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
5.3.2.1
-
RECOMMENDED NAME
GeneOntology No.
Phenylpyruvate tautomerase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Keto-phenylpyruvate = enol-phenylpyruvate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
intramolecular oxidoreduction
-
-
-
-
isomerization
-
-
-
-
tautomerization
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Phenylalanine metabolism
-
Tyrosine metabolism
-
SYSTEMATIC NAME
IUBMB Comments
phenylpyruvate keto---enol-isomerase
Also acts on other arylpyruvates.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
CaaD
Mycobacterium smegmatis MC2 155
-
-
-
CaaD
-
CaaD (trans-3-chloroacrylic acid dehalogenase) exhibits a robust phenylpyruvate tautomerase activity
CaaD
Pseudomonas pavonaceae 170
-
; CaaD (trans-3-chloroacrylic acid dehalogenase) exhibits a robust phenylpyruvate tautomerase activity
-
cis-3-chloroacrylic acid dehalogenase
-
-
cis-3-chloroacrylic acid dehalogenase
Mycobacterium smegmatis MC2 155
-
-
-
cis-CaaD
Mycobacterium smegmatis MC2 155
-
-
-
Macrophage migration inhibitory factor
-
-
-
-
Macrophage migration inhibitory factor
-
-
Macrophage migration inhibitory factor
-
-
Macrophage migration inhibitory factor
-
-
macrophage migration inhibitory factor tautomerase
-
-
MIF
-
-
-
-
MIF
-
-
MIF tautomerase
-
-
phenyl(enol)pyruvate tautomerase
-
-
phenyl(enol)pyruvate tautomerase
Mycobacterium smegmatis MC2 155
-
-
-
Phenylpyruvate keto-enol tautomerase
-
-
-
-
Phenylpyruvic keto-enol isomerase
-
-
-
-
PPT
Mycobacterium smegmatis MC2 155
-
-
-
PPT
Pseudomonas pavonaceae 170
-
-
-
Tautomerase, phenylpyruvate
-
-
-
-
trans-3-chloroacrylic acid dehalogenase
-
-
CAS REGISTRY NUMBER
COMMENTARY
9023-54-5
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
macrophage migration inhibitory factor
-
-
Manually annotated by BRENDA team
macrophage migration inhibitory factor MIF
-
-
Manually annotated by BRENDA team
Mycobacterium smegmatis MC2 155
-
-
-
Manually annotated by BRENDA team
Neurospora sp.
-
-
-
Manually annotated by BRENDA team
no activity in Aerobacter sp.
-
-
-
Manually annotated by BRENDA team
strain 170, trans-3-chloroacrylic acid dehydrogenase CaaD has phenylpyruvate tautomerase activity
-
-
Manually annotated by BRENDA team
Pseudomonas pavonaceae 170
strain 170
-
-
Manually annotated by BRENDA team
Pseudomonas pavonaceae 170
strain 170, trans-3-chloroacrylic acid dehydrogenase CaaD has phenylpyruvate tautomerase activity
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-
MIF is implicated in the pathogenesis of several inflammatory and autoimmune diseases
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
physiological function
-
MIF is involved in diverse biological processes, e.g. MIF glucocorticoid overriding activity, endotoxin lipopolysaccharide-induced TNF production, MIF-mediated stimulation of ERK1/2 MAP kinase and proliferation of serum-starved cells, MIF-mediated upregulation of arachidonic acid in macrophages, and Cox-2 activation
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
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(4-hydroxyphenyl)enolpyruvate
(4-hydroxyphenyl)pyruvate
show the reaction diagram
Mycobacterium smegmatis, Mycobacterium smegmatis MC2 155
-
-
-
-
?
