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Information on EC 1.3.3.4 - protoporphyrinogen oxidase and Organism(s) Nicotiana tabacum and UniProt Accession O24163
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1.3.3.4 protoporphyrinogen oxidaseIUBMB Comments
This is the last common enzyme in the biosynthesis of chlorophylls and heme . Two isoenzymes exist in plants: one in plastids and the other in mitochondria. This is the target enzyme of phthalimide-type and diphenylether-type herbicides . The enzyme from oxygen-dependent species contains FAD . Also slowly oxidizes mesoporphyrinogen IX.
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Word Map
- 1.3.3.4
-
herbicide
- heme
- porphyria
- variegate
-
chlorophyl
-
weed
- coproporphyrinogen
- acifluorfen
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ferrochelatase
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diphenyl
- tetrapyrrole
- porphobilinogen
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ppo-inhibiting
- amaranthus
- flumioxazin
- tuberculatus
- glyphosate
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neurovisceral
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5-aminolevulinic
- oxyfluorfen
- acetolactate
- uroporphyrinogen
- fomesafen
- oxadiazon
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broadleaf
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target-site
- agriculture
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postemergence
- glufosinate
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waterhemp
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herbicide-resistant
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porphyrinogenic
- coproporphyria
- diphenylether
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oxidase-inhibiting
- rudis
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glyphosate-resistant
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sauer
- diagnostics
- medicine
- drug development
- mesotrione
- analysis
The taxonomic range for the selected organisms is: Nicotiana tabacum
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
protoporphyrinogen oxidase, ppox, protox, protoporphyrinogen ix oxidase, mtppo, protox enzyme, protoporphyrinogen oxidase ix, ppo1-1, ppox i, protein yfex, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PPO
PPO2
protoporphyrinogen IX oxidase
protoporphyrinogen oxidase
protoporphyrinogenase
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protox
PPO
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protoporphyrinogen IX oxidase
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protoporphyrinogen oxidase
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protox
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
protoporphyrinogen IX + 3 O2 = protoporphyrin IX + 3 H2O2
reaction mechanism and active site structure
protoporphyrinogen IX + 3 O2 = protoporphyrin IX + 3 H2O2
reaction and substrate recognition mechanisms, conformational analysis based on molecular docking, molecular dynamics (MD) simulation, molecular mechanic/Poisson-Boltzmann surface area (MM/PBSA) calculations, umbrella sampling MD simulations, and potential of mean force (PMF) calculations, overview
protoporphyrinogen IX + 3 O2 = protoporphyrin IX + 3 H2O2
reaction scheme involving FAD, overview
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
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oxidation
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
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-, -, -
SYSTEMATIC NAME
IUBMB Comments
protoporphyrinogen-IX:oxygen oxidoreductase
This is the last common enzyme in the biosynthesis of chlorophylls and heme [8]. Two isoenzymes exist in plants: one in plastids and the other in mitochondria. This is the target enzyme of phthalimide-type and diphenylether-type herbicides [8]. The enzyme from oxygen-dependent species contains FAD [9]. Also slowly oxidizes mesoporphyrinogen IX.
CAS REGISTRY NUMBER
COMMENTARY
53986-32-6
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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
protoporphyrinogen IX + 3 O2
protoporphyrin IX + 3 H2O2
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-
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?
protoporphyrinogen IX + 3 O2
protoporphyrin IX + 3 H2O2
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-
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?
protoporphyrinogen-IX + 3 O2
protoporphyrin-IX + 3 H2O2
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penultimate step of heme and chlorophyll biosynthesis
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?
protoporphyrinogen-IX + 3 O2
protoporphyrin-IX + 3 H2O2
enzyme deficiency causes variegate porphyria, bringing about e.g. light-sensitivity of human skin
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-
?
additional information
?
-
the enzyme might be complexed in vivo with the ferrochelatase for substrate channeling
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-
?
additional information
?
-
-
the enzyme might be complexed in vivo with the ferrochelatase for substrate channeling
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-
?
additional information
?
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development of a binding model for the protogen substrate protoporphyrinogen IX through extensive computational simulations, analysis of essential active site residues (protogen surrounded by R98, F172, A174, G175, T176, F353, L356, F392, and FAD in tobacco mtPPO) and mechanism of substrate recognition, docking uses the crystal structure of Nicotiana tabacum mitochondrial PPO enzyme and of the human PPO enzyme, overview
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-
?
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
protoporphyrinogen IX + 3 O2
protoporphyrin IX + 3 H2O2
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-
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?
protoporphyrinogen IX + 3 O2
protoporphyrin IX + 3 H2O2
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-
-
?
protoporphyrinogen-IX + 3 O2
protoporphyrin-IX + 3 H2O2
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penultimate step of heme and chlorophyll biosynthesis
-
?
protoporphyrinogen-IX + 3 O2
protoporphyrin-IX + 3 H2O2
enzyme deficiency causes variegate porphyria, bringing about e.g. light-sensitivity of human skin
-
-
?
additional information
?
