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Information on EC 5.3.2.1 - phenylpyruvate tautomerase and Organism(s) Homo sapiens and UniProt Accession P14174

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EC Tree
     5 Isomerases
         5.3 Intramolecular oxidoreductases
             5.3.2 Interconverting keto- and enol-groups
                5.3.2.1 phenylpyruvate tautomerase
IUBMB Comments
Also acts on other arylpyruvates.
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Select one or more organisms in this record: ?
This record set is specific for:
Homo sapiens
UNIPROT: P14174
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
macrophage migration inhibitory factor, cis-caad, mif tautomerase, trans-3-chloroacrylic acid dehalogenase, cis-3-chloroacrylic acid dehalogenase, phenylpyruvate tautomerase, phenylpyruvate keto-enol tautomerase, macrophage migration inhibitory factor tautomerase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Macrophage migration inhibitory factor
macrophage migration inhibitory factor tautomerase
-
-
MIF tautomerase
-
-
Phenylpyruvate keto-enol tautomerase
-
-
-
-
Phenylpyruvic keto-enol isomerase
-
-
-
-
Tautomerase, phenylpyruvate
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
isomerization
-
-
-
-
intramolecular oxidoreduction
-
-
-
-
tautomerization
-
-
-
-
PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
phenylpyruvate keto---enol-isomerase
Also acts on other arylpyruvates.
CAS REGISTRY NUMBER
COMMENTARY hide
9023-54-5
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
show the reaction diagram
the substrate interacts with Pro1, Lys32 and Ile64 from one subunit and Tyr95 and Asn97 from an adjacent subunit
-
?
(4-Hydroxyphenyl)pyruvate
?
show the reaction diagram
-
-
-
-
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
?
enol-(p-hydroxyphenyl)pyruvate
keto-(p-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
-
-
-
-
?
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
keto-form
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
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
?
-
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
-
-
(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-fluorocinnamate
-
-
(E)-4-hydroxycinnamate
-
-
(E)-cinnamate
-
-
(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)-4-hydroxycinnamate
-
-
(Z)-cinnamate
-
-
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-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
-
-
carnosic acid
-
-
chlorogenic acid
-
-
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
-
-
ferulic acid
-
-
iodoacetamide
-
-
methallyl isothiocyanate
-
-
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
-
-
phenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
phloretin
-
-
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
-
-
resveratrol
-
-
rosmarinic acid
-
-
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
2.4
(4-hydroxyphenyl)pyruvate
-
-
6
phenylpyruvate
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.03 - 6.08
keto-(p-hydroxyphenyl)pyruvate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0241
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
pH and temperature not specified in the publication
0.309
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
0.0062
(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
Homo sapiens
-
-
0.073
(E)-2-fluorocinnamate
Homo sapiens
-
-
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
Homo sapiens
-
-
2.33
(Z)-2-fluorocinnamate
Homo sapiens
-
-
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
-
-
10
acetaminophen
Homo sapiens
-
-
0.0037
allyl isothiocyamate
Homo sapiens
-
-
0.0013
AVP-13546
Homo sapiens
-
-
-
0.0008
Benzyl isothiocyanate
Homo sapiens
-
-
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
-
-
0.0014
methallyl isothiocyanate
Homo sapiens
-
-
0.0007
N-acetyl-3-hydroxy-4-benzoquinone imine
Homo sapiens
-
-
0.04
N-acetyl-4-benzoquinone imine
Homo sapiens
-
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
Uniprot
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
-
corticotrop cells
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
MIF_HUMAN
115
0
12476
Swiss-Prot
other Location (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
12345
x * 12345, wild-type enzyme, mass spectrometry
12000
-
x * 12000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 12345, wild-type enzyme, mass spectrometry
?
-
x * 12000, SDS-PAGE
trimer
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
P1(A)M2
insertion abolishes activity
P1G
mutation substantially reduces the catalytic activity
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant MIF from Escherichia coli strain BL21(DE3) by anion exchange chromatography and gel filtration
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli strain BL21(DE3)
-
expression in Escherichia coli, via pKK223-3 expression vector
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
MIF expression is upregulated by cytokines, TNF-alpha and interleukin-I, and by bacterial endotoxins, such as lipopolysaccharides, and exotoxins
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
the tautomerase activity of MIF is a target for inhibitor development, overview
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Rosengarten, E.; Aman, P.; Thelin, S.; Hansson, C.; Ahlfors, S.; Bjoerk, P.; Jacobson, L.; Rorsman, H.
The macrophage inhibitory factor MIF is a phenylpyruvate tautomerase
FEBS Lett.
417
85-88
1997
Bos taurus, Homo sapiens
Manually annotated by BRENDA team
Lubetsky, J.B.; Swope, M.; Dealwis, C.; Blake, P.; Lolis, E.
Pro-1 of macrophage migration inhibitory factor functions as a catalytic base in the phenylpyruvate tautomerase activity
Biochemistry
38
7346-7354
1999
Homo sapiens (P14174)
Manually annotated by BRENDA team
Ouertatani-Sakouhi, H.; El-Turk, F.; Fauvet, B.; Roger, T.; Le Roy, D.; Karpinar, D.P.; Leng, L.; Bucala, R.; Zweckstetter, M.; Calandra, T.; Lashuel, H.A.
A new class of isothiocyanate-based irreversible inhibitors of macrophage migration inhibitory factor
Biochemistry
48
9858-9870
2009
Homo sapiens
Manually annotated by BRENDA team
Garai, J.; Lorand, T.
Macrophage migration inhibitory factor (MIF) tautomerase inhibitors as potential novel anti-inflammatory agents: current developments
Curr. Med. Chem.
16
1091-1114
2009
Homo sapiens
Manually annotated by BRENDA team
Cho, Y.; Crichlow, G.V.; Vermeire, J.J.; Leng, L.; Du, X.; Hodsdon, M.E.; Bucala, R.; Cappello, M.; Gross, M.; Gaeta, F.; Johnson, K.; Lolis, E.J.
Allosteric inhibition of macrophage migration inhibitory factor revealed by ibudilast
Proc. Natl. Acad. Sci. USA
107
11313-11318
2010
Homo sapiens
Manually annotated by BRENDA team