(4-Hydroxyphenyl)pyruvate
?
show the reaction diagram
-
-
-
-
-
(Diiodohydroxyphenyl)pyruvate
?
show the reaction diagram
-
keto-form
-
-
-
2-oxo-3-pentynoate
acetopyruvate + ?
show the reaction diagram
Mycobacterium smegmatis, Mycobacterium smegmatis MC2 155
-
at pH 6.5, CCH2 exhibits hydratase activity and converts 2-oxo-3-pentynoate to acetopyruvate
-
-
?
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
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
-
-
-
3-(4-hydroxyphenyl)pyruvate
2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoate
show the reaction diagram
-
keto-form
enol-form
-
4-(hydroxyphenyl)pyruvate
4-(hydroxyphenyl)pyruvate
show the reaction diagram
-
enol form
keto form
-
?
cis-3-chloroacrylate
malonate semialdehyde + HCl
show the reaction diagram
Mycobacterium smegmatis, Mycobacterium smegmatis MC2 155
-
the reaction is performed by cis-CAAD
-
-
?
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
show the reaction diagram
-
-
-
r
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
show the reaction diagram
-
-
-
r
enol-(p-hydroxyphenyl)pyruvate
keto-(p-hydroxyphenyl)pyruvate
show the reaction diagram
-
-
-
-
?
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
-
-
?
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
-
r
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
-
r
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
reaction is stereoselective, generating the (3R) isomer of [3-D]phenylpyruvate in D2O in a ratio of 6.6:1
-
?
enol-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
-
reaction is stereoselective, generating the 3S isomer of [3-D]phenylpyruvate in a 18:1 ratio in D2O
-
-
?
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
P34884
-
-
r
keto-(p-hydroxyphenyl)pyruvate
enol-(p-hydroxyphenyl)pyruvate
show the reaction diagram
P14174
the substrate interacts with Pro1, Lys32 and Ile64 from one subunit and Tyr95 and Asn97 from an adjacent subunit
-
?
keto-phenylpyruvate
enol-phenylpyruvate
show the reaction diagram
P34884
-
-
r
keto-phenylpyruvate
enol-phenylpyruvate
show the reaction diagram
-
-
-
-
r
phenylenolpyruvate
phenylpyruvate
show the reaction diagram
-
-
-
-
?
phenylenolpyruvate
phenylpyruvate
show the reaction diagram
Pseudomonas pavonaceae, Pseudomonas pavonaceae 170
-
-
-
-
?
phenylenolpyruvate
phenylpyruvate
show the reaction diagram
Mycobacterium smegmatis MC2 155
-
-
-
-
?
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
-
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
-
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
-
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
r
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
r, 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
enol-form
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
keto-form
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
keto-form
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
keto-form
-
-
-
Phenylpyruvate
Phenylpyruvate
show the reaction diagram
-
keto-form
enol-form
-
Phenylpyruvate
?
show the reaction diagram
-
-
-
-
-
trans-3-chloroacrylate
malonate semialdehyde + HCl
show the reaction diagram
-
the reaction is performed by CAAD
-
-
?
keto-phenylpyruvate
keto-phenylpyruvate
show the reaction diagram
-
-
-
-
r
additional information
?
-
-
role in the biosynthesis of thyroxine
-
-
-
additional information
?
-
P14174
important immunoregulatory molecule with a unique ability to suppress the anti-inflammatory effects of glucocorticoids
-
?
additional information
?
-
-
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
-
?
additional information
?
-
-, Q9NAS2
the enzyme is chemotactic for human monocytes and activates them to produce IL-8, TNF-alpha and endogenous MIF
-
?
additional information
?
-
-
MIF is a homotrimeric multifunctional proinflammatory cytokine. It also shows dopachrome tautomerase activity. Binding of MIF to its receptor, CD74, overview
-
-
-
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, the N-terminal Pro is essential for the tautomerase activity of MIF
-
-
-
additional information
?
-
Mycobacterium smegmatis, Mycobacterium smegmatis MC2 155
-
CCH2 functions as an efficient PPT and exhibits low-level promiscuous dehalogenase activity, processing both cis- and trans-3-chloroacrylic acid
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
Phenylpyruvate
?
show the reaction diagram
-
-
-
-
-
keto-phenylpyruvate
enol-phenylpyruvate
show the reaction diagram
-
-
-
-
r
additional information
?