-
the enzyme might be complexed in vivo with the ferrochelatase for substrate channeling
-
-
?
additional information
?
-
-
the enzyme might be complexed in vivo with the ferrochelatase for substrate channeling
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
binding structure analysis through molecular docking using the crystal structure of Nicotiana tabacum mitochondrial PPO enzyme, overview
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
acifluorfen
necrotic leaf lesions visible within the first hours of light exposure
(3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-5-yl)methyl acetate
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-
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(3Z)-3-[[4-chloro-2-fluoro-5-(3a,4,6,6a-tetrahydrofuro[3,4-d][1,2]oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
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-
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(3Z)-3-[[4-chloro-2-fluoro-5-(3a,5,6,6a-tetrahydrofuro[2,3-d][1,2]oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
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-
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(3Z)-3-[[4-chloro-2-fluoro-5-(5-propanoyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
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-
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(3Z)-3-[[4-chloro-5-(5-ethyl-5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-2-fluorophenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
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-
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(4-bromophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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(4-chlorophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
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(4-fluorophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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-
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(4-methylphenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
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1-(allyloxy)-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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1-(tert-butoxy)-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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1-ethoxy-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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1-ethoxy-1-oxopropan-2-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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-
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1-oxo-1-(prop-2-yn-1-yloxy)propan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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1-[2-(allylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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1-[2-(allylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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1-[2-(butylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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-
1-[2-(butylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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1-[6-chloro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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1-[6-chloro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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-
1-[6-fluoro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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-
1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
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-
2-(allyloxy)-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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-
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2-(tert-butoxy)-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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-
-
2-chloro-4-[4-[chloro(difluoro)methyl]-3-[(prop-2-yn-1-yl)oxy]phenyl]furan-3-carboxamide
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2-chloro-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl chloride
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2-chloro-N-(cyanomethyl)-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzenesulfonamide
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2-chloroethyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
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2-ethoxy-1,1-difluoro-2-oxoethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
2-ethoxy-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
2-ethoxy-2-oxoethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
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2-ethoxy-2-oxoethyl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
-
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2-fluoroethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
2-methoxy-2-oxoethyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
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2-oxo-2-(prop-2-yn-1-yloxy)ethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]acetic acid
-
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2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]propanoic acid
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-
2-[6-bromo-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-4-(difluoromethyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one
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2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]acetic acid
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2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]propanoic acid
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-(prop-2-yn-1-yl)acetamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-ethylacetamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-ethylpropanamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-methylacetamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-methylpropanamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-propylacetamide
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2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoic acid
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3-fluoropropyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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3-methylbut-2-en-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-(propan-2-yl)-4,5-dihydro-1,2-oxazole-5-carboxamide
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3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-([[methyl(propan-2-yl)amino]oxy]sulfinyl)-4,5-dihydro-1,2-oxazole-5-carboxamide
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3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-propyl-4,5-dihydro-1,2-oxazole-5-carboxamide
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-
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3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-N-ethyl-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxamide
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3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-N,5-dimethyl-4,5-dihydro-1,2-oxazole-5-carboxamide
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3-[4-chloro-2-fluoro-5-([[(5-methoxy-2-oxohexyl)sulfanyl]methyl]amino)phenyl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
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3-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-ylthio]propanoic acid
