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Information on EC 1.13.11.27 - 4-hydroxyphenylpyruvate dioxygenase and Organism(s) Arabidopsis thaliana and UniProt Accession P93836
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1.13.11.27 4-hydroxyphenylpyruvate dioxygenaseIUBMB Comments
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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Word Map
- 1.13.11.27
-
syncytial
- viruses
- newcastle
- hn
- paramyxovirus
- epitope
- hemagglutinin-neuraminidase
- infant
- measles
- parainfluenza
-
herbicide
-
sendai
- homogentisate
-
heptad
- hemagglutinin
- virion
-
fusogenic
- tyrosinemia
- metapneumovirus
-
prefusion
-
anti-f
-
palivizumab
-
weed
-
postfusion
- paramyxoviridae
- furin
- distemper
- ectodomains
- mumps
-
virus-cell
-
rsv-infected
-
six-helix
-
cleavability
-
formalin-inactivated
-
lasota
-
virus-neutralizing
-
virus-like
- morbillivirus
- panencephalitis
- ntbc
-
anti-rsv
-
nipah
-
velogenic
- nucleopolyhedrovirus
- drug development
- alkaptonuria
- diagnostics
-
thomsen-friedenreich
- agriculture
- environmental protection
- rinderpest
-
live-attenuated
- medicine
-
merger
- fumarylacetoacetate
The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
f protein, 4-hydroxyphenylpyruvate dioxygenase, tf-ag, p-hydroxyphenylpyruvate dioxygenase, 4-hppd, 4-hydroxyphenylpyruvic acid dioxygenase, athppd, 4hppd, legiolysin, p-hydroxyphenylpyruvate hydroxylase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
HPPD
-
4-HPPD
-
-
-
-
4-hydroxyphenylpyruvic acid dioxygenase
-
-
-
-
4HPPD
-
-
-
-
EC 1.14.2.2
-
-
-
-
EC 1.99.1.14, formerly
-
-
-
-
F Alloantigen
-
-
-
-
F protein
-
-
-
-
F-antigen homolog
-
-
-
-
HPD
-
-
-
-
HPPD
HPPDase
-
-
-
-
Legiolysin
-
-
-
-
oxygenase, 4-hydroxyphenylpyruvate di-
-
-
-
-
p-hydroxyphenylpyruvate dioxygenase
-
-
-
-
p-hydroxyphenylpyruvate hydroxylase
-
-
-
-
p-hydroxyphenylpyruvate oxidase
-
-
-
-
p-hydroxyphenylpyruvic acid hydroxylase
-
-
-
-
p-hydroxyphenylpyruvic hydroxylase
-
-
-
-
p-hydroxyphenylpyruvic oxidase
-
-
-
-
T-cell reactive protein
-
-
-
-
TF-AG
-
-
-
-
HPPD
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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 and molecular mechanics (QM/MM) combined with coupling techniques and molecular dynamics, overview
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
direct involvement of the arene oxide intermediate to the reaction mechanism
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
-
-
-
-
redox reaction
-
-
-
-
hydroxylation
-
-
-
-
side-chain migration
-
-
-
-
PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
-
-, -, -, -
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.
CAS REGISTRY NUMBER
COMMENTARY
9029-72-5
-
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
homogentisate + 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
-
-
?
NATURAL SUBSTRATE
NATURAL 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
homogentisate + CO2
-
-
-
?
