Information on EC 5.3.2.1 - Phenylpyruvate tautomerase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
5.3.2.1
-
RECOMMENDED NAME
GeneOntology No.
Phenylpyruvate tautomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
Keto-phenylpyruvate = enol-phenylpyruvate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular oxidoreduction
-
-
-
-
isomerization
-
-
-
-
tautomerization
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Phenylalanine metabolism
-
-
Tyrosine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
phenylpyruvate keto---enol-isomerase
Also acts on other arylpyruvates.
CAS REGISTRY NUMBER
COMMENTARY hide
9023-54-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Aerobacter sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(4-hydroxyphenyl)enolpyruvate
(4-hydroxyphenyl)pyruvate
show the reaction diagram
(4-Hydroxyphenyl)pyruvate
?
show the reaction diagram
-
-
-
-
-
(Diiodohydroxyphenyl)pyruvate
?
show the reaction diagram
-
keto-form
-
-
-
2-oxo-3-pentynoate
acetopyruvate + ?
show the reaction diagram
3-(3-hydroxyphenyl)pyruvate
2-hydroxy-3-(3-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
enol-form
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
4-(hydroxyphenyl)pyruvate
4-(hydroxyphenyl)pyruvate
show the reaction diagram
-
enol form
keto form
-
?
cis-3-chloroacrylate
malonate semialdehyde + HCl
show the reaction diagram
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
show the reaction diagram
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
keto-(4-hydroxyphenyl)pyruvate
enol-(4-hydroxyphenyl)pyruvate
show the reaction diagram
-
-
-
-
r
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
show the reaction diagram
keto-phenylpyruvate
enol-phenylpyruvate
show the reaction diagram
keto-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
-
-
r
phenylenolpyruvate
phenylpyruvate
show the reaction diagram
Phenylpyruvate
?
show the reaction diagram
-
-
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
trans-3-chloroacrylate
malonate semialdehyde + HCl
show the reaction diagram
-
the reaction is performed by CAAD
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(4-Hydroxyphenyl)pyruvate
?
show the reaction diagram
-
-
-
-
-
keto-(4-hydroxyphenyl)pyruvate
enol-(4-hydroxyphenyl)pyruvate
show the reaction diagram
-
-
-
-
r
keto-phenylpyruvate
enol-phenylpyruvate
show the reaction diagram
-
-
-
-
r
Phenylpyruvate
?
show the reaction diagram
-
-
-
-
-
additional information
?
-
INHIBITORS
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
-
competitive
(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
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.79 - 0.89
(4-hydroxyphenyl)enolpyruvate
0.072 - 2.4
(4-hydroxyphenyl)pyruvate
0.1
4-(hydroxyphenyl)pyruvate
-
mutant E16A, pH 6.8
0.152
cis-3-chloroacrylate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0.107 - 0.582
enol-(p-hydroxyphenyl)pyruvate
0.02 - 0.31
enol-phenylpyruvate
2.77
keto-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5
4.9
keto-phenylpyruvate
-
23C, pH 6.5
0.11 - 3.5
phenylenolpyruvate
6 - 8
phenylpyruvate
96
trans-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2 - 3.2
(4-hydroxyphenyl)enolpyruvate
0.052 - 1.89
(4-hydroxyphenyl)pyruvate
60
4-(hydroxyphenyl)pyruvate
Mus musculus
-
mutant E16A, pH 6.8
4.6
cis-3-chloroacrylate
Mycobacterium smegmatis
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0.8 - 160
enol-(p-hydroxyphenyl)pyruvate
0.6 - 660
enol-phenylpyruvate
0.03 - 120
keto-(p-hydroxyphenyl)pyruvate
285
keto-phenylpyruvate
Mus musculus
-
23C, pH 6.5
0.2 - 34
phenylenolpyruvate
0.45
phenylpyruvate
Sus scrofa
-
keto-form, kidney
0.0004
trans-3-chloroacrylate
Mycobacterium smegmatis
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.5 - 3.5
(4-hydroxyphenyl)enolpyruvate
1.6 - 30
cis-3-chloroacrylate
1.8 - 9.8
phenylenolpyruvate
4
trans-3-chloroacrylate
Mycobacterium smegmatis
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
41730
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0026
(E)-2-fluoro-o-hydroxycinnamate
-
23C, pH 6.5
0.013 - 0.04
(E)-2-fluoro-p-hydroxycinnamate
0.0241
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
pH and temperature not specified in the publication
0.234 - 0.375
4-coumaric acid
0.309
AV1013
-
pH and temperature not specified in the publication
0.0749
AV411
-
pH and temperature not specified in the publication
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0025
(2Z)-2-(2-methoxybenzylidene)cyclopentanone
Bos taurus
-
-
0.00079
(2Z)-2-(4-bromobenzylidene)cyclopentanone
Bos taurus
-
-
0.0031
(2Z)-2-(4-methoxybenzylidene)cyclohexanone
Bos taurus
-
-
0.0039
