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Enzyme Nomenclature
Information on EC 1.13.11.27 - 4-hydroxyphenylpyruvate dioxygenase
for references in articles please use BRENDA:EC1.13.11.27
Word Map on EC 1.13.11.27
- 1.13.11.27
- viral
-
syncytial
- glycoprotein
- viruses
- newcastle
- paramyxovirus
- measles
- parainfluenza
-
sendai
- hemagglutinin-neuraminidase
- infant
-
heptad
- homogentisate
-
fusogenic
-
herbicide
-
virion
-
hemagglutinin
-
immunogen
- metapneumovirus
-
anti-f
- tyrosinemia
- mumps
- distemper
- paramyxoviridae
-
prefusion
-
outbreak
- furin
-
ectodomains
-
six-helix
-
rsv-infected
-
velogenic
-
nucleocapsids
-
postfusion
-
nipah
-
virus-specific
-
cleavability
- nucleopolyhedrovirus
-
virus-like
- morbillivirus
-
virus-cell
- panencephalitis
- agriculture
- environmental protection
- diagnostics
- acmnpv
- fumarylacetoacetate
- rinderpest
-
formalin-inactivated
- plastoquinone
- drug development
-
rsv-induced
-
edmonston
- medicine
-
merger
-
virus-neutralizing
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The expected taxonomic range for this enzyme is: Eukaryota, Archaea, Bacteria
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EC NUMBER 
COMMENTARY 
1.13.11.27
-
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RECOMMENDED NAME
GeneOntology No.
4-hydroxyphenylpyruvate dioxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
homogentisate
-
-
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
rate-determining step in catalysis is a protein conformation change
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mono-iso-ordered bi-bi mechanism with binding of 4-hydroxyphenylpyruvate before O2 and release of CO2 before homogentisate. A Theorell-Chance mechanism can not be excluded
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
enzyme form 3: ordered bi bi mechanism where 4-hydroxyphenylpyruvate is added prior to oxygen and CO2 released before homogentisate
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
evidence against participation of a quinol as a free intermediate
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
in plants this enzyme activity is involved in two distinct metabolic processes, the biosynthesis of prenylquinones and the catabolism of tyrosine
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
addition of substrate and oxygen to the holoenzyme is formally random, holo-enzym in complex with substrate has a 3600-fold increase in oxygen reactivity
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
ternary enzyme-substrate complex is firstly decarboxylated to the iron(II)-peracid intermediate followed by heterolytic cleavage of the O-O bond yielding an iron(IV)-oxospecies. This attacks the aromatic ring in C1 position. The arene oxide has no catalytic relevance
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mechanism of oxygen binding and activation, structural relationship to other dioxygenases
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
the C-terminal helix forms a gate for substrate access to the active site around a nonheme ferrous iron center
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
the C-terminal helix forms a gate for substrate access to the active site around a nonheme ferrous iron center, completely sequestering the active site from solvent
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
The data of the rapid acid quench followd by HPLC product analysis, indicate that the homogenisate product is formed during one turnover, as the amount of product is equivalent to the enzyme-substrate complex at 191 ms.
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
direct involvement of the arene oxide intermediate to the reaction mechanism
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, inhibitor-bound crystal structure, PDB ID 1CJX, analysis, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum mechanics/molecular mechanics calculations and simulations, detailed overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
reaction mechanism, quantum mechanics/molecular mechanics calculations and simulations, detailed overview
-
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
mono-iso-ordered bi-bi mechanism with binding of 4-hydroxyphenylpyruvate before O2 and release of CO2 before homogentisate. A Theorell-Chance mechanism can not be excluded
-
-
4-hydroxyphenylpyruvate + O2 = homogentisate + CO2
dioxygen reactivity and the common decarboxylation half reaction, and the hydroxylation half reaction, mechanisms, detailed overview
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
-
-
-
-
hydroxylation
-
-
-
-
redox reaction
-
-
-
-
side-chain migration
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxyphenylpyruvate:oxygen oxidoreductase (hydroxylating, decarboxylating)
The Pseudomonas enzyme contains one Fe3+ per mole of enzyme; the enzymes from other sources may contain essential iron or copper.
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CAS REGISTRY NUMBER
COMMENTARY
9029-72-5
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
Swissprot
sequence of the cloned 4-hydroxyphenylpyruvate dioxygenase coincides with published 4-hydroxyphenylpyruvate dioxygenase-sequences from Arabidopsis thaliana to a nearly perfect identity match except for minor differences in the C-terminal parts of the cDNA.
Swissprot
The alpha-tocophenol content is increased in leaves of the transgenic Nicotiana tabacum (tabacco) plants, whereas the transgenic tobacco seeds contain a significantly increased gamma-tocochromanol level. Overexpression of the barley 4-hydroxyphenylpyruvate dioxygenase gene in plastids of tobacco does not prove to be advantageous in comparison to transgenic tobacco plants expressing high 4-hydroxyphenylpyruvate dioxygenase level in the cytoplasma.