4-hydroxyphenylpyruvate + O2
homogentisate + CO2
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Fe2+
in octahedral complex with His205, His287, Glu373 and three water molecules
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5,7-dichlorobenzofuran-2-yl)methanone
-
-
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5-nitrobenzofuran-2-yl)methanone
compound displays excellent herbicidal activity
-
(5,7-dichlorobenzofuran-2-yl)(5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanone
compound displays excellent herbicidal activity
-
1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
50% inhibition at 7 nM
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-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-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-[(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
-
2,6-difluoro-4-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-2-oxoethoxy]benzonitrile
-
2-(2,6-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxy-6,6-dimethylcyclohex-2-en-1-one
-
2-(2,7-dimethoxyquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
2-(5,7-dichlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
2-(5-chlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
-
-
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-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
showed the highest HPPD inhibitory activity of the compounds tested
-
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-chloro-4-nitrophenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(2-chlorophenoxy)acetyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
-
2-[(2-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(3-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-bromo-2-fluorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-bromo-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chloro-2-fluorophenoxy)acetyl]-3-hydroxycyclohex-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-[(4-chloro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[(4-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
-
-
2-[(4-fluoro-2-methylphenoxy)acetyl]-3-hydroxycyclohex-2-en-1-one
-
2-[2-(benzyloxy)-5-methylquinoline-3-carbonyl]-3-hydroxycyclohex-2-en-1-one
-
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
-
2-[[4-(4-chlorobenzoyl)phenoxy]acetyl]-3-hydroxycyclohex-2-en-1-one
-
3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione
competitive inhibitor with respect to HPPA with the characteristic of slow binding and lower potency against human enzyme
-
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-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
-
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-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-(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-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-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-(3,5,6-trichloro-4-((4-chlorobenzyl)amino)picolinoyl)cyclohex-2-en-1-one
compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment and show superior weed-controlling efficacy against Setaria viridis
-
3-hydroxy-2-(3,5,6-trichloro-4-((4-isopropylbenzyl)amino)picolinoyl)cyclohex-2-en-1-one
an additional pi-pi stacking interaction with Phe-392 and hydrophobic contacts with Met335 and Pro384 are detected in AtHPPD upon the binding. Compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment
-
3-hydroxy-2-(3,5,6-trichloro-4-((4-methylbenzyl)amino)-picolinoyl)cyclohex-2-en-1-one
compound displays excellent greenhouse herbicidal effects at 150 g of active ingredient/ha after postemergence treatment
-
3-hydroxy-2-(5-methyl-2-propoxyquinoline-3-carbonyl)cyclohex-2-en-1-one
-
3-hydroxy-2-(5-nitrobenzofuran-2-carbonyl)cyclohex-2-en-1-one
-
-
3-hydroxy-2-[(2,4,6-trichlorophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(2-methyl-4-nitrophenoxy)acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[(4-methyl-2-nitrophenoxy)acetyl]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-[[2-(methylsulfanyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[2-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[3-(trifluoromethyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]-5-methylcyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(methanesulfonyl)phenoxy]acetyl]cyclohex-2-en-1-one
-
3-hydroxy-2-[[4-(trifluoromethyl)phenoxy]acetyl]cyclohex-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-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
-
3-[(2E)-3-(2-bromo-5-hydroxyphenyl)prop-2-enoyl]-4-hydroxy-6-methyl-2H-pyran-2-one
compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme
-
3-[2-chloro-4-(methanesulfonyl)benzoyl]-1,3-oxazolidin-2-one
compound forms a stable bidentate interaction with the active center CoII chelation. The benzene ring is sandwiched by the phenyl rings of residues Phe381 and Phe424. The compound shows good herbicidal activities against tested weeds Echinochloa crus-galli and Abutilon juncea
-
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-decanoyl-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
-
4-dodecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-hexanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
-
4-hydroxy-3-[(2E)-3-(3-iodophenyl)prop-2-enoyl]-6-methyl-2H-pyran-2-one
compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme
-
4-hydroxy-3-[(2E)-3-(3-methoxyphenyl)prop-2-enoyl]-6-methyl-2H-pyran-2-one
compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme
-
4-hydroxy-6-methyl-3-[(2E)-3-phenylprop-2-enoyl]-2H-pyran-2-one
compound generates bidentate coordination with Fe(II) and forms sandwiched pi-pi interaction of the benzene ring with Phe403 and Phe360 and pi-pi stacking interactions with Phe398 of the enzyme
-
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-[(3-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione
-
-
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-2,2,6,6-tetramethyl-4-palmitoylcyclohex-4-ene-1,3-dione
-
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
-
5-hydroxy-4-isobutyryl-2,2,6,6-tetramethylcyclohex-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-[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
-
[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-(2-chloropyridin-3-yl)-2-(2-oxo-1,3-oxazolidin-3-yl)ethane-1,2-dione
-
-
1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
1-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]pyrrolidine-2,5-dione
-
-
2-(2-nitro-4-(trifluoromethyl)benzoyl)-1,3-cyclohexanedione
-
(NTBC), binding constant of 937 microM
2-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
2-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1H-isoindole-1,3(2H)-dione
-
-
3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-oxazolidin-2-one
-
-
3-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)carbonyl]-1,3-thiazolidin-2-one
-
-
3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-oxazolidin-2-one
-
-
3-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl]-1,3-thiazolidin-2-one
-
-
methyl 3-chloro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate
-
-
methyl 3-nitro-4-[(2-oxo-1,3-oxazolidin-3-yl)carbonyl]benzenesulfinate
-
-
methyl 3-nitro-4-[(2-oxo-1,3-thiazolidin-3-yl)carbonyl]benzenesulfinate
-
-
3-hydroxy-2-(phenoxyacetyl)cyclohex-2-en-1-one
binding free energy -19.81 kcal/mol, residue groups including Val207, Leu244, His287, Ala289, Phe371, Glu373, Lys400, and Phe403 participate in the binding
3-hydroxy-5,5-dimethyl-2-(phenoxyacetyl)cyclohex-2-en-1-one
binding free energy -3.65 kcal/mol, residue groups including Val207, Leu244, Pro259, Asn261, His287, Phe360, and Phe403 participate in the binding
mesotrione
mesotrione is an extremely potent competitive inhibitor of this enzyme
mesotrione
binding free energy -28.34 kcal/mol, residues Val207, Leu244, Leu347, Phe398, Gly399, Phe403, and Phe407 make the greatest contribution to the binding energy
mesotrione
slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
nitisinone
i.e. 2-[2-nitro-4-(trifluoromethyl) benzoyl]-1,3-cyclohexanedione, slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
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).
sulcotrione
slow binding inhibitor, not inhibitory to homogentisate 1,2-dioxygenase
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
design, synthesis, and herbicidal activity of triketone-quinoline hybrids as 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview. Computational modeling and CoMSIA analysis
-
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
-
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
high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors
-
additional information
inhibition mechanism of enzyme HPPD, detailed overview
-
additional information
in silico analization of 2-(aryloxyacetyl)cyclohexane-1,3-diones derivatives as valid HPPD inhibitors
-
additional information
in silico structure-based virtual screening of four commercial databases to find inhibitors
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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.
-
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.
-
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
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
-
0.098
4-hydroxyphenylpyruvate
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7,20°C
0.134
4-hydroxyphenylpyruvate
mutant M335H/P336A/E363Q, pH 7,20°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
0.153
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
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.116
4-hydroxyphenylpyruvate
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7,20°C
0.177
4-hydroxyphenylpyruvate
mutant M335H/P336A/E363Q, pH 7,20°C
8.25
4-hydroxyphenylpyruvate
mutant P315R/R328A/L347M, pH 7, 25°C
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
0.2
4-hydroxyphenylpyruvate
-
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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000102
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5,7-dichlorobenzofuran-2-yl)methanone
30°C, pH not specified in the publication
-
0.000099
(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)(5-nitrobenzofuran-2-yl)methanone
30°C, pH not specified in the publication
-
0.000223
(5,7-dichlorobenzofuran-2-yl)(5-hydroxy-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanone
30°C, pH not specified in the publication
-
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
0.000025
2-(2-ethoxy-5-methylquinoline-3-carbonyl)-3-hydroxycyclohex-2-en-1-one
recombinant His-tagged enzyme, pH 7.0, 30°C
0.0001
2-(5,7-dichlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
30°C, pH not specified in the publication
-
0.000074
2-(5-chlorobenzofuran-2-carbonyl)-3-hydroxycyclohex-2-en-1-one
30°C, pH not specified in the publication
-
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
0.0000039
