarin
curcumin
cyclohexyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
cyclohexylmethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
-
-
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
inhibition mechanism, overview
ethyl acetoacetate
-
-
ethyl isothiocyanate
-
-
ethyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
eugenol
-
IC50 ketonase reaction 165.9 microM, pH 6.5, room temperatur
ferulic acid
folic acid
-
IC50 ketonase reaction 62.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 80.2 microM, pH 6.2, room temperatur
galangin
-
IC50 ketonase reaction 36.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 143.7 microM, pH 6.2, room temperatur
Ibuprofen
-
IC50 ketonase reaction 10334.3, pH 6.5, room temperatur, IC50 enolase reaction 109.6 microM, pH 6.2, room temperatur
iodoacetamide
-
-
isoeugenol
-
IC50 ketonase reaction 50.4 microM, pH 6.5, room temperatur, IC50 enolase reaction 129.0 microM, pH 6.2, room temperatur
methallyl isothiocyanate
-
-
methotrexate
-
IC50 ketonase reaction 15.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 63.7 microM, pH 6.2, room temperatur
methyl 6-hydroxy-2-methyl-5-oxo-3,5-dihydro-2H-indole-2-carboxylate
-
-
methyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
N-(2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
-
N-(3,4-dimethoxyphenyl)acetamide
-
-
N-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
-
N-(3-methyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide
-
-
N-(4-aminobutyl)-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
-
N-(4-hydroxy-3-methoxycyclohexa-2,5-dien-1-yl)acetamide
-
-
N-(4-hydroxy-3-methoxyphenyl)acetamide
-
-
N-acetyl-3-hydroxy-4-benzoquinone imine
-
-
N-acetyl-4-benzoquinone imine
-
-
N-cyclohexyl-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
-
-
o-coumaric acid
-
IC50 ketonase reaction 87.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 175.7 microM, pH 6.2, room temperatur
p-coumaric acid
-
IC50 ketonase reaction 18.1 microM, pH 6.5, room temperatur, IC50 enolase reaction 103.3 microM, pH 6.2, room temperatur
parthenolide
-
IC50 ketonase reaction 3624.1 microM, pH 6.5, room temperatur
phenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
Phenylbutazone
-
IC50 ketonase reaction 7126.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 376.6 microM, pH 6.2, room temperatur
phloretin
piroxicam
-
IC50 ketonase reaction 120.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 74.8 microM, pH 6.2, room temperatur
propan-2-yl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
propyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
Quinine
-
IC50 ketonase reaction 34.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 156.3 microM, pH 6.2, room temperatur
resveratrol
rosmarinic acid
scopoletin
-
IC50 ketonase reaction 133.8 microM, pH 6.5, room temperatur
tert-butyl [4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]carbamate
-
-
umbelliferone
VGX-1027
-
-
additional information
-