Swissprot
4-hydroxyphenylpyruvate dioxygenase of Pseudomonas fluroscens is cloned into Nicotiana tabacum (cv. PBD6) and into Glycine max (cv. Jack) and tobacco plastid transformants acquire a strong herbicide tolerance, performing better than nuclear transformants.
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-
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
evolution
-
4-hydroxyphenylpyruvate dioxygenase and hydroxymandelate synthase, HMS, EC 1.13.11.46, catalyze similar reactions using the same substrates, 4-hydroxyphenylpyruvate and dioxygen. Initially, both enzymes reduce and activate dioxygen in order to decarboxylate 4-hydroxyphenylpyruvate, yielding 4-hydroxyphenylacetate, CO2, and an activated oxo intermediate Both enzymes then hydroxylate 4-hydroxyphenylacetate but do so in different positions
evolution
-
the enzyme belongs to the non-haem Fe(II)/2-oxoacid-dependent oxygenase superfamily, which couples the oxidative decarboxylation of a 2-oxoacid (most commonly a-ketoglutarate) to the oxidation of the prime substrate
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
evolution
-
4-hydroxyphenylpyruvate dioxygenase (HPPD) and hydroxymandelate synthase (HMS, EC 1.13.11.46) are outliers within the 2-oxo acid dependent oxygenase (aKAO) family. HPPD and HMS catalyze the chemistry of the majority of enzymes within the aKAO family but are clearly mechanistically convergent, having a grossly different structural topology. Some of the unique characteristics of HPPD and HMS have elucidated select parts of the catalytic cycle that are obscured in other family members. Moreover, the inhibitory chemistry of HPPD is a phenomenon with ever-expanding relevance across all kingdoms of life
-
malfunction
-
deficiency in active 4-HPPD in humans results in type III tyrosinemia, a rare autosomal recessive disorder
malfunction
-
neutrophil preparations from a patient with tyrosinemia type III, with inherited deficiency of 4-hydroxyphenylpyruvate dioxygenase (HPPD), exhibit a far higher NO release than controls, when NO is estimated in terms of nitrite content in the suspending media. L-tyrosine increases nitrite release and accumulation in suspending media of U-937 cells, a human monoblast-like lymphoma cell line which displays many characteristics of macrophages, including the expression of inducible and endothelial nitric oxide synthases. The increase of nitrite release by patient's neutrophils might be related to the presence of high L-tyrosine concentrations in the blood samples rather than to HPPD deficiency of in these cells
malfunction
-
inhibition of HPPD can effectively alleviate the symptoms of type I tyrosinemia
malfunction
-
when HPPD is inhibited, the plant is severely damaged by sunlight, becoming bleached and eventually undergoing necrosis and death. HPPD inhibitors are termed bleaching herbicides
malfunction
mutant plants with null alleles of HPPD are reported to exhibit a lethal photobleaching phenotype. MsHPPD expression in three MsHPPD-overexpressing transgenic lines and wild-type, overview
metabolism
-
inhibition mechanism of 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
metabolism
-
enzyme 4-HPPD catalyzes the second step in the pathway of tyrosine catabolism, the conversion of 4-hydroxyphenyl-pyruvate to homogentisate
metabolism
-
hydroxyphenylpyruvate dioxygenase catalyzes the second step in the pathway of L-tyrosine catabolism, the conversion of 4-hydroxyphenylpyruvate to homogentisate
metabolism
-
4-ydroxyphenylpyruvate dioxygenase (HPPD) is an essential enzyme in tyrosine catabolism
metabolism
-
the enzyme is ivolved in the tyrosine catabolic pathway, it catalyzes the synthesis of the central compound homogentisate and plays an important role, overview
metabolism
-
suggested hydroxylation mechanisms for HMS and HPPD and pathways leading to alternative products: oxepinone and quinolacetate
metabolism
-
the enzyme is involved in the second step of the tyrosine degradation pathway, catalyzing the conversion of 4-hydroxyphenylpyruvate to homogentisate
metabolism
enzyme HPPD is the first committed enzyme involved in the biosynthesis of vitamin E. Vitamin E is not a single compound, but rather the collective name for a group of eight lipid-soluble antioxidants consisting of a polar chromanol head group and a hydrophobic prenyl tail, which are derived from the methylerythritol-4-phosphate (MEP) and shikimate pathways. Four of these compounds are termed tocopherols, and the other four are termed tocotrienols, and depending on the saturation level of the hydrophobic tail and also the number and position of the methyl groups on the chromanol ring, members of the vitamin E group are classified into alpha-, beta-, gamma- and delta-forms. In plants, the production of HGA is the first step in tocopherol synthesis, and homogentisic acid (HGA) is synthesized from p-hydroxyphenyl pyruvate (HPP) in a reaction catalyzed by enzyme HPPD
metabolism
-
suggested hydroxylation mechanisms for HMS and HPPD and pathways leading to alternative products: oxepinone and quinolacetate
-
physiological function
-
involved in aromatic amino acid metabolism
physiological function
Vitis vinifera x Vitis vinifera
-
involved in aromatic amino acid metabolism
physiological function
-
the enzyme catalyzes the synthesis of homogentisate, a precursor of plastoquinone, a diene-dione molecule, that serves as a lipid soluble electron carrier linking photosystems and shuttling electrons through the electron transport chain. Homogentiate is also the precursor to tocopherols (vitamin E) that serve as antioxidants and plant hormones. As such photosynthetic life is inseparably dependent on tyrosine catabolism and nature has developed a number of allelopathic molecules that target HPPD and thus homogenetisate production
physiological function