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3-[6-bromo-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-bromo-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-bromo-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-chloro-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-chloro-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-chloro-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-ylthio]propanoic acid
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-
3-[6-fluoro-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-fluoro-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
3-[6-fluoro-2-[(prop-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
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3-[6-fluoro-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
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4-bromo-3-(5'-carboxy-4'-chloro-2'-fluoro-phenyl)-1-methyl-5-trifluoromethyl-pyrazol
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5-[2-chloro-4-(trifluoromethyl)phenoxyl]-2-nitrobenzoic acid
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transgenic YZI-1S cells show a 150fold greater resistance to the inhibitor compared to wild-type cells, inhibition of mitochondrial and chloroplastic isozymes
allyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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benzyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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benzyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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butyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
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butyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
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butyl [([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
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butyl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
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butyl [([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
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butyl [([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
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-
-
cyclobutylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
cyclohexylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
cyclopentylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
cyclopropylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
ethyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)alaninate
-
-
-
ethyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
-
-
ethyl ([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
ethyl ([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
ethyl ([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]acetate
-
-
ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]propanoate
-
-
ethyl 1-[6-bromo-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
-
ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
-
ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]propanoate
-
-
ethyl 2-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)amino)methyl)thio)acetate
-
-
-
ethyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
-
ethyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
-
ethyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
-
ethyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
ethyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]propanoate
-
ethyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
-
-
-
ethyl 3-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 3-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 3-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
ethyl 3-[2-chloro-4-fluoro-5-(1-oxo-3-thioxotetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazin-2(3H)-yl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
ethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
ethyl 4-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
-
ethyl 4-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
-
ethyl 4-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
-
ethyl N-(2-bromo-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl)alaninate
-
ethyl N-(2-chloro-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl)alaninate
-
ethyl N-[2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoyl]glycinate
-
-
-
ethyl N-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetyl]glycinate
-
-
-
ethyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
ethyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
ethyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
isopropyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
methyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
-
-
methyl ([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
methyl ([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
methyl ([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
-
methyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
-
methyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
methyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
methyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
-
methyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
methyl 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluoro benzothiazol-2-ylthio]acetate
-
-
methyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
-
-
-
methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
methyl 4-[4-[chloro(difluoro)methyl]phenyl]-2-(trifluoromethyl)furan-3-carboxylate
-
methyl 5-[2-chloro-4-(trifluoromethyl)benzene-1-sulfinyl]-2-nitrobenzoate
-
methyl 5-[2-chloro-4-(trifluoromethyl)benzene-1-sulfonyl]-2-nitrobenzoate
-
methyl 5-[[2-chloro-4-(trifluoromethyl)phenyl]sulfanyl]-2-nitrobenzoate
-
methyl N-[2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoyl]-?-alaninate
-
-
-
methyl N-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetyl]-?-alaninate
-
-
-
methyl [([[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetyl)amino]acetate
-
-
-
methyl [[(E)-(1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]ethylidene)amino]oxy]acetate
-
methyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
methyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
methyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
methyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
N-butyl-3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxamide
-
-
-
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylleucinamide
-
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylnorleucinamide
-
O-ethyl S-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] carbonothioate
-
prop-2-en-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
prop-2-en-1-yl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
prop-2-yn-1-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
prop-2-yn-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
prop-2-yn-1-yl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
-
-
propan-2-yl 2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoate
-
-
-
propan-2-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
propyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
-
-
propyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
propyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
propyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
propyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
propyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
-
-
S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-ethyl carbonothioate
-
-
S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-methyl carbonothioate
-
-
S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-ethyl carbonothioate
-
-
S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-methyl carbonothioate
-
-
S-[6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-ethyl carbonothioate
-