2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
pH not specified in the publication, 25°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
0.0000242
3-(2,6-dimethylphenyl)-1-methyl-6-(2-oxidanyl-6-oxidanylidene-cyclohexen-1-yl)carbonyl-quinazoline-2,4-dione
pH 7, 25°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
0.000008
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
0.000033
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
0.000115
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
0.000007
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
0.000095
3-hydroxy-2-(5-nitrobenzofuran-2-carbonyl)cyclohex-2-en-1-one
30°C, pH not specified in the publication
-
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
0.002335
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
0.0000044
pyrasulfotole
pH not specified in the publication, 25°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
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00009
2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00011
2-[(2-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.0001
2-[(3-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00011
2-[(4-bromo-2-fluorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.00012
2-[(4-chlorophenyl)methyl]-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°C
-
0.000273
3-hydroxy-2-(3,5,6-trichloro-4-((4-chlorobenzyl)amino)picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.000047
3-hydroxy-2-(3,5,6-trichloro-4-((4-isopropylbenzyl)amino)picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.000077
3-hydroxy-2-(3,5,6-trichloro-4-((4-methylbenzyl)amino)-picolinoyl)cyclohex-2-en-1-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
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
-
0.00249
4-hydroxy-6-methyl-3-[(2E)-3-phenylprop-2-enoyl]-2H-pyran-2-one
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
-
0.0001
5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-[(3-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione
Arabidopsis thaliana
pH not specified in the publication, 25°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
-
0.000012
DAS 645
Arabidopsis thaliana
pH and temperature not specified in the publication
0.000043
bicyclopyrone
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.0000075
isoxaflutole
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.0000068
mesotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000027
mesotrione
Arabidopsis thaliana
pH and temperature not specified in the publication
0.000273
mesotrione
Arabidopsis thaliana
pH not specified in the publication, temperature not specified in the publication
0.000012
sulcotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.000022
sulcotrione
Arabidopsis thaliana
pH and temperature not specified in the publication
0.00001
tembotrione
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
0.0000061
topramezone
Arabidopsis thaliana
mutant M335H/P336A/P339T/T341D/E363Q/E426Q, pH 7, 20°C
additional information
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3,3,5,5-tetramethyl-2,4,6-trioxocyclohexyl 3-methylbutanoate
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3-(2-cyclohexylethyl)-5,5,7,7-tetramethylbenzo[d]isoxazole-4,6(5H,7H)-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
Arabidopsis thaliana
IC50 value above 50 microM
additional information
3-cyclohexyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-enyl)phenyl)propan-1-one
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-(cyclohexanecarbonyl)-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-acetyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
4-dodecanoyl-5-hydroxy-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
additional information
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
IC50 value above 50 microM
additional information
5-hydroxy-4-isobutyryl-2,2,6,6-tetrakis(3-methylbut-2-enyl)cyclohex-4-ene-1,3-dione
Arabidopsis thaliana
-
IC50 value above 50 microM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
activity of 0.0033 micromol/min/mg for 2YT-grown Escherichia coli DH5alpha extract and 0.0018 micromol/min/mg for LB-grown Escherichia coli DH5alpha
additional information
-
activity of 0.0033 micromol/min/mg for 2YT-grown Escherichia coli DH5alpha extract and 0.0018 micromol/min/mg for LB-grown Escherichia coli DH5alpha
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
658016, 704130, 741741, 741762, 742725, 742731, 743211, 743407, 764655, 764723, 764724, 764949, 764950, 764963, 765504, 765506, 765723, 765756
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
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
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
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
additional information
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
-
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). HPPD_ARATH
445
0
48816
Swiss-Prot
other Location (Reliability: 4)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
a ligand-mediated conformational switch in helix H11 mediates rapid substrate access followed by active site closing and efficient product release through H11 opening. In mutant HPPD, large differences in H11 gating are found with correlation to experimentally measured herbicide tolerance
