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(4-hydroxyphenyl)enolpyruvate
(4-hydroxyphenyl)pyruvate
(4-Hydroxyphenyl)pyruvate
?
-
Substrates: -
Products: -
?
(Diiodohydroxyphenyl)pyruvate
?
-
Substrates: keto-form
Products: -
?
2-oxo-3-pentynoate
acetopyruvate + ?
3-(3-hydroxyphenyl)pyruvate
2-hydroxy-3-(3-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: enol-form
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
4-(hydroxyphenyl)pyruvate
4-(hydroxyphenyl)pyruvate
Substrates: enol form
Products: keto form
?
cis-3-chloroacrylate
malonate semialdehyde + HCl
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
enol-phenylpyruvate
keto-phenylpyruvate
keto-(4-hydroxyphenyl)pyruvate
enol-(4-hydroxyphenyl)pyruvate
-
Substrates: -
Products: -
r
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
keto-phenylpyruvate
enol-phenylpyruvate
phenylenolpyruvate
phenylpyruvate
Phenylpyruvate
?
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
trans-3-chloroacrylate
malonate semialdehyde + HCl
-
Substrates: the reaction is performed by CAAD
Products: -
?
additional information
?
-
(4-hydroxyphenyl)enolpyruvate
(4-hydroxyphenyl)pyruvate
-
Substrates: -
Products: -
?
(4-hydroxyphenyl)enolpyruvate
(4-hydroxyphenyl)pyruvate
-
Substrates: -
Products: -
?
2-oxo-3-pentynoate
acetopyruvate + ?
-
Substrates: at pH 6.5, CCH2 exhibits hydratase activity and converts 2-oxo-3-pentynoate to acetopyruvate
Products: -
?
2-oxo-3-pentynoate
acetopyruvate + ?
-
Substrates: at pH 6.5, CCH2 exhibits hydratase activity and converts 2-oxo-3-pentynoate to acetopyruvate
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: -
?
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
-
Substrates: keto-form
Products: enol-form
?
cis-3-chloroacrylate
malonate semialdehyde + HCl
-
Substrates: the reaction is performed by cis-CAAD
Products: -
?
cis-3-chloroacrylate
malonate semialdehyde + HCl
-
Substrates: the reaction is performed by cis-CAAD
Products: -
?
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
-
Substrates: -
Products: -
?
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
-
Substrates: -
Products: -
r
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
Substrates: -
Products: -
r
enol-phenylpyruvate
keto-phenylpyruvate
-
Substrates: -
Products: -
r
enol-phenylpyruvate
keto-phenylpyruvate
Substrates: -
Products: -
?
enol-phenylpyruvate
keto-phenylpyruvate
Substrates: -
Products: -
r
enol-phenylpyruvate
keto-phenylpyruvate
-
Substrates: -
Products: reaction is stereoselective, generating the (3R) isomer of [3-D]phenylpyruvate in D2O in a ratio of 6.6:1
?
enol-phenylpyruvate
keto-phenylpyruvate
-
Substrates: reaction is stereoselective, generating the 3S isomer of [3-D]phenylpyruvate in a 18:1 ratio in D2O
Products: -
?
enol-phenylpyruvate
keto-phenylpyruvate
-
Substrates: reaction is stereoselective, generating the 3S isomer of [3-D]phenylpyruvate in a 18:1 ratio in D2O
Products: -
?
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
Substrates: the substrate interacts with Pro1, Lys32 and Ile64 from one subunit and Tyr95 and Asn97 from an adjacent subunit
Products: -
?
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
Substrates: -
Products: -
r
keto-phenylpyruvate
enol-phenylpyruvate
-
Substrates: -
Products: -
r
keto-phenylpyruvate
enol-phenylpyruvate
-
Substrates: -
Products: -
r
keto-phenylpyruvate
enol-phenylpyruvate
Substrates: -
Products: -
r
phenylenolpyruvate
phenylpyruvate
-
Substrates: -
Products: -
?
phenylenolpyruvate
phenylpyruvate
-
Substrates: -
Products: -
?
phenylenolpyruvate
phenylpyruvate
-
Substrates: -
Products: -
?
phenylenolpyruvate
phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: r
Products: enol-form
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: converts the enol-form to the keto-form by incorporating a solvent proton into the pro-R position, in the reverse reaction the same pro-R proton is abstracted
Products: enol-form
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: keto-form
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: keto-form
Products: enol-form
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: keto-form
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: -
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: r
Products: -
?