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enzyme HPPD is upregulated during the hyphal to yeast morphological transition that occurs when Paracoccidiodes brasiliensis fungus becomes pathogeneic
physiological function
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enzyme HPPD activity is one of the key factors influencing the production of tocopherols, overview
physiological function
4-hydroxyphenylpyruvate dioxygenase is involved in vitamin E biosynthesis and abscisic acid-mediated seed germination in Medicago sativa. MsHPPD functions not only in the vitamin E biosynthetic pathway, but also plays a critical role in seed germination via affecting abscisic acid biosynthesis and signaling, overview. HPPD is essential for plant viability
additional information
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substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Three different models of HPP binding within the Arabidopsis thaliana HPPD active site. Residues Ser246, Asn261, Gln272, Gln286, and Gln358 are important for catalysis
additional information
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substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser260, Asn275, Gln286, Gln300, and Gln372 are important for catalysis
additional information
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substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser201, Asn216, Gln225, Gln239, and Gln309 are important for catalysis
additional information
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substrate binding, structure modeling, structure comparisons, quantum mechanical/molecular mechanical calculations of the enzyme-substrate complex and key reaction intermediates, overview. Residues Ser201, Asn216, Gln226, Gln230, and Gln305 are important for catalysis
additional information
-
the disordered C-terminal tail of the enzyme, which is extended C-terminus compared to other 4-HPPD enzymes, plays an important role in catalysis with a critical role of residue Q375 in orientating the tail and ensuring the conformation of the terminal alpha-helix to maintain the integrity of the active site for catalysis. The active site of 4-HPPD is enclosed by a C-terminal alpha-helix which is assumed to function as a gate which controls access of substrate. Interactions provided by Q375 to hold the terminal helix and the tail in proper position are critical for isolating the active site from solvent during catalysis, enzyme structure modeling, overview
additional information
-
molecular dynamics simulations are performed for the HPPD-Fe(IV)=O-hydroxyphenylacetate complex in order to obtain a reliable starting structure for quantum mechanics/molecular mechanics calculations of ring hydroxylation and coupled rearrangement reactions catalyzed by the enzyme HPPD, structure of HPPD-Fe(II)-acetate complex, structure homology modeling, overview
additional information
-
enzyme molecular docking study using crystal structure PDB ID 1TG5. Three amino acid residues compose the active site: Gln358, His205 and Phe398
additional information
-
enzyme molecular docking study using crystal structure PDB ID 1SQI
additional information
-
molecular dynamics simulations are performed for the HPPD-Fe(IV)=O-hydroxyphenylacetate complex in order to obtain a reliable starting structure for quantum mechanics/molecular mechanics calculations of ring hydroxylation and coupled rearrangement reactions catalyzed by the enzyme HPPD, structure of HPPD-Fe(II)-acetate complex, structure homology modeling, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-hydroxyphenylpyruvate + O2
2,5-dihydroxyphenylacetate + CO2
-
-
-
?
(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
-
-
-
?
(2-fluoro-4-hydroxyphenyl)pyruvate + O2
(3-fluoro-2,5-dihydroxyphenyl)pyruvate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
4-hydroxyphenylpyruvate dioxygenase does not use phenolpyruvate as a substrate in normal plant metabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
evidence against participation of a quinol as a free intermediate
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme is involved in production of homogentisate, the aromatic precursor of all phenylquinones
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
activity with the keto-form of 4-hydroxyphenylpyruvate is 40times higher than with the enol tautomer
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
key enzyme involved in tyrosine catabolism, congenital 4-hydroxyphenylpyruvate dioxygenase deficiency is a rare, relatively benign condition known as hereditary type III tyrosinemia
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
the conversion of 4-hydroxyphenyl-pyruvate to homogentisate involves oxidative decarboxylation, side-chain migration and aromatic hydroxylation in a single catalytic cycle. The 4-HPPD reaction is unusual in that the 2-oxoacid and prime substrate moieties are contained within the same molecule
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Shewanella oneidensis MR-1 / ATCC 700550
-
homogentisate is an intermediate of the tyrosine degradation pathway, and a precursor of a redox-cycling metabolite, pyomelanin
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
hppD is transcriptionally activated by HpdA and repressed by HpdR
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme participates in catabolism of tyrosine
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 85% homogentisate and 15% 4-hydroxyphenylacetate
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 90% homogentisate, 1% quinolacetate, and 9% 4-hydroxyphenylacetate
-
?
phenylpyruvate + O2
2-hydroxyphenylacetate + CO2
-
at 10% of the activity with 4-hydroxyphenylpyruvate
-
-
?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
-
substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed
-
-
?