structure in complex with inhibitor 2-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-isoindole-1,3(2H)-dione at a resolution of 1.8 A. The two carbonyl groups of 2-benzoylethen-1-ol formed a bidentate chelating interaction with the metal ion, while the isoindoline-1,3-dione moiety formes pronounced pi-pi stacking interactions with Phe381 and Phe424
structure of HPPD in complex with substrate 4-hydroxyphenylpyruvate at a resolution of 2.80 A. 4-Hydroxyphenylpyruvate takes keto rather than enol form inside the HPPD active pocket. Residues Phe424, Asn423, Glu394, Gln307, Asn282, and Ser267 play important roles in substrate binding and catalytic cycle. Residue Gln293 undergoes a rotation upon the HPPA binding and forms H-bond network of Ser267-Asn282-Gln307-Gln293, resulting in the transformation of HPPD from an inactive state to active state
structures in complex with inhibitors nitisinone, sulcotrione and mesotrione. A conformational change of Phe428 is found at the C-terminal alpha-helix in the inhibitor-bound structures and the inhibition kinetics of drugs are related to steric hindrance of Phe428
with and without inhibitors [1-tert-butyl-3-(2,4-dichlorophenyl)-5-hydroxy-1H-pyrazol-4-yl][2-chloro-4-(methylsulfonyl)phenyl]methanone or 1-(1,1-dimethylethyl)-5-hydroxy-4-(3-(4-(methoxy)phenyl)-2-methyl-4-(methylsulfonyl)benzoyl)pyrazole
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
M335H/P336A/E363Q
residues 336 and 363 are substituted by the corresponding residues of Zea mays HPPD, more than twofold increase in IC50 for sulcotrione and tembotrione. Increased herbicide tolerance compared to wild-type matches with a clear shift in the free energy profile toward favoring the closed helix H11 state
M335H/P336A/P339T/T341D/E363Q/E426Q
substitutions correspond to residues found in Zea mays. The mutant has a clear preference for the closed H11 state
P315R/R328A/L347M
mutations induce an 8fold increase in the value of k4 in respect of mesotrione
N261D
-
site-directed mutagenesis, during the reaction mechanism, the last 1,2 rearrangement is blocked in S246A HPPD mutant, so that an arene oxide-derived intermediate is released as an alternative product, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
Q272E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
Q286E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
Q358E
-
site-directed mutagenesis, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
S246A
-
site-directed mutagenesis, during the reaction mechanism, the last 1,2 rearrangement is blocked in S246A HPPD mutant, so that an arene oxide-derived intermediate is released as an alternative product, the mutant shows increased Km and reduced kcat for 4-hydroxyphenylpyruvate compared to the wild-type enzyme
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
regeneration of time-dependent inactivated 4-hydroxyphenylpyruvate dioxygenase by incubation with ascorbic acid and/or Fe2+ salts is not successful
the enzyme is stable for several hours at room temperature, indefinitely at 4°C
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
storage at room temperature results in residual enzyme activities of ca. 60-80% after 16 h or 40-50% after 30 h.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration
recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration
-
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Eschrichia coli stains DH5alpha, M15(pRep4) or SG13009
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
gene HPD, recombinant expression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3), subcloning in Escherichia coli strain DH5alpha, determination of protein expression patterns
overexpression of Arabidopsis thaliana p-hydroxyphenylpyruvate dioxygenase and Arabidopsis thaliana homogentisate phytyltransferase in Solanum tuberosum. Over-expression of At-HPPD results in a maximum 266% increase in alpha-tocopherol, and over-expression of At-HPT yields a 106% increase. Tubers from transgenic plants accumulate approximately 10fold and 100fold less a-tocopherol than leaves or seeds, respectively
-
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
-
gene HPD, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
drug development
agriculture
4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery
agriculture
plant 4-hydroxyphenylpyruvate dioxygenase (HPPD) is the molecular target of a range of commercial synthetic beta-triketone herbicides Their mode of action is based on an irreversible inhibition of HPPD
agriculture
the enzyme is a target for herbicides, e.g. triketone inhibitors
drug development
4-hydroxyphenylpyruvate dioxygenase is one of the most promising target sites for herbicide discovery
drug development
plant 4-hydroxyphenylpyruvate dioxygenase (HPPD) is the molecular target for development of specific inhibitors
drug development
the enzyme is a target for inhibitor and herbicide development
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yang, C.; Pflugrath, J.W.; Camper, D.L.; Foster, M.L.; Pernich, D.J.; Walsh, T.A.
Structural basis for herbicidal inhibitor selectivity revealed by comparison of crystal structures of plant and mammalian 4-hydroxyphenylpyruvate dioxygenases
Biochemistry
43
10414-10423
2004
Rattus norvegicus (P32755), Arabidopsis thaliana (P93836), Arabidopsis thaliana
Fritze, I.M.; Linden, L.; Freigang, J.; Auerbach, G.; Huber, R.; Steinbacher, S.
The crystal structures of Zea mays and Arabidopsis 4-hydroxyphenylpyruvate dioxygenase
Plant Physiol.
134
1388-1400
2004
Arabidopsis thaliana, Zea mays
Purpero, V.M.; Moran, G.R.