S-[6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-ethyl carbonothioate
-
S-[6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-methyl carbonothioate
-
S-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-methyl carbonothioate
-
tert-butyl((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
-
-
[4-(trifluoromethyl)phenyl]methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
-
-
[[(E)-(1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]ethylidene)amino]oxy]acetic acid
-
[[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
-
-
[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
-
-
[[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
-
-
[[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
-
-
additional information
antisense RNA expression inhibits the formation of PPOX I in transgenic plants
-
additional information
-
antisense RNA expression inhibits the formation of PPOX I in transgenic plants
-
additional information
-
design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors, structure-activity relationships, computational simulations and binding free energy calculations, and herbicidal activities of the compounds against weeds, overview. The substituents, e.g. F, Cl, and Br, on position 2 affect the bioactive conformation of inhibitors. No inhibition by S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-methyl carbonothioate and S-6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-yl O-ethyl carbonothioate
-
additional information
-
mechanism of substrate recognition and feedback inhibition of protoporphyrinogen oxidase, overview
-
additional information
analysis of the mechanism of substrate recognition and feedback inhibition of protoporphyrinogen oxidase, overview
-
additional information
protoporphyrinogen oxidase is one of the most significant targets for a large family of inhibitors that may be used as herbicide, bactericide, fungicide, or photosensitizing activator to treat cancer through photodynamic therapy (PDT). Molecular docking and comparative molecular field analysis (CoMFA), a three-dimensional quantitative structure-activity relationship technique, are combined in a multistep framework for identifying important factor contributing to activity of PPO inhibitors, the crystal structure of tobacco mitochondrial PPO (mtPPO) is used as template, and all compounds are docked into the enzyme active site, 3D-QSAR model for PPO inhibition activity, overview
-
additional information
synthesis, herbicidal activity, and quantitative structureactivity relationship of N-benzothiazolyl-pyrimidine-2,4-diones as protoporphyrinogen oxidase inhibitors, overview
-
additional information
-
synthesis, herbicidal activity, and quantitative structureactivity relationship of N-benzothiazolyl-pyrimidine-2,4-diones as protoporphyrinogen oxidase inhibitors, overview
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
Michaelis-Menten kinetics
-
0.00117
protoporphyrinogen IX
-
pH 7.4, temperature not specified in the publication, wild-type enzyme
0.0083
protoporphyrinogen IX
-
pH 7.4, temperature not specified in the publication, mutant R98A
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6
protoporphyrinogen IX
-
pH 7.4, temperature not specified in the publication, wild-type enzyme
365
protoporphyrinogen IX
-
pH 7.4, temperature not specified in the publication, mutant R98A
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0000048
(3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazol-5-yl)methyl acetate
-
at pH 7.4, temperature not specified in the publication
-
0.00001
(3Z)-3-[[4-chloro-2-fluoro-5-(3a,4,6,6a-tetrahydrofuro[3,4-d][1,2]oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
-
at pH 7.4, temperature not specified in the publication
-
0.000018
(3Z)-3-[[4-chloro-2-fluoro-5-(3a,5,6,6a-tetrahydrofuro[2,3-d][1,2]oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
-
at pH 7.4, temperature not specified in the publication
-
0.000038
(3Z)-3-[[4-chloro-2-fluoro-5-(5-propanoyl-4,5-dihydro-1,2-oxazol-3-yl)phenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one, (3Z)-3-[[4-chloro-5-(5-ethyl-5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-2-fluorophenyl]imino]tetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one
-
at pH 7.4, temperature not specified in the publication
-
0.000023
(4-bromophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate, (4-chlorophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000048
(4-fluorophenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000024
(4-methylphenyl)methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000011
1-(allyloxy)-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000004
1-(tert-butoxy)-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000006
1-ethoxy-1-oxopropan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.00003
1-ethoxy-1-oxopropan-2-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000012
1-oxo-1-(prop-2-yn-1-yloxy)propan-2-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.01278
1-[2-(allylthio)-6-bromobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00313
1-[2-(allylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.0002
1-[2-(allylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00297
1-[2-(butylthio)-6-chlorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00021
1-[2-(butylthio)-6-fluorobenzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.01386
1-[6-chloro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00201
1-[6-chloro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00051
1-[6-fluoro-2-(methylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.0003
1-[6-fluoro-2-(propylthio)benzothiazol-5-yl]-3-methyl-4-difluoromethyl-1H-1,2,4-triazol-5(4H)-one
-
pH 7.5, 22°C, recombinant enzyme
0.00001
2-(allyloxy)-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000005
2-(tert-butoxy)-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000013
2-chloro-N-(cyanomethyl)-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzenesulfonamide
-
pH and temperature not specified in the publication
-
0.0000012
2-chloroethyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
-
pH and temperature not specified in the publication
-
0.000044
2-ethoxy-1,1-difluoro-2-oxoethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000019
2-ethoxy-2-oxoethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000015
2-ethoxy-2-oxoethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000044
2-ethoxy-2-oxoethyl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000022
2-fluoroethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000157
2-methoxy-2-oxoethyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000014
2-oxo-2-(prop-2-yn-1-yloxy)ethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.00152
2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]acetic acid
-
pH 7.5, 22°C, recombinant enzyme
0.00121
2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluorobenzothiazol-2-ylthio]propanoic acid
-
pH 7.5, 22°C, recombinant enzyme
0.01026
2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]acetic acid
-
pH 7.5, 22°C, recombinant enzyme
0.00673
2-[6-chloro-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)benzothiazol-2-ylthio]propanoic acid
-
pH 7.5, 22°C, recombinant enzyme
0.0000668
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-(prop-2-yn-1-yl)acetamide
-
pH and temperature not specified in the publication
-
0.0000036
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-ethylacetamide
-
pH and temperature not specified in the publication
-
0.0000026
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-ethylpropanamide
-
pH and temperature not specified in the publication
-
0.0000271
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-methylacetamide
-
pH and temperature not specified in the publication
-
0.0000167