Phenylpyruvate
Phenylpyruvate
-
Substrates: keto-form
Products: -
?
additional information
?
-
Substrates: the enzyme is chemotactic for human monocytes and activates them to produce IL-8, TNF-alpha and endogenous MIF
Products: -
?
additional information
?
-
-
Substrates: the enzyme is chemotactic for human monocytes and activates them to produce IL-8, TNF-alpha and endogenous MIF
Products: -
?
additional information
?
-
Substrates: important immunoregulatory molecule with a unique ability to suppress the anti-inflammatory effects of glucocorticoids
Products: -
?
additional information
?
-
-
Substrates: MIF is a homotrimeric multifunctional proinflammatory cytokine. It also shows dopachrome tautomerase activity. Binding of MIF to its receptor, CD74, overview
Products: -
?
additional information
?
-
-
Substrates: 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
Products: -
?
additional information
?
-
-
Substrates: the N-terminal Pro is essential for the tautomerase activity of MIF
Products: -
?
additional information
?
-
-
Substrates: the enzymatic activity of macrophage migration inhibitory factor does not play a role in its migration inhibiting properties. Macrophage migration inhibitory factor is an inhibitor of the random migration of monocytes and macrophages and has since been proposed to have a number of immune and catalytic functions, macrophage migration inhibitory factor is an inhibitor of monocyte chemoattractant protein 1-induced chemotaxis of human peripheral blood monocytes
Products: -
?
additional information
?
-
-
Substrates: CCH2 functions as an efficient PPT and exhibits low-level promiscuous dehalogenase activity, processing both cis- and trans-3-chloroacrylic acid
Products: -
?
additional information
?
-
-
Substrates: CCH2 functions as an efficient PPT and exhibits low-level promiscuous dehalogenase activity, processing both cis- and trans-3-chloroacrylic acid
Products: -
?
additional information
?
-
-
Substrates: role in the biosynthesis of thyroxine
Products: -
?
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(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)-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)-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-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
-
-
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
-
-
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
butyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
caffeic acid
-
IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
Cinnamic acid
-
IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
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 [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
eugenol
-
IC50 ketonase reaction 165.9 microM, pH 6.5, room temperatur
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
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
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
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
-
-
(E)-2-fluoro-p-hydroxycinnamate
-
competitive
(E)-2-fluoro-p-hydroxycinnamate
competitive
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
i.e. ISO-I
(S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
4-coumaric acid
-
-
acetaminophen
-
IC50 ketonase reaction 1.0 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.6 microM, pH 6.2, room temperatur
boldine
-
IC50 ketonase reaction 5.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 77.9 microM, pH 6.2, room temperatur
carnosic acid
-
IC50 ketonase reaction 15.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 115.8 microM, pH 6.2, room temperatur
chlorogenic acid
-
IC50 ketonase reaction 7.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 127.0 microM, pH 6.2, room temperatur
coumarin
-
IC50 ketonase reaction 88.8 microM, pH 6.5, room temperatur
curcumin
-
IC50 ketonase reaction 0.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 12.2 microM, pH 6.2, room temperatur