Catalytic, noncatalytic, and inhibitory phenomena: kinetic analysis of (4-hydroxyphenyl)pyruvate dioxygenase from Arabidopsis thaliana
Biochemistry
45
6044-6055
2006
Arabidopsis thaliana
Lederer, B.; Boeger, P.
Recombinant p-hydroxyphenylpyruvate dioxygenase of high activity
Z. Naturforsch. C
60
549-556
2005
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Dayan, F.E.; Duke, S.O.; Sauldubois, A.; Singh, N.; McCurdy, C.; Cantrell, C.
p-Hydroxyphenylpyruvate dioxygenase is a herbicidal target site for beta-triketones from Leptospermum scoparium
Phytochemistry
68
2004-2014
2007
Arabidopsis thaliana (P93836)
Crowell, E.F.; McGrath, J.M.; Douches, D.S.
Accumulation of vitamin E in potato (Solanum tuberosum) tubers
Transgenic Res.
17
205-217
2008
Arabidopsis thaliana
Dayan, F.E.; Singh, N.; McCurdy, C.R.; Godfrey, C.A.; Larsen, L.; Weavers, R.T.; Van Klink, J.W.; Perry, N.B.
Beta-triketone inhibitors of plant p-hydroxyphenylpyruvate dioxygenase: modeling and comparative molecular field analysis of their interactions
J. Agric. Food Chem.
57
5194-5200
2009
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Raspail, C.; Graindorge, M.; Moreau, Y.; Crouzy, S.; Lefebvre, B.; Robin, A.Y.; Dumas, R.; Matringe, M.
4-hydroxyphenylpyruvate dioxygenase catalysis: identification of catalytic residues and production of a hydroxylated intermediate shared with a structurally unrelated enzyme
J. Biol. Chem.
286
26061-26070
2011
Arabidopsis thaliana, Daucus carota, Pseudomonas fluorescens, Streptomyces avermitilis
Rocaboy-Faquet, E.; Noguer, T.; Romdhane, S.; Bertrand, C.; Dayan, F.E.; Barthelmebs, L.
Novel bacterial bioassay for a high-throughput screening of 4-hydroxyphenylpyruvate dioxygenase inhibitors
Appl. Microbiol. Biotechnol.
98
7243-7252
2014
Arabidopsis thaliana (P93836)
Moran, G.
4-Hydroxyphenylpyruvate dioxygenase and hydroxymandelate synthase exemplars of the alpha-keto acid dependent oxygenases
Arch. Biochem. Biophys.
544
58-68
2014
Pseudomonas fluorescens, Paracoccidioides brasiliensis, Homo sapiens (P32754), Arabidopsis thaliana (P93836), Streptomyces avermitilis (Q53586), Streptomyces avermitilis ATCC 31267 (Q53586)
Wang, D.W.; Lin, H.Y.; Cao, R.J.; Chen, T.; Wu, F.X.; Hao, G.F.; Chen, Q.; Yang, W.C.; Yang, G.F.
Synthesis and herbicidal activity of triketone-quinoline hybrids as novel 4-hydroxyphenylpyruvate dioxygenase inhibitors
J. Agric. Food Chem.
63
5587-5596
2015
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Wang, D.W.; Lin, H.Y.; He, B.; Wu, F.X.; Chen, T.; Chen, Q.; Yang, W.C.; Yang, G.F.
An efficient one-pot synthesis of 2-(aryloxyacetyl)cyclohexane-1,3-diones as herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors
J. Agric. Food Chem.
64
8986-8993
2016
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Silva, T.; Dos Santos Pires, M.; De Castro, A.; Da Cunha, E.; Caetano, M.; Ramalho, T.
Molecular insight into the inhibition mechanism of plant and rat 4-hydroxyphenylpyruvate dioxygenase by molecular docking and DFT calculations
Med. Chem. Res.
24
3958-3971
2015
Rattus norvegicus (P32755), Arabidopsis thaliana (P93836)
-
Wang, D.W.; Lin, H.Y.; Cao, R.J.; Ming, Z.Z.; Chen, T.; Hao, G.F.; Yang, W.C.; Yang, G.F.
Design, synthesis and herbicidal activity of novel quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors
Pest Manag. Sci.
71
1122-1132
2015
Arabidopsis thaliana (P93836)
Lin, H.Y.; Yang, J.F.; Wang, D.W.; Hao, G.F.; Dong, J.Q.; Wang, Y.X.; Yang, W.C.; Wu, J.W.; Zhan, C.G.; Yang, G.F.