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-methylpropanamide
-
pH and temperature not specified in the publication
-
0.000003
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]-N-propylacetamide
-
pH and temperature not specified in the publication
-
0.0000145
2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoic acid
-
pH and temperature not specified in the publication
-
0.000087
3-fluoropropyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.00003
3-methylbut-2-en-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.00007
3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-(propan-2-yl)-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.000022
3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-([[methyl(propan-2-yl)amino]oxy]sulfinyl)-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.000088
3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-N-propyl-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.000024
3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-N-ethyl-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.00006
3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-N,5-dimethyl-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.0000086
3-[4-chloro-2-fluoro-5-([[(5-methoxy-2-oxohexyl)sulfanyl]methyl]amino)phenyl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
-
pH and temperature not specified in the publication
-
0.00167
3-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-ylthio]propanoic acid
-
pH 7.5, 22°C, recombinant enzyme
0.06632
3-[6-bromo-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.01129
3-[6-bromo-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.1301
3-[6-bromo-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.00109
3-[6-chloro-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.00046
3-[6-chloro-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.00488
3-[6-chloro-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.01779
3-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]benzothiazol-2-ylthio]propanoic acid
-
pH 7.5, 22°C, recombinant enzyme
0.000012
3-[6-fluoro-2-[(2-oxopentyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.000011
3-[6-fluoro-2-[(3-methyl-2-oxobutyl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.000014
3-[6-fluoro-2-[(prop-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.000019
3-[6-fluoro-2-[(prop-2-yn-1-yl)sulfanyl]-1,3-benzothiazol-5-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
pH 7.5, 22°C
0.00002
allyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000015
benzyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000027
benzyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000007
butyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.0000137
butyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000189
butyl [([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000155
butyl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000412
butyl [([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000234
butyl [([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000027
cyclobutylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000017
cyclohexylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000016
cyclopentylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000028
cyclopropylmethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000005
ethyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)alaninate
-
pH and temperature not specified in the publication
-
0.000006
ethyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
pH and temperature not specified in the publication
-
0.00484
ethyl ([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.00045
ethyl ([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.000009
ethyl ([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.00006
ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]acetate
-
pH 7.5, 22°C, recombinant enzyme
0.00024
ethyl 1-[5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluoro benzothiazol-2-ylthio]propanoate
-
pH 7.5, 22°C, recombinant enzyme
0.008
ethyl 1-[6-bromo-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
pH 7.5, 22°C, recombinant enzyme
0.00137
ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
pH 7.5, 22°C, recombinant enzyme
0.00339
ethyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]propanoate
-
pH 7.5, 22°C, recombinant enzyme
0.000011
ethyl 2-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenyl)amino)methyl)thio)acetate
-
pH and temperature not specified in the publication
-
0.00169
ethyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
pH 7.5, 22°C
0.00225
ethyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.00532
ethyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
pH 7.5, 22°C
0.00139
ethyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.0000072
ethyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate
pH 7.5, 22°C
0.000014
ethyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.000009
ethyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.0000023
ethyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
-
pH and temperature not specified in the publication
-
0.00217
ethyl 3-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.00012
ethyl 3-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.0000073
ethyl 3-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.0000046
ethyl 3-[2-chloro-4-fluoro-5-(1-oxo-3-thioxotetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazin-2(3H)-yl)phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000218
ethyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.00294
ethyl 4-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
pH 7.5, 22°C
0.00021
ethyl 4-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
pH 7.5, 22°C
0.000013
ethyl 4-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)butanoate
pH 7.5, 22°C
0.0000085
ethyl N-[2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoyl]glycinate
-
pH and temperature not specified in the publication
-
0.0000153
ethyl N-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetyl]glycinate
-
pH and temperature not specified in the publication
-
0.0000107
ethyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000063
ethyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000135
ethyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000015
fluthiacet-methyl
-
at pH 7.4, temperature not specified in the publication
-
0.000012
isopropyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.00001
methyl ((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
pH and temperature not specified in the publication
-
0.09854
methyl ([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.00485
methyl ([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.000032
methyl ([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)acetate
pH 7.5, 22°C
0.01518
methyl 1-[6-chloro-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl] benzothiazol-2-ylthio]acetate
-
pH 7.5, 22°C, recombinant enzyme
0.01723
methyl 2-([6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.00864
methyl 2-([6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.000016
methyl 2-([6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl]sulfanyl)propanoate
pH 7.5, 22°C
0.000015
methyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.00108
methyl 2-[5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-6-fluoro benzothiazol-2-ylthio]acetate
-
pH 7.5, 22°C, recombinant enzyme
0.0000226
methyl 2-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]propanoate
-
pH and temperature not specified in the publication
-
0.000033
methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.00002
methyl N-[2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoyl]-?-alaninate
-
pH and temperature not specified in the publication
-
0.000067
methyl N-[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetyl]-?-alaninate