ferulic acid
-
IC50 ketonase reaction 31.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 85.3 microM, pH 6.2, room temperatur
phloretin
-
IC50 ketonase reaction 4.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 84.1 microM, pH 6.2, room temperatur
resveratrol
-
IC50 ketonase reaction 1.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 28.0 microM, pH 6.2, room temperatur
rosmarinic acid
-
IC50 ketonase reaction 13.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 65.6 microM, pH 6.2, room temperatur
umbelliferone
-
IC50 ketonase reaction 2.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 19.5 microM, pH 6.2, room temperatur
additional information
-
50% inhibition could not be attained: estragol, gentisic acid, tropolone
-
additional information
-
design and synthesis of irreversible isothiocyanate-based inhibitors of MIF, inhibitory potencies and inhibition mechanism, overview
-
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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 22°C
0.107 - 0.582
enol-(p-hydroxyphenyl)pyruvate
0.02 - 0.31
enol-phenylpyruvate
2.77
keto-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5
4.9
keto-phenylpyruvate
23°C, pH 6.5
0.11 - 3.5
phenylenolpyruvate
96
trans-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22°C
0.79
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.89
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.072
(4-hydroxyphenyl)pyruvate
-
enol-form, kidney
1.2
(4-hydroxyphenyl)pyruvate
-
thyroid gland
2.2
(4-hydroxyphenyl)pyruvate
-
keto-form, kidney
2.4
(4-hydroxyphenyl)pyruvate
-
-
0.107
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme Y95F
0.11
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme Y97A
0.14
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, mutant enzyme K32A
0.143
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme P1G
0.17
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5
0.2
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, wild-type enzyme
0.2
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, wild-type enzyme
0.35
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, mutant enzyme K32R
0.582
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme P1A
0.02
enol-phenylpyruvate
-
pH 9.0
0.031
enol-phenylpyruvate
-
pH 6.8
0.061
enol-phenylpyruvate
-
wild-type, pH 9.0
0.1
enol-phenylpyruvate
-
23°C, pH 6.5, mutant enzyme K32R
0.107
enol-phenylpyruvate
23°C, mutant enzyme P1G
0.112
enol-phenylpyruvate
23°C, mutant enzyme Y95F
0.113
enol-phenylpyruvate
-
mutant E52Q, pH 9.0
0.13
enol-phenylpyruvate
23°C, pH 6.5
0.15
enol-phenylpyruvate
-
23°C, pH 6.5, wild-type enzyme
0.16
enol-phenylpyruvate
mutant E16A, pH 6.8
0.18
enol-phenylpyruvate
23°C, mutant enzyme N97A
0.18
enol-phenylpyruvate
-
23°C, pH 6.5, mutant enzyme K32A
0.303
enol-phenylpyruvate
23°C, mutant enzyme P1A
0.31
enol-phenylpyruvate
23°C, wild-type enzyme
0.11
phenylenolpyruvate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.25
phenylenolpyruvate
-
mutant enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
3.5
phenylenolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
6
phenylpyruvate
-
-
6.1
phenylpyruvate
-
keto-form, kidney
8
phenylpyruvate
-
thyroid gland
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.2 - 3.2
(4-hydroxyphenyl)enolpyruvate
0.052 - 1.89
(4-hydroxyphenyl)pyruvate
60
4-(hydroxyphenyl)pyruvate
mutant E16A, pH 6.8
4.6
cis-3-chloroacrylate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.8 - 160
enol-(p-hydroxyphenyl)pyruvate
0.6 - 660
enol-phenylpyruvate
0.03 - 120
keto-(p-hydroxyphenyl)pyruvate
285
keto-phenylpyruvate
23°C, pH 6.5
0.2 - 34
phenylenolpyruvate
0.45
phenylpyruvate
-
keto-form, kidney
0.0004
trans-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22°C
0.2
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
3.2
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.052
(4-hydroxyphenyl)pyruvate