[(4-hydroxyphenyl)thio]pyruvate + O2
[(4-hydroxyphenyl)sulfinyl]acetate + CO2
-
substrate undergoes oxidative decarboxylation and sulfoxidation to give [(4-hydroxyphenyl)sulfinyl]acetate, ring oxidation is not observed
-
-
?
additional information
?
-
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
-
additional information
?
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
-
additional information
?
-
no activity is observed for 3-hydroxyphenylpyruvate, 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylglyoxylate, phenylpyruvate, 2-oxoglutarate, glyoxylate, pyruvate, oxaloacetate or oxobutyrate
-
-
-
additional information
?
-
-
HpdR positively regulates hpdA expression through direct binding to the HpdA promoter within a region containing two conserved direct repeat sequences. HpdR-dependent hpdA transcription occurs in the presence of 4-hydroxyphenylpyruvate, tyrosine, and phenylalanine, as well as during starvation
-
-
-
additional information
?
-
-
Single turnover kinetics are observed spectrophotometrically by mixing equal volumes of the anaerobic enzyme-substrate complex and solutions containing molecular oxygen in the presence of saturating HPP using a stopped-flow spectrophotometer. k1 = 7.4 x 100000 /M/s, k2 = 74 /s, k3 = 13.2 /s, k4 = 1.6 /s, indicating the accumulation of three catalytic intermediates. The kinetic data observed with substrate substituted with deutererons for aromatic protons are not significantly different from those observed with the proteo substrate. The final phase in catalysis (k4), decreases to 0.7 /s in the presence of deuterium oxide solvent, indicating the involvement of a solvent-derived proton in this step.
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-hydroxyphenylpyruvate + O2
2,5-dihydroxyphenylacetate + CO2
P80064
-
-
-
?
additional information
?
-
-
HpdR positively regulates hpdA expression through direct binding to the HpdA promoter within a region containing two conserved direct repeat sequences. HpdR-dependent hpdA transcription occurs in the presence of 4-hydroxyphenylpyruvate, tyrosine, and phenylalanine, as well as during starvation
-
-
-
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
A7BG64
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme is involved in production of homogentisate, the aromatic precursor of all phenylquinones
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
key enzyme involved in tyrosine catabolism, congenital 4-hydroxyphenylpyruvate dioxygenase deficiency is a rare, relatively benign condition known as hereditary type III tyrosinemia
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
P32754
the conversion of 4-hydroxyphenyl-pyruvate to homogentisate involves oxidative decarboxylation, side-chain migration and aromatic hydroxylation in a single catalytic cycle. The 4-HPPD reaction is unusual in that the 2-oxoacid and prime substrate moieties are contained within the same molecule
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Q6KZ98
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Q6KZ98
second step of oxidative tyrosine catabolism
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Shewanella oneidensis MR-1 / ATCC 700550
Q8EKK9
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
Q53586
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
hppD is transcriptionally activated by HpdA and repressed by HpdR
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
enzyme participates in catabolism of tyrosine
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 85% homogentisate and 15% 4-hydroxyphenylacetate
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2 + 4-hydroxyphenylacetate
-
-
the wild-type enzyme produces 90% homogentisate, 1% quinolacetate, and 9% 4-hydroxyphenylacetate
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
copper
Fe
-
Fe(II), Fe(III), and Fe(IV) during oxygenation and hydroxylation, overview. The iron ion is coordinated by a His-His-Glu triad, structure of HPPD-Fe(II)-acetate complex, overview
Fe2+
Fe3+
Iron
copper
-
0.4 atoms of Fe per 89000 Da enzyme. Removal of copper does not correlate with loss of activity
Fe2+
-
in octahedral complex with His205, His287, Glu373 and three water molecules
Fe2+
-
required for activity, the active-site iron is in the ferric oxidation state and coordinated by the side chains of two histidines and on glutamate
Fe2+
-
the enol tautomer of 4-hydroxyphenylpyruvate appears to form a 2:1 complex with enzyme-bound Fe2+, the tautomerizable keto group with a double bond in 3-4 position favors productive substrate binding to Fe2+
Fe2+
-
a Fe(II)-dependent dioxygenase, Fe2+ is involved in the catalytic mechanism binding to the substrate, overview
Iron
-
iron-tyrosinate protein, high spin ferric center in a rhombic environment
Iron
-
one non-heme iron atom per monomer liganded to the sidechains of His161, His240, Glu322 and one acetate molecule
Iron
-
distorted square-pyramidal coordination with Glu349, His187, His270
Iron
-
0.9 atoms of Fe per 89000 Da enzyme. Removal of iron correlates with loss of activity
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,2-dihydroxybenzene-3,5-disulfonic acid
-
inhibition is prevented by ascorbate but not reversed by enol-4-hydroxyphenylpyruvate
1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
-
1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
-
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
binding mode
1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
-
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
binding mode
1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
-
1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
-
-
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
2,5-dihydroxyphenylacetic acid lactone
-
50% inhibition above 10 mM, competitive
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
-
-
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(2-chloro-4-methane sulfonylbenzoyl)-1,3-cyclohexanedione
competitive inhibitor
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(2-nitro-4-(trifluoromethyl)benzoyl)-1,3-cyclohexanedione
-
(NTBC), binding constant of 937 microM
2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione
-
NTBC, a commercial HPPD inhibitor in clinical use
-
2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
-
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