-
-
role in the biosynthesis of thyroxine
-
-
-
additional information
?
-
P14174
important immunoregulatory molecule with a unique ability to suppress the anti-inflammatory effects of glucocorticoids
-
?
additional information
?
-
-
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
-
?
additional information
?
-
-, Q9NAS2
the enzyme is chemotactic for human monocytes and activates them to produce IL-8, TNF-alpha and endogenous MIF
-
?
additional information
?
-
-
MIF is a homotrimeric multifunctional proinflammatory cytokine. It also shows dopachrome tautomerase activity. Binding of MIF to its receptor, CD74, overview
-
-
-
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
-
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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
-
i.e. ISO-I
(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-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
-
IC50 ketonase reaction 1.0 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.6 microM, pH 6.2, room temperatur
acetaminophen
-
-
acetoacetate
-
-
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
-
IC50 ketonase reaction 5.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 77.9 microM, pH 6.2, room temperatur
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
carnosic acid
-
IC50 ketonase reaction 15.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 115.8 microM, pH 6.2, room temperatur
carnosic acid
-
-
chlorogenic acid
-
IC50 ketonase reaction 7.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 127.0 microM, pH 6.2, room temperatur
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
-
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
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
-
IC50 ketonase reaction 31.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 85.3 microM, pH 6.2, 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
-
-
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
-
IC50 ketonase reaction 4.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 84.1 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
-
IC50 ketonase reaction 1.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 28.0 microM, pH 6.2, room temperatur
resveratrol
-
-
rosmarinic acid
-
IC50 ketonase reaction 13.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 65.6 microM, pH 6.2, room temperatur
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
-
IC50 ketonase reaction 2.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 19.5 microM, pH 6.2, room temperatur
umbelliferone
-
-
methyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
-
-
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
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.79
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
0.89
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
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
-
-
0.1
-
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
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme Y95F
0.11
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme Y97A
0.14
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme K32A
0.143
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme P1G
0.17
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5
0.2
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, wild-type enzyme
0.35
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme K32R
0.582
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, 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
-
23C, pH 6.5, mutant enzyme K32R
0.107
-
enol-phenylpyruvate
-