-
enol-form, kidney
1.89
(4-hydroxyphenyl)pyruvate
-
keto-form, kidney
0.8
enol-(p-hydroxyphenyl)pyruvate
23°C, mutant enzyme P1G
4.1
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme P1A
15
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, mutant enzyme K32A
58
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme N97A
126
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, mutant enzyme Y95F
140
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, wild-type enzyme
160
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5
160
enol-(p-hydroxyphenyl)pyruvate
-
23°C, pH 6.5, mutant enzyme K32R
160
enol-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5, wild-type enzyme
0.6
enol-phenylpyruvate
23°C, mutant enzyme P1G
1.4
enol-phenylpyruvate
-
wild-type, pH 9.0
1.7
enol-phenylpyruvate
23°C, mutant enzyme P1A
4.1
enol-phenylpyruvate
-
mutant E52Q, pH 9.0
30
enol-phenylpyruvate
-
23°C, pH 6.5, mutant enzyme K32A
33
enol-phenylpyruvate
-
pH 9.0
38
enol-phenylpyruvate
-
pH 6.8
109
enol-phenylpyruvate
23°C, mutant enzyme Y95F
150
enol-phenylpyruvate
-
23°C, pH 6.5, mutant enzyme K32R
200
enol-phenylpyruvate
mutant E16A, pH 6.8
290
enol-phenylpyruvate
23°C, pH 6.5
320
enol-phenylpyruvate
-
23°C, pH 6.5, wild-type enzyme
410
enol-phenylpyruvate
23°C, wild-type enzyme
660
enol-phenylpyruvate
23°C, mutant enzyme N97A
0.03
keto-(p-hydroxyphenyl)pyruvate
25°C, pH 6.0, mutant enzyme P1(A)M2
0.93
keto-(p-hydroxyphenyl)pyruvate
25°C, pH 6.0, mutant enzyme P1G
2.7
keto-(p-hydroxyphenyl)pyruvate
25°C, pH 6.0, wild-type enzyme
6.08
keto-(p-hydroxyphenyl)pyruvate
25°C, pH 6.0, mutant enzyme P1G
120
keto-(p-hydroxyphenyl)pyruvate
23°C, pH 6.5
0.2
phenylenolpyruvate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
0.8
phenylenolpyruvate
-
mutant enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
34
phenylenolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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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
-
22°C, 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
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
-
-
0.0037
allyl isothiocyamate
Homo sapiens
-
-
0.0013
AVP-13546
Homo sapiens
-
-
-
0.0008
Benzyl isothiocyanate
Homo sapiens
-
-
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
0.0058
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
0.1096 - 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
0.0019 - 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
0.001
acetaminophen
Bos taurus
-
IC50 ketonase reaction 1.0 microM, pH 6.5, room temperatur
0.0026
acetaminophen
Bos taurus
-
IC50 enolase reaction 2.6 microM, pH 6.2, room temperatur
10
acetaminophen
Homo sapiens
-
-
0.0057
boldine
Bos taurus
-
IC50 ketonase reaction 5.7 microM, pH 6.5, room temperatur
0.0779
boldine
Bos taurus
-
IC50 enolase reaction 77.9 microM, pH 6.2, room temperatur
0.0155
carnosic acid
Bos taurus
-
IC50 ketonase reaction 15.5 microM, pH 6.5, room temperatur
0.1158
carnosic acid
Bos taurus
-
IC50 enolase reaction 115.8 microM, pH 6.2, room temperatur
0.0076
chlorogenic acid
Bos taurus
-
IC50 ketonase reaction 7.6 microM, pH 6.5, room temperatur
0.127
chlorogenic acid
Bos taurus
-
IC50 enolase reaction 127.0 microM, pH 6.2, room temperatur
0.0007
curcumin
Bos taurus
-
IC50 ketonase reaction 0.7 microM, pH 6.5, room temperatur
0.0122
curcumin
Bos taurus
-
IC50 enolase reaction 12.2 microM, pH 6.2, room temperatur
0.0317
ferulic acid
Bos taurus
-
IC50 ketonase reaction 31.7 microM, pH 6.5, room temperatur
0.0853
ferulic acid
Bos taurus
-
IC50 enolase reaction 85.3 microM, pH 6.2, room temperatur
0.0627
folic acid
Bos taurus
-
IC50 ketonase reaction 62.7 microM, pH 6.5, room temperatur
0.0802
folic acid
Bos taurus
-
IC50 enolase reaction 80.2 microM, pH 6.2, room temperatur
0.0802
folic acid
Bos taurus
-
80.2 microM
0.0369
galangin
Bos taurus
-
IC50 ketonase reaction 36.9 microM, pH 6.5, room temperatur