-
pH and temperature not specified in the publication
-
0.0000478
methyl [([[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetyl)amino]acetate
-
pH and temperature not specified in the publication
-
0.0000064
methyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000286
methyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000051
methyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000103
methyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000048
N-butyl-3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxamide
-
at pH 7.4, temperature not specified in the publication
-
0.000065
O-ethyl S-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] carbonothioate
pH 7.5, 22°C
0.000021
prop-2-en-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000378
prop-2-en-1-yl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.000014
prop-2-yn-1-yl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000033
prop-2-yn-1-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000262
prop-2-yn-1-yl [([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000056
propan-2-yl 2-[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]anilino]methyl)sulfanyl]propanoate
-
pH and temperature not specified in the publication
-
0.0000076
propan-2-yl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.000008
propyl 2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)benzoate
-
pH and temperature not specified in the publication
-
0.000015
propyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000117
propyl [[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000174
propyl [[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate, propyl [[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.0000224
propyl [[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetate
-
pH and temperature not specified in the publication
-
0.00058
S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-ethyl carbonothioate
-
pH 7.5, 22°C, recombinant enzyme
0.00029
S-5-[4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl]-6-fluorobenzothiazol-2-yl O-methyl carbonothioate
-
pH 7.5, 22°C, recombinant enzyme
0.08112
S-[6-bromo-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-ethyl carbonothioate
pH 7.5, 22°C
0.00704
S-[6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-ethyl carbonothioate
pH 7.5, 22°C
0.00476
S-[6-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-methyl carbonothioate
pH 7.5, 22°C
0.000036
S-[6-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]-1,3-benzothiazol-2-yl] O-methyl carbonothioate
pH 7.5, 22°C
0.000014
tert-butyl((2-chloro-4-fluoro-5-(4-oxo-5,6,7,8-tetrahydroquinazolin-3(4H)-yl)phenyl)sulfonyl)glycinate
-
pH and temperature not specified in the publication
-
0.000058
[4-(trifluoromethyl)phenyl]methyl 3-[2-chloro-4-fluoro-5-[(Z)-(3-oxotetrahydro-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
-
at pH 7.4, temperature not specified in the publication
-
0.0000381
[[([2,4-dichloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
pH and temperature not specified in the publication
-
0.000011
[[([2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
pH and temperature not specified in the publication
-
0.0000469
[[([2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
pH and temperature not specified in the publication
-
0.0000269
[[([4-bromo-2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl]amino)methyl]sulfanyl]acetic acid
-
pH and temperature not specified in the publication
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.03963
1-nitro-4-phenoxybenzene
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000022
2-chloro-4-[4-[chloro(difluoro)methyl]-3-[(prop-2-yn-1-yl)oxy]phenyl]furan-3-carboxamide
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.00558
2-chloro-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl chloride
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000061
2-chloro-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carboxamide
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000014
2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]furan
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.02616
5-[2-chloro-5-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000032
benzofluorfen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000057 - 0.02279
ethyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]propanoate
0.000199
ethyl N-(2-bromo-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl)alaninate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000357
ethyl N-(2-chloro-4-[4-[chloro(difluoro)methyl]phenyl]furan-3-carbonyl)alaninate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000147
fluorodifen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000031
fomesafen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000062
lactofen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000053
methyl 2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000599
methyl 4-[4-[chloro(difluoro)methyl]phenyl]-2-(trifluoromethyl)furan-3-carboxylate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.01254
methyl 5-[2-chloro-4-(trifluoromethyl)benzene-1-sulfinyl]-2-nitrobenzoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.0474
methyl 5-[2-chloro-4-(trifluoromethyl)benzene-1-sulfonyl]-2-nitrobenzoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.00222
methyl 5-[2-chloro-5-(trifluoromethyl)phenoxy]-2-nitrobenzoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000048
methyl 5-[[2-chloro-4-(trifluoromethyl)phenyl]sulfanyl]-2-nitrobenzoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000014
methyl [[(E)-(1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]ethylidene)amino]oxy]acetate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000015 - 0.000027
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylleucinamide
0.000012 - 0.000027
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylnorleucinamide
0.000406
nitrofen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.00007
nitrofluorfen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000054
oxyfluorfen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.00001
[[(E)-(1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]ethylidene)amino]oxy]acetic acid
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000019
acifluorfen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.00007
acifluorfen
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000057
ethyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]propanoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.02279
ethyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]propanoate
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000015
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylleucinamide
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000027
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylleucinamide
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
0.000012
N2-(5-[[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]oxy]-2-nitrophenyl)-N-methylnorleucinamide
Nicotiana tabacum
pH 7.4, temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
activity in chloroplast of wild-type and transgenic cells is similar for both isozymes, while the transgenic mitochondria show 5.3fold higher activity than those from the wild-type
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
7.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
22
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
transgenic cell with 150fold greater resistance to inhibitor S23142
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
activity in chloroplast of wild-type and transgenic cells is similar for both isozymes, while the transgenic mitochondria show 5.3fold higher activity than those from the wild-type
-
isozyme PPO2, outer surface of the inner membrane