23C, mutant enzyme P1G
0.112
-
enol-phenylpyruvate
-
23C, mutant enzyme Y95F
0.113
-
enol-phenylpyruvate
-
mutant E52Q, pH 9.0
0.13
-
enol-phenylpyruvate
-
23C, pH 6.5
0.15
-
enol-phenylpyruvate
-
23C, pH 6.5, wild-type enzyme
0.16
-
enol-phenylpyruvate
-
mutant E16A, pH 6.8
0.18
-
enol-phenylpyruvate
-
23C, pH 6.5, mutant enzyme K32A
0.18
-
enol-phenylpyruvate
-
23C, mutant enzyme N97A
0.303
-
enol-phenylpyruvate
-
23C, mutant enzyme P1A
0.31
-
enol-phenylpyruvate
-
23C, wild-type enzyme
2.77
-
keto-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5
4.9
-
Keto-phenylpyruvate
-
23C, pH 6.5
0.11
-
phenylenolpyruvate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
0.25
-
phenylenolpyruvate
-
mutant enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
3.5
-
phenylenolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
6
-
phenylpyruvate
-
-
6.1
-
phenylpyruvate
-
keto-form, kidney
8
-
phenylpyruvate
-
thyroid gland
96
-
trans-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.2
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
3.2
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
0.052
-
(4-hydroxyphenyl)pyruvate
-
enol-form, kidney
1.89
-
(4-hydroxyphenyl)pyruvate
-
keto-form, kidney
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 22C
-
0.8
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, mutant enzyme P1G
4.1
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme P1A
15
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme K32A
58
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme N97A
126
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme Y95F
140
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, wild-type enzyme
160
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, mutant enzyme K32R
160
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5
160
-
enol-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5, wild-type enzyme
0.6
-
enol-phenylpyruvate
-
23C, mutant enzyme P1G
1.4
-
enol-phenylpyruvate
-
wild-type, pH 9.0
1.7
-
enol-phenylpyruvate
-
23C, mutant enzyme P1A
4.1
-
enol-phenylpyruvate
-
mutant E52Q, pH 9.0
30
-
enol-phenylpyruvate
-
23C, pH 6.5, mutant enzyme K32A
33
-
enol-phenylpyruvate
-
pH 9.0
38
-
enol-phenylpyruvate
-
pH 6.8
109
-
enol-phenylpyruvate
-
23C, mutant enzyme Y95F
150
-
enol-phenylpyruvate
-
23C, pH 6.5, mutant enzyme K32R
200
-
enol-phenylpyruvate
-
mutant E16A, pH 6.8
290
-
enol-phenylpyruvate
-
23C, pH 6.5
320
-
enol-phenylpyruvate
-
23C, pH 6.5, wild-type enzyme
410
-
enol-phenylpyruvate
-
23C, wild-type enzyme
660
-
enol-phenylpyruvate
-
23C, mutant enzyme N97A
0.03
-
keto-(p-hydroxyphenyl)pyruvate
P14174
25C, pH 6.0, mutant enzyme P1(A)M2
0.93
-
keto-(p-hydroxyphenyl)pyruvate
P14174
25C, pH 6.0, mutant enzyme P1G
2.7
-
keto-(p-hydroxyphenyl)pyruvate
P14174
25C, pH 6.0, wild-type enzyme
6.08
-
keto-(p-hydroxyphenyl)pyruvate
P14174
25C, pH 6.0, mutant enzyme P1G
120
-
keto-(p-hydroxyphenyl)pyruvate
-
23C, pH 6.5
285
-
Keto-phenylpyruvate
-
23C, pH 6.5
0.2
-
phenylenolpyruvate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
0.8
-
phenylenolpyruvate
-
mutant enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
34
-
phenylenolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
-
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 22C
-
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2.5
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
3.5
-
(4-hydroxyphenyl)enolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
1.6
-
cis-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
0
30
-
cis-3-chloroacrylate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