0.1437
galangin
Bos taurus
-
IC50 enolase reaction 143.7 microM, pH 6.2, room temperatur
0.1096
Ibuprofen
Bos taurus
-
IC50 enolase reaction 109.6 microM, pH 6.2, room temperatur
10.3343
Ibuprofen
Bos taurus
-
IC50 ketonase reaction 10334.3 microM, pH 6.5, room temperatur
0.0504
isoeugenol
Bos taurus
-
IC50 ketonase reaction 50.4 microM, pH 6.5, room temperatur
0.129
isoeugenol
Bos taurus
-
IC50 enolase reaction 129.0 microM, pH 6.2, room temperatur
0.0156
methotrexate
Bos taurus
-
IC50 ketonase reaction 15.6 microM, pH 6.5, room temperatur
0.0637
methotrexate
Bos taurus
-
IC50 enolase reaction 63.7 microM, pH 6.2, room temperatur
0.0878
o-coumaric acid
Bos taurus
-
IC50 ketonase reaction 87.8 microM, pH 6.5, room temperatur
0.1757
o-coumaric acid
Bos taurus
-
IC50 enolase reaction 175.7 microM, pH 6.2, room temperatur
0.3766
Phenylbutazone
Bos taurus
-
IC50 enolase reaction 376.6 microM, pH 6.2, room temperatur
7.1267
Phenylbutazone
Bos taurus
-
IC50 ketonase reaction 7126.7 microM, pH 6.5, room temperatur
0.0048
phloretin
Bos taurus
-
IC50 ketonase reaction 4.8 microM, pH 6.5, room temperatur
0.0841
phloretin
Bos taurus
-
IC50 enolase reaction 84.1 microM, pH 6.2, room temperatur
0.0748
piroxicam
Bos taurus
-
IC50 enolase reaction 74.8 microM, pH 6.2, room temperatur
0.1209
piroxicam
Bos taurus
-
IC50 ketonase reaction 120.9 microM, pH 6.5, room temperatur
0.0349
Quinine
Bos taurus
-
IC50 ketonase reaction 34.9 microM, pH 6.5, room temperatur
0.1563
Quinine
Bos taurus
-
IC50 enolase reaction 156.3 microM, pH 6.2, room temperatur
0.0019
resveratrol
Bos taurus
-
IC50 ketonase reaction 1.9 microM, pH 6.5, room temperatur
0.028
resveratrol
Bos taurus
-
IC50 enolase reaction 28.0 microM, pH 6.2, room temperatur
0.0138
rosmarinic acid
Bos taurus
-
IC50 ketonase reaction 13.8 microM, pH 6.5, room temperatur
0.0656
rosmarinic acid
Bos taurus
-
IC50 enolase reaction 65.6 microM, pH 6.2, room temperatur
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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
P1A
-
for phenylenolpyruvate, the P1A mutant shows a 41fold decrease in kcat and a 14fold decrease in Km, resulting in an about 3fold decrease in kcat/Km. For (4-hydroxyphenyl)enolpyruvate, the P1A mutant shows a 16fold decrease in kcat, whereas the Km is not significantly affected, resulting in a 16fold decrease in kcat/Km. The P1A mutant has no detectable dehalogenase activity toward cis-3-chloroacrylate and trans-3-chloroacrylate, and no detectable activity toward 2-oxo-3-pentynoate (at pH 7.3)
P1A
-
for phenylenolpyruvate, the P1A mutant shows a 41fold decrease in kcat and a 14fold decrease in Km, resulting in an about 3fold decrease in kcat/Km. For (4-hydroxyphenyl)enolpyruvate, the P1A mutant shows a 16fold decrease in kcat, whereas the Km is not significantly affected, resulting in a 16fold decrease in kcat/Km. The P1A mutant has no detectable dehalogenase activity toward cis-3-chloroacrylate and trans-3-chloroacrylate, and no detectable activity toward 2-oxo-3-pentynoate (at pH 7.3)
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Knox, W.E.; Pitt, B.M.
Enzymic catalysis of the keto-enol tautomerization of phenylpyruvic acids
J. Biol. Chem.
225
675-688
1957
Bos taurus, Canis lupus familiaris, Cavia porcellus, Oryctolagus cuniculus, Equus caballus, Neurospora sp., no activity in Aerobacter sp., Pseudomonas sp., Rattus norvegicus, Sus scrofa
brenda
Blasi, F.; Fragomele, F.; Covelli, I.
Thyroidal phenylpyruvate tautomerase
J. Biol. Chem.
244
4864-4870
1969
Sus scrofa
brenda
Knox, W.E.
p-Hydroxyphenylpyruvate enol-keto tautomerase
Methods Enzymol.
2
289-292
1955
Sus scrofa
-
brenda
Retey, J.; Bartl, K.; Ripp, E.; Hull, W.E.
Stereospecificity of phenylpyruvate tautomerase. A convenient method for the preparation of chirally labelled phenylpyruvates
Eur. J. Biochem.
72
251-257
1977
Bos taurus
brenda
Pirrung, M.C.; Chen, J.; Rowley, E.G.; McPhall, A.T.
