5.3.2.1: phenylpyruvate tautomerase
This is an abbreviated version!
For detailed information about phenylpyruvate tautomerase, go to the full flat file.
Word Map on EC 5.3.2.1
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5.3.2.1
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necrosis
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monocyte
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tnf
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endothelial
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lymphocyte
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chemokine
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autoimmune
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anti-mif
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glucocorticoid
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arthritis
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pulmonary
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artery
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leukocyte
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angiogenesis
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sepsis
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rheumatoid
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tnf-alpha
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lipopolysaccharide
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factor-alpha
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myocardial
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t-cells
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atherosclerosis
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chemotactic
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c-reactive
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pituitary
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chemoattractant
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infarct
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lupus
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lymphokine
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toll-like
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autocrine
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cxcr2
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synovial
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ifn-gamma
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il-1beta
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counter-regulator
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chemokine-like
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erythematosus
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immunoregulatory
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cell-mediated
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glomerulonephritis
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dehalogenation
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tautomerization
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counterregulates
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delayed-type
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pro-tumorigenic
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drug development
- 5.3.2.1
- necrosis
- monocyte
- tnf
- endothelial
- lymphocyte
- chemokine
- autoimmune
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anti-mif
- glucocorticoid
- arthritis
- pulmonary
- artery
- leukocyte
- angiogenesis
- sepsis
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rheumatoid
- tnf-alpha
- lipopolysaccharide
- factor-alpha
- myocardial
- t-cells
- atherosclerosis
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chemotactic
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c-reactive
- pituitary
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chemoattractant
- infarct
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lupus
- lymphokine
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toll-like
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autocrine
- cxcr2
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synovial
- ifn-gamma
- il-1beta
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counter-regulator
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chemokine-like
- erythematosus
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immunoregulatory
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cell-mediated
- glomerulonephritis
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dehalogenation
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tautomerization
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counterregulates
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delayed-type
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pro-tumorigenic
- drug development
Reaction
Synonyms
CaaD, CCH2, cis-3-chloroacrylic acid dehalogenase, cis-CaaD, Macrophage migration inhibitory factor, macrophage migration inhibitory factor tautomerase, MIF, MIF tautomerase, phenyl(enol)pyruvate tautomerase, Phenylpyruvate keto-enol tautomerase, Phenylpyruvic keto-enol isomerase, PPT, Tautomerase, phenylpyruvate, trans-3-chloroacrylic acid dehalogenase
ECTree
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Inhibitors
Inhibitors on EC 5.3.2.1 - phenylpyruvate tautomerase
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(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
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2,2-dimethylpropyl [3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
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2,4,6-trimethylphenyl [3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
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2-Oxo-3-pentynoate
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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-[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
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2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-N-(4-methoxyphenyl)acetamide
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AV1013
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noncompetitive inhibitor of the p-hydroxyphenylpyruvate tautomerase activity of MIF
AV411
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ibudilast, i.e. 3-isobutyryl-2-isopropylpyrazolo-[1,5-a]pyridine, noncompetitive inhibitor of the p-hydroxyphenylpyruvate tautomerase activity of MIF
AVP-13546
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inhibits the tautomerase activity of MIF and reduces cytokine, including TNF-alpha, levels in vivo
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Benzyl isothiocyanate
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specific inhibition of MIF tautomerase activity is mediated by selective modification of the N-terminal proline
caffeic acid
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IC50 ketonase reaction 0.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.0 microM, pH 6.2, room temperatur
Cinnamic acid
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IC50 ketonase reaction 20.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 229.6 microM, pH 6.2, room temperatur
ethyl 7-hydroxy-2-oxo-2H-chromene-3-carboxylate
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inhibition mechanism, overview
folic acid
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IC50 ketonase reaction 62.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 80.2 microM, pH 6.2, room temperatur
galangin
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IC50 ketonase reaction 36.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 143.7 microM, pH 6.2, room temperatur
Ibuprofen
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IC50 ketonase reaction 10334.3, pH 6.5, room temperatur, IC50 enolase reaction 109.6 microM, pH 6.2, room temperatur
isoeugenol
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IC50 ketonase reaction 50.4 microM, pH 6.5, room temperatur, IC50 enolase reaction 129.0 microM, pH 6.2, room temperatur
methotrexate
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IC50 ketonase reaction 15.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 63.7 microM, pH 6.2, room temperatur
N-(4-aminobutyl)-2-[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetamide
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o-coumaric acid
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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
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IC50 ketonase reaction 18.1 microM, pH 6.5, room temperatur, IC50 enolase reaction 103.3 microM, pH 6.2, room temperatur
Phenylbutazone
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IC50 ketonase reaction 7126.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 376.6 microM, pH 6.2, room temperatur
piroxicam
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IC50 ketonase reaction 120.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 74.8 microM, pH 6.2, room temperatur
Quinine
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IC50 ketonase reaction 34.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 156.3 microM, pH 6.2, room temperatur
tert-butyl [4-({[3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl}amino)butyl]carbamate
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i.e. ISO-I
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IC50 ketonase reaction 1.0 microM, pH 6.5, room temperatur, IC50 enolase reaction 2.6 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 5.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 77.9 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 15.5 microM, pH 6.5, room temperatur, IC50 enolase reaction 115.8 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 7.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 127.0 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 0.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 12.2 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 31.7 microM, pH 6.5, room temperatur, IC50 enolase reaction 85.3 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 4.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 84.1 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 1.9 microM, pH 6.5, room temperatur, IC50 enolase reaction 28.0 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 13.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 65.6 microM, pH 6.2, room temperatur
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IC50 ketonase reaction 2.6 microM, pH 6.5, room temperatur, IC50 enolase reaction 19.5 microM, pH 6.2, room temperatur
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50% inhibition could not be attained: estragol, gentisic acid, tropolone
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additional information
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design and synthesis of irreversible isothiocyanate-based inhibitors of MIF, inhibitory potencies and inhibition mechanism, overview
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additional information
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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
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