1.8
-
phenylenolpyruvate
-
wild type enzyme cis-CAAD, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
3.3
-
phenylenolpyruvate
-
mutant enzyme CCH2-P1A, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
9.8
-
phenylenolpyruvate
-
wild type enzyme CCH2, in 10 mM Na2HPO4 buffer, pH 7.3, at 22C
0
4
-
trans-3-chloroacrylate
-
wild type enzyme CCH2, in in 50 mM Tris-SO4 buffer (pH 8.0), at 22C
0
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0026
-
(E)-2-fluoro-o-hydroxycinnamate
-
23C, pH 6.5
0.013
-
(E)-2-fluoro-p-hydroxycinnamate
-
23C, pH 6.5, mutant enzyme N97A
0.03
-
(E)-2-fluoro-p-hydroxycinnamate
-
23C, pH 6.5, mutant enzyme K32R
0.04
-
(E)-2-fluoro-p-hydroxycinnamate
-
23C, pH 6.5, mutant enzyme K32A
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
-
4-coumaric acid
-
23C, pH 6.5, mutant enzyme K32R
0.375
-
4-coumaric acid
-
23C, pH 6.5, mutant enzyme K32A
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]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0025
-
(2Z)-2-(2-methoxybenzylidene)cyclopentanone
-
-
0.00079
-
(2Z)-2-(4-bromobenzylidene)cyclopentanone
-
-
0.0031
-
(2Z)-2-(4-methoxybenzylidene)cyclohexanone
-
-
0.0039
-
(2Z)-2-(4-methoxybenzylidene)cyclopentanone
-
-
0.0056
-
(2Z)-2-(pyridin-2-ylmethylene)-3,4-dihydronaphthalen-1(2H)-one
-
-
0.0062
-
(2Z)-2-benzylidenecyclopentanone
-
22C, pH 6.5
0.0016
-
(2Z,5Z)-2,5-dibenzylidenecyclopentanone
-
-
0.0062
-
(3Z)-3-[4-(dimethylamino)benzylidene]-7-hydroxy-2H-chromene-2,4(3H)-dione
-
-
0.0026
-
(E)-2-fluoro-4-hydroxycinnamate
-
-
0.073
-
(E)-2-fluoro-cinnamate
-
-
0.073
-
(E)-2-fluorocinnamate
-
-
0.0015
-
(E)-4-hydroxycinnamate
-
-
0.007
-
(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
0.013
-
(S)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester
-
-
0.48
-
(Z)-2-fluoro-4-hydroxycinnamate
-
-
2.33
-
(Z)-2-fluoro-cinnamate
-
-
2.33
-
(Z)-2-fluorocinnamate
-
-
0.21
-
(Z)-4-hydroxycinnamate
-
-
0.00161
-
2,5-dibenzylidenecyclopentanone
-
-
0.0016
-
2-oxo-2-phenylethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
-
0.0031
-
2-piperidinoethyl isothiocyanate
-
-
0.000038
-
3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
-
-
0.0043
-
3-acetyl-7-hydroxy-2H-chromen-2-one
-
-
0.5
-
3-hydroxy-acetaminophen
-
-
0.0015
-
3-[4-(1,3-benzodioxol-5-yl)-1,3-thiazol-2-yl]-7-hydroxy-2H-chromen-2-one
-
-
0.0029
-
7-hydroxy-2-oxo-2H-chromene-3-carbonitrile
-
-
0.00055
-
7-hydroxy-2-oxo-2H-chromene-3-carbothioamide
-
-
0.0021
-
7-hydroxy-3-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one
-
-
0.0031
-
7-hydroxy-3-(4-methyl-1,3-thiazol-2-yl)-2H-chromen-2-one
-
-
0.0005
-
7-hydroxy-3-(pyrazolo[1,5-a]pyridin-2-yl)-2H-chromen-2-one
-
-
0.00047
-
7-hydroxy-3-phenyl-2H-chromen-2-one
-
-
0.00028
-
7-hydroxy-3-[4-(2-oxo-2H-chromen-3-yl)-1,3-thiazol-2-yl]-2H-chromen-2-one
-
-
0.001
-
acetaminophen
-
IC50 ketonase reaction 1.0 microM, pH 6.5, room temperatur
0.0026
-
acetaminophen
-
IC50 enolase reaction 2.6 microM, pH 6.2, room temperatur
10
-
acetaminophen
-
-
0.0037
-
allyl isothiocyamate
-
-
0.0013
-
AVP-13546
-
-
-
0.0008
-
Benzyl isothiocyanate
-
-
0.0057
-
boldine
-
IC50 ketonase reaction 5.7 microM, pH 6.5, room temperatur
0.0779
-
boldine
-
IC50 enolase reaction 77.9 microM, pH 6.2, room temperatur
0.0005
0.002
caffeic acid
-
IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
0.0155
-
carnosic acid
-
IC50 ketonase reaction 15.5 microM, pH 6.5, room temperatur
0.1158
-
carnosic acid
-
IC50 enolase reaction 115.8 microM, pH 6.2, room temperatur
0.0076
-
chlorogenic acid
-
IC50 ketonase reaction 7.6 microM, pH 6.5, room temperatur