-
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
-
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
-
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
-
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
-
2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[2-nitro-4-(trifluoromethyl)benzoyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione
-
50 nM, 50% inhibition, tight-binding reversible inhibitor, rapid inactivation by the formation of an enzyme-inhibitor complex that dissociates extremely slowly with recovery of enzyme activity
2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
-
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
-
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
-
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione
-
-
-
3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
-
-
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
-
3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
-
3-(3,4-dichlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-bbromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(3-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-bromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
-
3-(4-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-(4-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
-
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
-
-
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
-
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
-
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
-
3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one
-
-
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
-
-
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-4-phenyl-2-furanone
-
0.0005 mM, 50% inhibition, may serve as a lead compound for further design of more potent inhibitors
3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
-
3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
-
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
-
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6-trimethyl-6-(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
-
4-(3-cyclohexylpropanoyl)-5-methoxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
-
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
-
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
-
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
-
5-hydroxy-2,2,6,6-tetramethyl-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
-
-
5-hydroxy-2,2,6,6-tetramethyl-4-(2-phenylacetyl)cyclohex-4-ene-1,3-dione
-
-
5-hydroxy-2,2,6,6-tetramethyl-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
-
-
5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione
-
-
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
binding mode
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
-
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
binding mode
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(3-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-phenylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(3-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
-
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
-
6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
-
6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
-
7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one
-
-
Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
pinocembrin
-
5,7-dihydroxyflavanone, isolation from Flourensia oolepis ethanol extract, inhibition mechanism. Pinocembrin is a reversible inhibitor of the enzyme and acts as a noncompetitive inhibitor, molecular modeling studies and binding mode, overview. Comparison to other HPPD enzyme-inhibitor complexes
tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
-
Urea
1 M, 3% inhibition. 3 M, 42% inhibition. 5 M, 56% inhibition
[1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone
-
50% inhibition at 12 nM
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
-
50% inhibition at 7 nM
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
50% inhibition below 20 nM
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
potent linear competitive inhibitor
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
rapid inactivation of the enzyme by the formation of an enzyme-inhibitor complex that dissociates with recovery of enzyme activity
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
-
is a selective and efficient herbicide that can be applied as a medicine in a hereditary metabolic disease - tyrosinemia type I
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
herbicide, drug to treat inborn defects of tyrosine catabolism, specifically type I tyrosinemia and alkaptonuria
2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione
-
mechanism of binding, enzyme-Fe(II)-inhibitor complex does not oxidize, dissociation rate constant is essentially zero
4-hydroxyphenylpyruvate
-
enzyme form 2 and 3, no substrate inhibition is observed for enzyme form 1
4-hydroxyphenylpyruvate
-
interaction of enol-4-hydroxyphenylpyruvate with enzyme-bound Fe3+, formed by autooxidation, causes the substrate inhibition
bathophenanthroline
-
0.018 mM, 50% inhibition; reactivation to 30% by dialysis and to 60% by addition to Fe2+
mesotrione
-
mesotrione is an extremely potent competitive inhibitor of this enzyme
mesotrione
-
molecular docking and molecular dynamics simulation estimate the interacting regions of HPPD with mesotrione using structure PDB ID 3ISQ
nitisinone
-
i.e. orfadin or NTBC, addition of NTBC halts the morphology transition and stems pathogenesis in this organism
-
nitisinone
-
i.e. orfadin or NTBC, bidentate coordination of NTBC with the HPPD active site ferrous ion, enzyme-bound crystal structure, overview
-
phenylpyruvate
-
non-competitive inhibition with 4-hydroxyphenylpyruvate as substrate
sulcotrione
for protein expressed in Escherichia coli DH5alpha (inhibition assayed without preincubation): 0 micoM sulcotrione = 100% activity, 0.5 microM sulcotrione = 58% activity left, 1.0 microM sulcotrione = 21.3% activity left, 1.5 microM sulcotrione = 2.8% activity left. Preincubation of the enzyme expressed in Escherichia coli SG13009 with sulcotrione for 15 min, significantly enhances the inhibition from 40% (1 microM sulcotrione/no preincubation) to 10% (1 microM sulcotrione/15 min preincubation).