(2Z)-2-(4-methoxybenzylidene)cyclopentanone
Bos taurus
-
-
0.0056
(2Z)-2-(pyridin-2-ylmethylene)-3,4-dihydronaphthalen-1(2H)-one
Bos taurus
-
-
0.0062
(2Z)-2-benzylidenecyclopentanone
Bos taurus
-
22C, pH 6.5
0.0016
(2Z,5Z)-2,5-dibenzylidenecyclopentanone
Bos taurus
-
-
0.0062
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
Homo sapiens
-
-
0.0026
(E)-2-fluoro-4-hydroxycinnamate
Homo sapiens
-
-
0.073
(E)-2-fluoro-cinnamate
0.0015
(E)-4-hydroxycinnamate
Homo sapiens
-
-
0.007
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
Homo sapiens
-
-
0.013
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
Homo sapiens
-
-
0.48
(Z)-2-fluoro-4-hydroxycinnamate
Homo sapiens
-
-
2.33
(Z)-2-fluoro-cinnamate
0.21
(Z)-4-hydroxycinnamate
Homo sapiens
-
-
0.00161
2,5-dibenzylidenecyclopentanone
Homo sapiens
-
-
0.0016
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
Homo sapiens
-
-
0.0031
2-piperidinoethyl isothiocyanate
Homo sapiens
-
-
0.000038
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
Homo sapiens
-
-
0.0043
3-acetyl-7-hydroxy-2H-chromen-2-one
Homo sapiens
-
-
0.5
3-hydroxy-acetaminophen
Homo sapiens
-
-
0.0015
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
Homo sapiens
-
-
0.0029
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
Homo sapiens
-
-
0.00055
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
Homo sapiens
-
-
0.0021
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
Homo sapiens
-
-
0.0031
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
Homo sapiens
-
-
0.0005
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
Homo sapiens
-
-
0.00047
7-hydroxy-3-phenyl-2H-chromen-2-one
Homo sapiens
-
-
0.00028
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
Homo sapiens
-
-
0.001 - 10
acetaminophen
0.0037
allyl isothiocyamate
Homo sapiens
-
-
0.0013
AVP-13546
Homo sapiens
-
-
-
0.0008
Benzyl isothiocyanate
Homo sapiens
-
-
0.0057 - 0.0779
boldine
0.0005 - 0.002
caffeic acid
Bos taurus
-
IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
0.0155 - 0.1158
carnosic acid
0.0076 - 0.127
chlorogenic acid
0.0209 - 0.2296
Cinnamic acid
Bos taurus
-
IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
0.0888
coumarin
Bos taurus
-
IC50 ketonase reaction 88.8 microM, pH 6.5, room temperatur
0.0007 - 0.0122
curcumin
0.0058
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
Homo sapiens
-
-
0.0074
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
Homo sapiens
-
-
0.0111
ethyl isothiocyanate
Homo sapiens
-
-
0.1659
Eugenol
Bos taurus
-
IC50 ketonase reaction 165.9 microM, pH 6.5, room temperatur
0.0317 - 0.0853
ferulic acid
0.0627 - 0.0802
folic acid
0.0369 - 0.1437
galangin
0.1096 - 10.3343
Ibuprofen
0.0504 - 0.129
Isoeugenol
0.0014
methallyl isothiocyanate
Homo sapiens
-
-
0.0156 - 0.0637
methotrexate
0.0007
N-acetyl-3-hydroxy-4-benzoquinone imine
Homo sapiens
-
-
0.04
N-acetyl-4-benzoquinone imine
Homo sapiens
-
-
0.0878 - 0.1757
o-coumaric acid
0.0181 - 0.1033
p-coumaric acid
Bos taurus
-
IC50 ketonase reaction 18.1 microM, pH 6.5, room temperatur, IC50 enolase reaction 103.3 microM, pH 6.2, room temperatur
3.6241
parthenolide
Bos taurus
-
IC50 ketonase reaction 3624.1 microM, pH 6.5, room temperatur
0.3766 - 7.1267
Phenylbutazone
0.0048 - 0.0841
phloretin
0.0748 - 0.1209
piroxicam
0.0349 - 0.1563
Quinine
0.0019 - 0.028
resveratrol
0.0138 - 0.0656
rosmarinic acid
0.1338
scopoletin
Bos taurus
-
IC50 ketonase reaction 133.8 microM, pH 6.5, room temperatur
0.0026 - 0.0195
umbelliferone
Bos taurus
-
IC50 ketonase reaction 2.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 19.5 microM, pH 6.2, room temperatur
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.3
-
-
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2 - 8.2
-
no real optimum
6.2
-
-
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39000 - 44000
-
gel filtration, sucrose density gradient centrifugation
48000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterohexamer
homotrimer
trimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, crystal structure of Bm-MIF-2 at 1.8 A resolution reveals a trimeric assembly with an inner pore created by beta-stranded sheets from each subunit
hanging drop vapor diffusion method, crystal structure of the enzyme complexed with p-hydroxyphenylpyruvate
MIF is cocrystallized with the R-isomer of AV1013 alone and with the substrate enol-(p-hydroxyphenyl)pyruvate
-
crystal structure of a complex between enzyme and the competitive inhibitor (E)-2-fluoro-o-hydroxycinnamate determined to 1.8 A resolution
-
crystallization of the Y95F mutant enzyme by hanging drop vapor diffusion method, crystal structure of the enzyme with the competitive inhibitor (E)-2-fluoro-p-hydroxycinnamate bound at the active site and that of the protein complexed with the enol form of (p-hydroxyphenyl)pyruvate