0.127
-
chlorogenic acid
-
IC50 enolase reaction 127.0 microM, pH 6.2, room temperatur
0.0209
0.2296
Cinnamic acid
-
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
-
IC50 ketonase reaction 88.8 microM, pH 6.5, room temperatur
0.0007
-
curcumin
-
IC50 ketonase reaction 0.7 microM, pH 6.5, room temperatur
0.0122
-
curcumin
-
IC50 enolase reaction 12.2 microM, pH 6.2, room temperatur
0.0058
-
ethyl 3-(7-hydroxy-2-oxo-2H-chromen-3-yl)-3-oxopropanoate
-
-
0.0074
-
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
-
-
0.0111
-
ethyl isothiocyanate
-
-
0.1659
-
Eugenol
-
IC50 ketonase reaction 165.9 microM, pH 6.5, room temperatur
0.0317
-
ferulic acid
-
IC50 ketonase reaction 31.7 microM, pH 6.5, room temperatur
0.0853
-
ferulic acid
-
IC50 enolase reaction 85.3 microM, pH 6.2, room temperatur
0.0627
-
folic acid
-
IC50 ketonase reaction 62.7 microM, pH 6.5, room temperatur
0.0802
-
folic acid
-
80.2 microM; IC50 enolase reaction 80.2 microM, pH 6.2, room temperatur
0.0369
-
galangin
-
IC50 ketonase reaction 36.9 microM, pH 6.5, room temperatur
0.1437
-
galangin
-
IC50 enolase reaction 143.7 microM, pH 6.2, room temperatur
0.1096
-
Ibuprofen
-
IC50 enolase reaction 109.6 microM, pH 6.2, room temperatur
10.3343
-
Ibuprofen
-
IC50 ketonase reaction 10334.3 microM, pH 6.5, room temperatur
0.0504
-
Isoeugenol
-
IC50 ketonase reaction 50.4 microM, pH 6.5, room temperatur
0.129
-
Isoeugenol
-
IC50 enolase reaction 129.0 microM, pH 6.2, room temperatur
0.0014
-
methallyl isothiocyanate
-
-
0.0156
-
methotrexate
-
IC50 ketonase reaction 15.6 microM, pH 6.5, room temperatur
0.0637
-
methotrexate
-
IC50 enolase reaction 63.7 microM, pH 6.2, room temperatur
0.0007
-
N-acetyl-3-hydroxy-4-benzoquinone imine
-
-
0.04
-
N-acetyl-4-benzoquinone imine
-
-
0.0878
-
o-coumaric acid
-
IC50 ketonase reaction 87.8 microM, pH 6.5, room temperatur
0.1757
-
o-coumaric acid
-
IC50 enolase reaction 175.7 microM, pH 6.2, room temperatur
0.0181
0.1033
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
3.6241
-
parthenolide
-
IC50 ketonase reaction 3624.1 microM, pH 6.5, room temperatur
0.3766
-
Phenylbutazone
-
IC50 enolase reaction 376.6 microM, pH 6.2, room temperatur
7.1267
-
Phenylbutazone
-
IC50 ketonase reaction 7126.7 microM, pH 6.5, room temperatur
0.0048
-
phloretin
-
IC50 ketonase reaction 4.8 microM, pH 6.5, room temperatur
0.0841
-
phloretin
-
IC50 enolase reaction 84.1 microM, pH 6.2, room temperatur
0.0748
-
piroxicam
-
IC50 enolase reaction 74.8 microM, pH 6.2, room temperatur
0.1209
-
piroxicam
-
IC50 ketonase reaction 120.9 microM, pH 6.5, room temperatur
0.0349
-
Quinine
-
IC50 ketonase reaction 34.9 microM, pH 6.5, room temperatur
0.1563
-
Quinine
-
IC50 enolase reaction 156.3 microM, pH 6.2, room temperatur
0.0019
-
resveratrol
-
IC50 ketonase reaction 1.9 microM, pH 6.5, room temperatur
0.028
-
resveratrol
-
IC50 enolase reaction 28.0 microM, pH 6.2, room temperatur
0.0138
-
rosmarinic acid
-
IC50 ketonase reaction 13.8 microM, pH 6.5, room temperatur
0.0656
-
rosmarinic acid
-
IC50 enolase reaction 65.6 microM, pH 6.2, room temperatur
0.1338
-
scopoletin
-
IC50 ketonase reaction 133.8 microM, pH 6.5, room temperatur
0.0026
0.0195
umbelliferone
-
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]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2.3
-
-
-
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.2
8.2
-
no real optimum
6.2
-
-
-
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
39000
44000
-
gel filtration, sucrose density gradient centrifugation
48000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 12000, SDS-PAGE
?