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
metabolism
physiological function
protoporphyrinogen IX oxidase catalyzes the oxidation of protoporphyrinogen IX (protogen IX) to protoporphyrin IX (proto IX) in the haem/chlorophyll biosynthetic pathway
additional information
malfunction
-
inhibition or functional loss of PPO results in the accumulation of protogen, which can be spontaneously oxidized to proto by oxygen. As a photosensitizer, in the presence of light, proto can further induce the production of singlet oxygen, causing lipid peroxidation and cell death
malfunction
deficient activity of PPO causes the accumulation and nonenzymatic oxidation of protogen IX leading to cellular damage. For green plants, inhibition of PPO leads to the rapid bleaching and desiccation of photosynthetically active parts of the plant
metabolism
-
protoporphyrinogen IX oxidase is an essential enzyme catalyzing the last common step in the pathway leading to heme and chlorophyll biosynthesis
metabolism
protoporphyrinogen IX oxidase is an essential enzyme catalyzing the last common step in the pathway leading to heme and chlorophyll biosynthesis
metabolism
protoporphyrinogen oxidase (PPO) is a key enzyme in the tetrapyrrole biosynthesis
additional information
-
substrate binding model, molecular docking studies, overview. The protogen is surrounded by R98, F172, A174, G175, T176, F353, L356, F392, and FAD in tobacco mtPPO. Possible role of R98 during the substrate recognition mechanism,
additional information
analysis of binding mode of protogen IX in the Nicotiana tabacum protoporphyrinogen IX oxidase (mtPPO) by performing a computational docking followed by molecular simulations, quantum mechanics calculations, and an integrated analysis, overview. Several potential key residues, e.g. Thr70, Arg233, Ser235, Ser474 and Lys477, are identified. Residue Arg98 is necessary for binding of protogen IX. Comparison of the Nicotiana tabacum enzyme with the human enzyme. Modeling of ligand binding structures
additional information
-
analysis of binding mode of protogen IX in the Nicotiana tabacum protoporphyrinogen IX oxidase (mtPPO) by performing a computational docking followed by molecular simulations, quantum mechanics calculations, and an integrated analysis, overview. Several potential key residues, e.g. Thr70, Arg233, Ser235, Ser474 and Lys477, are identified. Residue Arg98 is necessary for binding of protogen IX. Comparison of the Nicotiana tabacum enzyme with the human enzyme. Modeling of ligand binding structures
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). PPOC_TOBAC
548
0
59230
Swiss-Prot
Chloroplast (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
dimer interface structure, domain structure, overview
additional information
-
dimer interface structure, domain structure, overview
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified selenomethionine-labeled, recombinant mitochondrial isozyme PPO2 free or in complex with inhibitor 4-bromo-3-(5'-carboxy-4'-chloro-2'-fluoro-phenyl)-1-methyl-5-trifluoromethyl-pyrazol and with FAD, protein solution contains protein, 5 mM Tris-HCl, pH 8.0, 0.1% Triton X-100, 50 mM sodium chloride, hanging drop vapour diffusion method, 18°C, precipitant solution contains 10% PEG 1000, 0.1 M sodium citrate-HCl, pH 4.0, and 0.2 M sodium chloride, 2 days, selenium single anomalous X-ray diffraction structure determination and analysis at 2.9 A resolution, molecular modelling
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F392E
F392H
L356N
L356V
L372N
L372V
N67R
N67R/S374D
N67W/S374D
R98A
R98E
R98K
S374D
additional information
F392E
-
inferior binding of the substrate, but increased turnover rate than wild-type
F392E
site-directed mutagenesis, calculation of free binding energy shifts
F392H
-
does not reveal detectable enzyme activity indicating an important role of Phe392 in substrate ring A stacking
L356N
-
an only slightly inferior binding capacity compared with the wild-type and comparable catalytic PPO2 activities
L356N
site-directed mutagenesis, calculation of free binding energy shifts
L356V
-
increased Km value, once the substrate is bound, catalysis is enhanced
L356V
site-directed mutagenesis, calculation of free binding energy shifts
L372N
-
an only slightly inferior binding capacity compared with the wild-type and comparable catalytic PPO2 activities
L372N
site-directed mutagenesis, calculation of free binding energy shifts
L372V
-
increased Km value, once the substrate is bound, catalysis is enhanced
L372V
site-directed mutagenesis, calculation of free binding energy shifts
N67W/S374D
-
shows increased activity, structural constellation mimicking the human disease variegate porphyria
R98A
-
site-directed mutagenesis, the mutant has a 60fold increased catalytic activity compared to the wild-type enzyme
R98A
site-directed mutagenesis, calculation of free binding energy shifts
R98E
site-directed mutagenesis, calculation of free binding energy shifts
R98K
site-directed mutagenesis, calculation of free binding energy shifts
additional information
transgenic lines, expression levels of PPOX I mRNA and protein and the cellular enzyme activities are reduced to similar extents in transgenic plants grown under low- or high-light conditions, more necrotic leaf lesions are surprisingly generated under low- than under high-light exposure
additional information
-
transgenic lines, expression levels of PPOX I mRNA and protein and the cellular enzyme activities are reduced to similar extents in transgenic plants grown under low- or high-light conditions, more necrotic leaf lesions are surprisingly generated under low- than under high-light exposure
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
both isozymes partially from cell culture of wild-type and transgenic cells, by chloroplast and mitochondria fractionation, detergent solubilization, and ultracentrifugation
-
recombinant thioredoxin- and His-tagged, selenomethionine-labeled enzyme from Escherichia coli by nickel affinity chromatography, 3-step purification process
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli BL21(DE3)RIL containing the original or mutated pET32a-PPO2 plasmids
-
expression of the thioredoxin- and His-tagged enzyme in Escherichia coli strain B834(DE3), selenomethionine labeling in the auxothrophic strain
gene PPX2, recombinant expression in Escherichia coli strain BL21(DE3)-pLysS
overproduction of mitochondrial isozyme by gene amplification in photomixotrophic cells
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
drug development
enzyme PPO is an excellent target for commercial herbicides
medicine
-
tobacco PPO2 represents a useful model system for the understanding of the structurefunction relationship underlying detrimental human enzyme defects, Arg98, Phe392, Leu356 and Leu372 are functionally involved in substrate co-ordination within the active site
additional information
agriculture
enzyme is a target for light-dependent peroxidizing herbicides
agriculture
-
protoporphyrinogen oxidase is the action target for several structurally diverse herbicides
additional information
light intensity-dependent degradation of reduced and oxidized porphyrins prevents severe photodynamic leaf damage, moreover, under high-light conditions, elevated contents of reduced and total low-molecular-weight antioxidants, which contribute to the protection against photosensitizing porphyrins
additional information
-
light intensity-dependent degradation of reduced and oxidized porphyrins prevents severe photodynamic leaf damage, moreover, under high-light conditions, elevated contents of reduced and total low-molecular-weight antioxidants, which contribute to the protection against photosensitizing porphyrins
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lermontova, I.; Kruse, E.; Mock, H.P.; Grimm, B.