additional information
-
high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis
-
additional information
-
efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
-
enzyme inhibition mechanisms and binding structures, molecular docking study, overview
-
additional information
-
design, synthesis and herbicidal activity of quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors with high herbicidal activity and improved cropselectivity, molecular dynamics simulations, structure-activity relationships, overview. Evaluation of herbicidal activity against against Echinochloa crus-galli, Setaria faberii, Digitaria sanguinalis, Amaranthus retroflexus, Eclipta prostrata, and Abutilon juncea
-
additional information
-
the enzyme is molecular target of new families of potent herbicides
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
structure-based design of a series of pyrazolone-quinazolone hybrids, as a class of human 4-hydroxyphenylpyruvate dioxygenase inhibitors, synthesis, overview. Molecular modeling indicates that the interaction between the pyrazolone ring and ferrous ion, and the hydrophobic interaction of quinazolone with its surrounding residues, such as Phe347 and Phe364, contribute greatly to the high potency of these inhibitors. Compounds N-(4-methoxyphenyl)-7-nitro-2,1,3-benzoxadiazol-4-amine and 3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one can be potentially useful for the treatment of type I tyrosinemia and other diseases with defects in tyrosine degradation
-
additional information
-
synthesis of pyrazole-benzimidazolone hybrids from DNS869 and droperidol, bioevaluation of pyrazole-benzimidazolone hybrids as human 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
[1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone, no significant inhibition up to 0.02 mM
-
additional information
-
enzyme inhibition mechanisms and binding structures, molecular docking study, overview
-
additional information
-
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
-
neither epoxybenzoaquinone ester nor 2-hydroxy-3-phenyl-3-butenoic acid is an inhibitor
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
glutathione
-
reducing cofactor required, either ascorbate, or a combination of 2,6-dichlorophenol indophenol and glutathione in presence of catalase
Trypsin
Frog
-
liver enzyme appears to be present in an inactive form which can be activated by treatment with trypsin or by autolysis
-
additional information
regarding expression and acitvity, rich or complex media (surplus of yeast extract, addition of glycerol and buffering of pH) are superior to media with less complex composition. Supplementation of media with FeSO4 or tyrosine does not substantially upgrade expression and activity levels.
-
2,6-dichlorophenol indophenol
-
reducing cofactor required, either ascorbate, or a combination of 2,6-dichlorophenol indophenol and glutathione
ascorbate
-
reducing cofactor required, either ascorbate, or a combination of 2,6-dichlorophenol indophenol and glutathione in presence of catalase
ascorbate
-
an optimized combination of ascorbate, 50 mM, catalase, 2.4 g/l, and iron, 0.05 mM, activates more than a combination of 2,6-dichlorophenolindophenol, glutathione and catalase
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.115
oxygen
-
activity is measured polarographically, assays include 0.5 microM of enzyme, 500 microM betaME, Fe2+ stoichiometric with enzyme, and 400 microM 4-hydroxyophenylpyruvate in 20 mM HEPES at pH 7.0 at 4°C
0.0069
4-hydroxyphenylpyruvate
-
activity is measured polarographically, assays include 0.5 microM of enzyme, 500 microM betaME, Fe2+ stoichiometric with enzyme, and 400 microM 4-hydroxyophenylpyruvate in 20 mM HEPES at pH 7.0 at 4°C
0.0075
4-hydroxyphenylpyruvate
-
recombinant wild-type enzyme, pH and temperature not specified in the publication
0.009
4-hydroxyphenylpyruvate
-
recombinant mutant S246A, pH and temperature not specified in the publication
0.027
4-hydroxyphenylpyruvate
-
pH 7.0, 25°C, wild-type enzyme and mutant N245I
0.08
4-hydroxyphenylpyruvate
-
pH 6.5, 37°C, wild-type enzyme and mutant DELTAG388
0.153
4-hydroxyphenylpyruvate
-
recombinant mutant N261D, pH and temperature not specified in the publication
0.286
4-hydroxyphenylpyruvate
-
recombinant mutant Q358E, pH and temperature not specified in the publication
0.452
4-hydroxyphenylpyruvate
-
recombinant mutant Q272E, pH and temperature not specified in the publication
0.551
4-hydroxyphenylpyruvate
-
recombinant mutant Q286E, pH and temperature not specified in the publication
11
4-hydroxyphenylpyruvate
-
Solvent is H2O. Steady-state analyses of 4-hydroxyphenylpyruvate dioxygenase using proteo-HPP, 2,3,5,6-tetradeutero-HPP, and proteo-HPP in deuterium oxide are carried out in 1 ml assays on a Hasetech oxygen electrode. The assay mixture include ferrous sulfate (10 microM), DTT (1mM), HPPD (500 nM), and HPP (0-1 mM) in 20 mM HEPES, pH (pD) 7.0, under conditions of atmospheric oxygen (350 microM at 5°C)
22
4-hydroxyphenylpyruvate
-
Solvent is H2O. Steady-state analyses of 4-hydroxyphenylpyruvate dioxygenase using proteo-HPP, 2,3,5,6-tetradeutero-HPP, and proteo-HPP in deuterium oxide are carried out in 1 ml assays on a Hasetech oxygen electrode. The assay mixture include ferrous sulfate (10 microM), DTT (1mM), HPPD (500 nM), and HPP (0-1 mM) in 20 mM HEPES, pH (pD) 7.0, under conditions of atmospheric oxygen (350 microM at 5°C)
54
4-hydroxyphenylpyruvate
-
Solvent is D2O. Steady-state analyses of 4-hydroxyphenylpyruvate dioxygenase using proteo-HPP, 2,3,5,6-tetradeutero-HPP, and proteo-HPP in deuterium oxide are carried out in 1 ml assays on a Hasetech oxygen electrode. The assay mixture include ferrous sulfate (10 microM), DTT (1mM), HPPD (500 nM), and HPP (0-1 mM) in 20 mM HEPES, pH (pD) 7.0, under conditions of atmospheric oxygen (350 microM at 5°C)
additional information
additional information
-
the Km-value is the same at 25°C and at 38°C
-
additional information
additional information
-
the Km-value is the same at 25°C and at 38°C
-
additional information
additional information
-
Kd value for 4-hydroxyphenylpyruvate with 4-hydroxyphenylpyruvate dioxygenase Fe2+ is 29 microM, whereas the binding constant for phenylpyruvate is determined to be 319 microM
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.065
4-hydroxyphenylpyruvate
-
activity is measured polarographically, assays include 0.5 microM of enzyme, 500 microM betaME, Fe2+ stoichiometric with enzyme, and 400 microM 4-hydroxyophenylpyruvate in 20 mM HEPES at pH 7.0 at 4°C
0.1
4-hydroxyphenylpyruvate
-
recombinant mutant Q286E, pH and temperature not specified in the publication
0.2
4-hydroxyphenylpyruvate
-
recombinant mutant Q272E, pH and temperature not specified in the publication; recombinant mutant S246A, pH and temperature not specified in the publication
0.3
4-hydroxyphenylpyruvate
-
recombinant mutant N261D, pH and temperature not specified in the publication
1.8
4-hydroxyphenylpyruvate
-
recombinant wild-type enzyme, pH and temperature not specified in the publication
2.1
4-hydroxyphenylpyruvate
-
recombinant mutant Q358E, pH and temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000458
1-benzyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000355
1-benzyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000028
1-butyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000019
1-butyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
1-ethyl-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000047
1-ethyl-6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000005
1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000203 - 0.000327
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
0.000139
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000082
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000029
2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000304
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000076
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0000098
2-(2-chloro-4-methanesulfonylbenzoyl)-1,3-cyclohexanedione