-
x * 12316, mutant enzyme K32A, electrospray ionization mass spectrometry; x * 12371, wild-type enzyme, electrospray ionization mass spectrometry; x * 12401, mutant enzyme K32R, electrospray ionization mass spectrometry
?
P14174
x * 12345, wild-type enzyme, mass spectrometry
?
-
x * 12335, electrospray ionization mass spectrometry, mutant enzyme P1G; x * 12347, electrospray ionization mass spectrometry, mutant enzyme N97A; x * 12347, electrospray ionization mass spectrometry, mutant enzyme P1A; x * 12358, electrospray ionization mass spectrometry, mutant enzyme Y95F; x * 12371, electrospray ionization mass spectrometry, wild-type enzyme
?
-, Q9NAS2
x * 13100, Bm-MIF-2, calculation from nucleotide sequence
?
-
x * 12000, SDS-PAGE
heterohexamer
-
-
heterohexamer
Pseudomonas pavonaceae 170
-
-
-
homotrimer
-
3 * 16093, electrospray ionization mass spectrometry; 3 * 16223, calculated from amino acid sequence
homotrimer
Mycobacterium smegmatis MC2 155
-
3 * 16093, electrospray ionization mass spectrometry; 3 * 16223, calculated from amino acid sequence
-
trimer
-
trimer formation is required for MIF tautomerase activity, trimer three-dimensional structure and tautomerase active site structure. The subunit interface is not as hydrophobic as the interior of the monomer, however, there is a hydrophobic patch on the surface involving residues Y36, Y95, W108, and F113, MALDI-TOF and analytical gel filtration analysis, overview
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
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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
-, Q9NAS2
hanging drop vapor diffusion method, crystal structure of the enzyme complexed with p-hydroxyphenylpyruvate
P14174
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
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
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 ACCESSION NO.
LITERATURE
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
-
-10C, stable for several months
-
-20C, 6 weeks, no loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
simple method for purification based on size-exclusion chromatography on Toyopearl TSK polymer having a tendencey to adsorb the enzyme
-
recombinant MIF from Escherichia coli strain BL21(DE3) by anion exchange chromatography and gel filtration
-
recombinant enzyme
-
Ni-Sepharose column chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-
-, Q9NAS2
expression in Escherichia coli strain BL21(DE3)
-
expression in Escherichia coli, via pKK223-3 expression vector
-
expression in Escherichia coli
-
wild-type and mutant enzymes P1G, P1A, Y95F and N97A, expression in Escherichia coli BL21
-
expressed in Escherichia coli BL21(DE3) cells
-
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
MIF expression is upregulated by cytokines, TNF-alpha and interleukin-I, and by bacterial endotoxins, such as lipopolysaccharides, and exotoxins
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
P1(A)M2
P14174
insertion abolishes activity
P1G
P14174
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
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
Mycobacterium smegmatis MC2 155
-
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)
-
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
Pseudomonas pavonaceae 170
-
mutation in alpha-subunit, 1.6fold increase in ratio of kcat to Km value
-
P1A
Pseudomonas pavonaceae 170
-
mutation in beta-subunit, 8fold decrease in ratio of kcat to Km value
-
R11A
Pseudomonas pavonaceae 170
-
mutation in alpha-subunit, 15fold decrease in ratio of kcat to Km value
-
R8A
Pseudomonas pavonaceae 170
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
drug development
-
the tautomerase activity of MIF is a target for inhibitor development, overview