Cloning and characterization of a plastidal and a mitochondrial isoform of tobacco protoporphyrinogen IX oxidase
Proc. Natl. Acad. Sci. USA
94
8895-8900
1997
Nicotiana tabacum
Watanabe, N.; Takayama, S.; Yoshida, S.; Isogai, A.; Che, F.S.
Resistance to protoporphyrinogen oxidase-inhibiting compound S23142 from overproduction of mitochondrial protoporphyrinogen oxidase by gene amplification in photomixotrophic tobacco cells
Biosci. Biotechnol. Biochem.
66
1799-1805
2002
Nicotiana tabacum
Koch, M.; Breithaupt, C.; Kiefersauer, R.; Freigang, J.; Huber, R.; Messerschmidt, A.
Crystal structure of protoporphyrinogen IX oxidase: a key enzyme in haem and chlorophyll biosynthesis
EMBO J.
23
1720-1728
2004
Nicotiana tabacum (O24164), Nicotiana tabacum
Heinemann, I.U.; Diekmann, N.; Masoumi, A.; Koch, M.; Messerschmidt, A.; Jahn, M.; Jahn, D.
Functional definition of the tobacco protoporphyrinogen IX oxidase substrate binding site
Biochem. J.
402
575-580
2007
Nicotiana tabacum
Lermontova, I.; Grimm, B.
Reduced activity of plastid protoporphyrinogen oxidase causes attenuated photodynamic damage during high-light compared to low-light exposure
Plant J.
48
499-510
2006
Nicotiana tabacum (O24163), Nicotiana tabacum
Yang, Z.; Sheng-Gang, Y.; Yan-Ping, L.; Ying, T.; Ge-Fei, H.; Qiong-You, W.; Zhen, X.; Guang-Fu, Y.
Design and synthesis of 1-(benzothiazol-5-yl)-1H-1,2,4-triazol-5-ones as protoporphyrinogen oxidase inhibitors
Bioorg. Med. Chem.
21
3245-3255
2013
Nicotiana tabacum
Hao, G.F.; Tan, Y.; Yang, S.G.; Wang, Z.F.; Zhan, C.G.; Xi, Z.; Yang, G.F.
Computational and experimental insights into the mechanism of substrate recognition and feedback inhibition of protoporphyrinogen oxidase
PLoS ONE
8
e69198
2013
Homo sapiens, Nicotiana tabacum
Yang, S.; Hao, G.; Dayan, F.; Tranel, P.; Yang, G.
Insight into the structural requirements of protoporphyrinogen oxidase inhibitors molecular docking and CoMFA of diphenyl ether, isoxazole phenyl, and pyrazole phenyl ether
Chin. J. Chem.
31
1153-1158
2013
Nicotiana tabacum (O24164)
-
Zuo, Y.; Wu, Q.; Su, S.W.; Niu, C.W.; Xi, Z.; Yang, G.F.
Synthesis, herbicidal activity, and QSAR of novel N-benzothiazolyl-pyrimidine-2,4-diones as protoporphyrinogen oxidase inhibitors
J. Agric. Food Chem.
64
552-562
2016
Nicotiana tabacum (O24164), Nicotiana tabacum
Wang, B.; Wen, X.; Xi, Z.
Molecular simulations bring new insights into protoporphyrinogen IX oxidase/protoporphyrinogen IX interaction modes
Mol. Inform.
35
476-482
2016
Nicotiana tabacum (O24164), Nicotiana tabacum
Hao, G.F.; Tan, Y.; Yang, S.G.; Wang, Z.F.; Zhan, C.G.; Xi, Z.; Yang, G.F.
Computational and experimental insights into the mechanism of substrate recognition and feedback inhibition of protoporphyrinogen oxidase
PLoS ONE
8
e69198
2013
Nicotiana tabacum (O24164), Homo sapiens (P50336)
Liang, L.; Yu, S.; Li, Q.; Wang, X.; Wang, D.; Xi, Z.
Design, synthesis, and molecular simulation studies of N-phenyltetrahydroquinazolinones as protoporphyrinogen IX oxidase inhibitors
Bioorg. Med. Chem.
39
116165
2021
Nicotiana tabacum
Zhang, R.B.; Yu, S.Y.; Liang, L.; Ismail, I.; Wang, D.W.; Li, Y.H.; Xu, H.; Wen, X.; Xi, Z.
Design, synthesis, and molecular mechanism studies of N-phenylisoxazoline-thiadiazolo[3,4-a]pyridazine hybrids as protoporphyrinogen IX oxidase inhibitors
J. Agric. Food Chem.
68
13672-13684
2020
Nicotiana tabacum
Wang, D.W.; Liang, L.; Xue, Z.Y.; Yu, S.Y.; Zhang, R.B.; Wang, X.; Xu, H.; Wen, X.; Xi, Z.
Discovery of N-phenylaminomethylthioacetylpyrimidine-2,4-diones as protoporphyrinogen IX oxidase inhibitors through a reaction intermediate derivation approach
J. Agric. Food Chem.
69
4081-4092
2021
Nicotiana tabacum
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