Mechanistic and stereochemical study of phenylpyruvate tautomerase
J. Am. Chem. Soc.
115
7103-7110
1993
Sus scrofa
-
brenda
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
brenda
Hermanowski-Vosatka, A.; Mundt, S.S.; Ayala, J.M.; Goyal, S.; Hanlon, W.A.; Czerwinski, R.M.; Wright, S.D.; Whitman, C.P.
Enzymatically inactive macrophage migration inhibitory factor inhibits monocyte chemotaxis and random migration
Biochemistry
38
12841-12849
1999
Mus musculus
brenda
Johnson, W.H., Jr.; Czerwinski, R.M.; Stamps, S.L.; Whitman, C.P.
A kinetic and stereochemical investigation of the role of lysine-32 in the phenylpyruvate tautomerase activity catalyzed by macrophage migration inhibitory factor
Biochemistry
38
16024-16033
1999
Mus musculus
brenda
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)
brenda
Taylor, A.B.; Johnson, W.H., Jr.; Czerwinski, R.M.; Li, H.S.; Hackert, M.L.; Whitman, C.P.
Crystal structure of macrophage migration inhibitory factor complexed with (E)-2-fluoro-p-hydroxycinnamate at 1.8 A resolution: implications for enzymatic catalysis and inhibition
Biochemistry
38
7444-7452
1999
Mus musculus (P34884), Mus musculus
brenda
Stamps, S.L.; Taylor, A.B.; Wang, S.C.; Hackert, M.L.; Whitman, C.P.
Mechanism of the phenylpyruvate tautomerase activity of macrophage migration inhibitory factor: properties of the P1G, P1A, Y95F, and N97A mutants
Biochemistry
39
9671-9678
2000
Mus musculus (P34884)
brenda
Zang, X.; Taylor, P.; Wang, J.M.; Meyer, D.J.; Scott, A.L.; Walkinshaw, M.D.; Maizels, R.M.
Homologues of human macrophage migration inhibitory factor from a parasitic nematode. Gene cloning, protein activity, and crystal structure
J. Biol. Chem.
277
44261-44267
2002
Brugia malayi (Q9NAS2), Brugia malayi
brenda
Molnar, V.; Garai, J.
Plant-derived anti-inflammatory compounds affect MIF tautomerase activity
Int. Immunopharmacol.
5
849-856
2005
Bos taurus
brenda
Poelarends, G.J.; Johnson, W.H.; Serrano, H.; Whitman, C.P.
Phenylpyruvate tautomerase activity of trans-3-chloroacrylic acid dehalogenase: evidence for an enol intermediate in the dehalogenase reaction?
Biochemistry
46
9596-9604
2007
Mus musculus, Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
brenda
Cherepkova, O.A.; Lyutova, E.M.; Gurvits, B.Y.
Macrophage migration inhibitory factor: isolation from bovine brain
Biochemistry (Moscow)
71
73-78
2006
Bos taurus
brenda
Golubkov, P.A.; Johnson, W.H.; Czerwinski, R.M.; Person, M.D.; Wang, S.C.; Whitman, C.P.; Hackert, M.L.
Inactivation of the phenylpyruvate tautomerase activity of macrophage migration inhibitory factor by 2-oxo-4-phenyl-3-butynoate
Bioorg. Chem.
34
183-199
2006
Mus musculus (P34884)
brenda
Garai, J.; Molnar, V.; Eros, D.; Orfi, L.; Lorand, T.
MIF tautomerase inhibitor potency of alpha,beta-unsaturated cyclic ketones
Int. Immunopharmacol.
7
1741-1746
2007
Bos taurus
brenda
Poelarends, G.J.; Veetil, V.P.; Whitman, C.P.
The chemical versatility of the beta-alpha-beta fold: catalytic promiscuity and divergent evolution in the tautomerase superfamily
Cell. Mol. Life Sci.
65
3606-3618
2008
Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
brenda
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
brenda
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
brenda
Baas, B.J.; Zandvoort, E.; Wasiel, A.A.; Quax, W.J.; Poelarends, G.J.
Characterization of a newly identified mycobacterial tautomerase with promiscuous dehalogenase and hydratase activities reveals a functional link to a recently diverged cis-3-chloroacrylic acid dehalogenase
Biochemistry
50
2889-2899
2011
Mycolicibacterium smegmatis, Mycolicibacterium smegmatis mc(2)155
brenda
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
brenda