-
-
0.000025
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000017
2-(5-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021 - 0.000055
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
0.000014
2-(6-chloro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
2-(6-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000222
2-(6-ethyl-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
2-(6-fluoro-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000041
2-(7-bromo-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000291
2-(7-chloro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000072
2-(7-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000626
2-(7-fluoro-2-methoxy-6-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
2-(8-chloro-2-methoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000113
2-[(2,3-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000088
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
-
0.000066
2-[(2,4-dibromophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000242
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.004803
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000197
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000043
2-[(2,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000121
2-[(2,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
2-[(2,6-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
2-[(2-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002141
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001143
2-[(2-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000267
2-[(3,4-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000956
2-[(3,5-dichlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000075
2-[(3-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000078
2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000351
2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002001
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-4,4-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00011
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000037
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxy-5-methylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000031
2-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000029
2-[(4-chlorophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000213
2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000189
2-[[(1-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00393
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002831
2-[[(5-bromonaphthalen-2-yl)oxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000369
2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000161
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000059
3-(2,4-dimethylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000087
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000011
3-(2-bromo-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
3-(2-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000109
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00009
3-(2-chloro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
3-(2-chlorophenyl)-1-ethyl-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
-
0.000023
3-(2-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
3-(2-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000086
3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-(2-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000081
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00017
3-(2-fluoro-4-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000079
3-(2-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
3-(2-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000008
3-(2-hydroxy-5-methyl-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-8-methylquinoline-2-carbonitrile
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000025
3-(3,4-dichlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000093
3-(3-bbromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000014
3-(3-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000033
3-(3-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000027
3-(3-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000173
3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00001
3-(3-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00009
3-(3-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00002
3-(3-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
3-(4-bromophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000018
3-(4-bromophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000177
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000032
3-(4-chloro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000115
3-(4-chlorophenyl)-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000023
3-(4-chlorophenyl)-6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000237
3-(4-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-(4-chlorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000219
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00004
3-(4-fluoro-2-methylphenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000247
3-(4-fluorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
3-(4-fluorophenyl)-6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-hydroxy-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000016
3-hydroxy-2-(2-methoxy-5,6-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000028
3-hydroxy-2-(2-methoxy-5,7-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
3-hydroxy-2-(2-methoxy-5,8-dimethylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000009
3-hydroxy-2-(2-methoxy-5-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000074
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-5,5-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000298
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000099
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)-6-methylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
3-hydroxy-2-(2-methoxy-6-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00003
3-hydroxy-2-(2-methoxy-7-methylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000341
3-hydroxy-2-(2-methoxy-7-sulfanylquinoline-3-carbonyl)-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000062
3-hydroxy-2-(2-methoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000171
3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001243
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000075
3-hydroxy-2-(quinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000184
3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000077
3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000894
3-hydroxy-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000045
3-hydroxy-2-[(2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000623
3-hydroxy-2-[(3-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000301
3-hydroxy-2-[(4-methoxyphenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000069
3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000988
3-hydroxy-2-[(4-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
3-hydroxy-2-[(pentafluorophenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000035
3-hydroxy-2-[2-methoxy-5-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000009
3-hydroxy-2-[2-methoxy-6-(methylsulfanyl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000132
3-hydroxy-2-[2-methoxy-6-(propan-2-yl)quinoline-3-carbonyl]-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00002
3-hydroxy-2-[8-methyl-2-(trifluoromethyl)quinoline-3-carbonyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000215
3-hydroxy-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000253
3-hydroxy-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000598
3-hydroxy-2-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000134
3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000561
3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000544
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000354