-
crystals are soaked with inhibitor 2-oxo-4-phenyl-3-butynoate
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70
-
30 min, no loss of activity, 90 min, more the 70% loss of activity
72
-
5 min, no loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10C, stable for several months
-
-20C, 6 weeks, no loss of activity
-
4C, protein from homogenated tissue heated to 58C for 20 min, and subsequently salted out of the supernatant with ammonium sulfate to the final saturation of 80% can be stored six months without loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-Sepharose column chromatography
-
recombinant enzyme
-
recombinant MIF from Escherichia coli strain BL21(DE3) by anion exchange chromatography and gel filtration
-
simple method for purification based on size-exclusion chromatography on Toyopearl TSK polymer having a tendencey to adsorb the enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
-
expression in Escherichia coli
-
expression in Escherichia coli strain BL21(DE3)
-
expression in Escherichia coli, via pKK223-3 expression vector
-
wild-type and mutant enzymes P1G, P1A, Y95F and N97A, expression in Escherichia coli BL21
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
MIF expression is upregulated by cytokines, TNF-alpha and interleukin-I, and by bacterial endotoxins, such as lipopolysaccharides, and exotoxins
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
P1(A)M2
insertion abolishes activity
P1G
mutation substantially reduces the catalytic activity
E16A
-
kinetics similar to wild-type
K32A
-
15fold decrease in Ki-value for the competitive inhibitor, (E)-2-fluoro-p-hydroxycinnamate compared to wild-type enzyme, turnover number for enol-phenylpyruvate is 9% of that for the wild-type enzyme, turnover number for enol-(p-hydroxyphenyl)pyruvate is 11% of that for the wild-type enzyme, the ratio of turnover number and Km-value for enol-phenylpyruvate is 8% of that for the wild-type enzyme, the ratio of turnover number and KM-value for enol(p-hydroxyphenyl)pyruvate is 16% of the value for the wild-type enzyme
K32R
-
modest decrease in the stereoselectivity of the reaction and in the binding affinity of the competitive inhibitor, (E)-2-fluoro-p-hydroxycinnamate, turnover number for enol-phenylpyruvate is 47% of that for the wild-type enzyme, turnover number for enol-(p-hydroxyphenyl)pyruvate is 110% of that for the wild-type enzyme, the ratio of turnover number and Km-value for enol-phenylpyruvate or enol(p-hydroxyphenyl)pyruvate is about 70% of the value for the wild-type enzyme
N97A
-
the ratio of turnover number to Km-value for enol-phenylpyruvate is 21.3fold higher than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 1.5fold lower than that of the wild-type enzyme, 5fold increase in Ki-value for (E)-2-fluoro-p-hydroxycinnamate compared to the wild-type enzyme
P1A
-
the ratio of turnover number to Km-value for enol-phenylpyruvate is 232fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 114fold lower than that of the wild-type enzyme
P1F
-
mutant enzyme is completely inactive
P1G
-
the ratio of turnover number to Km-value for enol-phenylpyruvate is 232fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 143fold lower than that of the wild-type enzyme
P1S
-
mutant enzyme is nearly inactive
Y95F
-
the ratio of turnover number to Km-value for enol-phenylpyruvate is 1.3fold lower than that of the wild-type enzyme, the ratio of turnover number to Km-value for enol-(p-hydroxyphenyl)pyruvate is 1.5fold higher than that of the wild-type enzyme
E52Q
-
mutation in alpha-subunit, 1.6fold increase in ratio of kcat to Km value
P1A
-
mutation in beta-subunit, 8fold decrease in ratio of kcat to Km value
R11A
-
mutation in alpha-subunit, 15fold decrease in ratio of kcat to Km value
R8A
-
mutation in alpha-subunit, 19fold decrease in ratio of kcat to Km value
E52Q
-
mutation in alpha-subunit, 1.6fold increase in ratio of kcat to Km value
-
P1A
-
mutation in beta-subunit, 8fold decrease in ratio of kcat to Km value
-
R11A
-
mutation in alpha-subunit, 15fold decrease in ratio of kcat to Km value
-
R8A
-
mutation in alpha-subunit, 19fold decrease in ratio of kcat to Km value
-
additional information
-
modification of Pro1, e.g. via isothiocyanate inhibitors, alters the tertiary, but not the secondary or quaternary, structure of the trimer without affecting its thermodynamic stability, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
the tautomerase activity of MIF is a target for inhibitor development, overview