Molecular insights into the mechanism of 4-hydroxyphenylpyruvate dioxygenase inhibition enzyme kinetics, X-ray crystallography and computational simulations
FEBS J.
286
975-990
2019
Arabidopsis thaliana (P93836)
Fu, Y.; Sun, Y.N.; Yi, K.H.; Li, M.Q.; Cao, H.F.; Li, J.Z.; Ye, F.
Combination of virtual screening protocol by in silico toward the discovery of novel 4-hydroxyphenylpyruvate dioxygenase inhibitors
Front. Chem.
6
14
2018
Arabidopsis thaliana (P93836)
Fu, Y.; Liu, Y.X.; Yi, K.H.; Li, M.Q.; Li, J.Z.; Ye, F.
Quantitative structure activity relationship studies and molecular dynamics simulations of 2-(aryloxyacetyl)cyclohexane-1,3-diones derivatives as 4-hydroxyphenylpyruvate dioxygenase inhibitors
Front. Chem.
7
556
2019
Arabidopsis thaliana (P93836)
He, B.; Dong, J.; Lin, H.; Wang, M.; Li, X.; Zheng, B.; Chen, Q.; Hao, G.; Yang, W.; Yang, G.
Pyrazole-isoindoline-1,3-dione hybrid A promising scaffold for 4-hydroxyphenylpyruvate dioxygenase inhibitors
J. Agric. Food Chem.
67
10844-10852
2019
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Fu, Y.; Zhang, D.; Zhang, S.Q.; Liu, Y.X.; Guo, Y.Y.; Wang, M.X.; Gao, S.; Zhao, L.X.; Ye, F.
Discovery of N-aroyl diketone/triketone derivatives as novel 4-hydroxyphenylpyruvate dioxygenase inhibiting-based herbicides
J. Agric. Food Chem.
67
11839-11847
2019
Arabidopsis thaliana, Arabidopsis thaliana (P93836)
Nan, J.X.; Yang, J.F.; Lin, H.Y.; Yan, Y.C.; Zhou, S.M.; Wei, X.F.; Chen, Q.; Yang, W.C.; Qu, R.Y.; Yang, G.F.
Synthesis and herbicidal activity of triketone-aminopyridines as potent p-hydroxyphenylpyruvate dioxygenase inhibitors
J. Agric. Food Chem.
69
5734-5745
2021
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Huang, H.; Zhang, J.Q.; Liu, J.M.; Wang, M.M.; Shu, L.; Yan, Y.L.; Zhan, X.H.; Wang, P.; Huan, X.T.; Zhang, D.Y.
Discovery of novel benzofuran scaffold as 4-hydroxyphenylpyruvate dioxygenase inhibitors
Pest Manag. Sci.
77
1409-1421
2021
Arabidopsis thaliana (P93836), Arabidopsis thaliana
Hawkes, T.R.; Langford, M.P.; Viner, R.; Blain, R.E.; Callaghan, F.M.; Mackay, E.A.; Hogg, B.V.; Singh, S.; Dale, R.P.
Characterization of 4-hydroxyphenylpyruvate dioxygenases, inhibition by herbicides and engineering for herbicide tolerance in crops
Pestic. Biochem. Physiol.
156
9-28
2019
Avena sativa, Arabidopsis thaliana (P93836)
Schindler, C.E.M.; Hollenbach, E.; Mietzner, T.; Schleifer, K.J.; Zacharias, M.
Free energy calculations elucidate substrate binding, gating mechanism, and tolerance-promoting mutations in herbicide target 4-hydroxyphenylpyruvate dioxygenase
Protein Sci.
28
1048-1058
2019
Zea mays, Arabidopsis thaliana (P93836), Arabidopsis thaliana
Lin, H.; Chen, X.; Chen, J.; Wang, D.; Wu, F.; Lin, S.; Zhan, C.; Wu, J.; Yang, W.; Yang, G.
Crystal structure of 4-hydroxyphenylpyruvate dioxygenase in complex with substrate reveals a new starting point for herbicide discovery
Research (Wash. D.C.)
2019
2602414
2019
Arabidopsis thaliana (P93836), Arabidopsis thaliana
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