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001052
3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001133
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000079
3-hydroxy-4,4-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.005571
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001596
3-hydroxy-5,5-dimethyl-2-[(2-methylphenoxy)acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003556
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003662
3-hydroxy-5,5-dimethyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.001298
3-hydroxy-5-methyl-2-[[(naphthalen-1-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003615
3-hydroxy-5-methyl-2-[[(naphthalen-2-yl)oxy]acetyl]cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000007
3-hydroxy-6-methyl-2-(2,5,8-trimethylquinoline-3-carbonyl)cyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000112
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000408
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000245
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000038
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000054
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000043
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000668
6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000024
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000067
6-(2-hydroxy-4-methyl-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000042
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(3-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000032
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-methyl-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000141
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000017
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(2-methylpropyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000033
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-(prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000015
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)-1-propylquinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000627
6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000074
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000248
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000156
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000207
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000238
6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000031
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(3-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00016
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-(4-(trifluoromethoxy)phenyl) quinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000013
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-m-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000058
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-o-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000025
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-p-tolylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000019
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-3-phenylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000038
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(2-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000034
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(3-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00006
6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.002335
6-[2-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000815
6-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]naphthalene-1-carbonitrile
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.003152
7-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]-2H-1-benzopyran-2-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000203
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000327
1-[(2-fluorophenyl)methyl]-6-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-ene-1-carbonyl)-3-(4-methylphenyl)quinazoline-2,4(1H,3H)-dione
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000055
2-(6-bromo-2-methoxy-5-methylquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000208
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000547
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000013
mesotrione
-
pH 7.0, 30°C, recombinant His-tagged enzyme
0.000068 - 0.0236
mesotrione
-
dependent on the system used, overview. pH and temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00094
1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000021
1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00064
1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00017
1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00093
1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00013
1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00022
1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00097
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00074
1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000039
1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00015
1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00099
1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00068
2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione
Homo sapiens
-
pH 7.0, 30°C, recombinant His-tagged enzyme
-
0.00097
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00088
3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000064
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000022
3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00675
4-(2,4-dichlorobenzyl)-1,3-dimethyl-5-hydroxypyrazole
Coptis japonica var. dissecta
A7BG64
recombinant enzyme
0.00017
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00227
4-(3-cyclohexylpropanoyl)-5-hydroxy-2,2,6-trimethyl-6-(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00041
4-(3-cyclohexylpropanoyl)-5-methoxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.000019
4-decanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00025
4-dodecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00096
4-hexanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00072
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00271
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00094
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
-
0.00119
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00099
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00103
5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00004
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
-
0.00014
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000061
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000077
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00025
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000059
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0143
5-hydroxy-2,2,6,6-tetramethyl-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.0189
5-hydroxy-2,2,6,6-tetramethyl-4-(2-phenylacetyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.0118
5-hydroxy-2,2,6,6-tetramethyl-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.00075
5-hydroxy-2,2,6,6-tetramethyl-4-(3-phenylpropanoyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
grandiflorone, most active naturally occurring beta-triketone
0.00031
5-hydroxy-2,2,6,6-tetramethyl-4-palmitoylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.0445
5-hydroxy-4-isobutyryl-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
-
0.0001
Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.00067
enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000027
mesotrione
Arabidopsis thaliana
-
pH and temperature not specified in the publication
0.000022
sulcotrione
Arabidopsis thaliana
-
pH and temperature not specified in the publication
0.0001
tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
Homo sapiens
-
recombinant His-tagged enzyme, pH 7.0, 30°C
0.000012
DAS 645
Arabidopsis thaliana
-
pH and temperature not specified in the publication
-
0.00002