Information on EC 1.3.3.4 - protoporphyrinogen oxidase and Organism(s) Homo sapiens and UniProt Accession P50336

-

PPO

-

PPOX

protoporphyrinogen IX oxidase

-

PPO

PPOX

-

654874, 655194, 672962, 697206

protoporphyrinogen IX oxidase

protoporphyrinogen oxidase

protoporphyrinogenase

-

protox

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

residues G40, L85, G232, H281, V282, L295, V335, S350, L444, G453, L15, R38, L73, V84, D143, R152, L154, V158, R168, A172, V290, and G453 are essential for enzyme activity

-

Biosynthesis of secondary metabolites, Porphyrin and chlorophyll metabolism

redox reaction

-

oxidation

-

reduction

-

BRENDA

heme metabolism

KEGG

-

-, -, -

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.

53986-32-6

-

protoporphyrinogen IX + 3 O2

protoporphyrin IX + 3 H2O2

-

-

?

protoporphyrinogen-IX + 3 O2

protoporphyrin-IX + 3 H2O2

mesoporphyrinogen-IX + 3 O2

mesoporphyrin-IX + 3 H2O2

protoporphyrinogen IX + 3 O2

protoporphyrin IX + 3 H2O2

-

724554, 725177, 726346, 764083, 764914, 765697

-

?

protoporphyrinogen-IX + 3 O2

protoporphyrin-IX + 3 H2O2

15 entries

additional information

?

-

protoporphyrinogen IX + 3 O2

protoporphyrin IX + 3 H2O2

-

-

?

protoporphyrinogen-IX + 3 O2

protoporphyrin-IX + 3 H2O2

the penultimate step in the heme biosynthesis, enzyme deficiency causes variegate porphyria

-

?

protoporphyrinogen IX + 3 O2

protoporphyrin IX + 3 H2O2

-

724554, 725177, 726346, 764083, 764914, 765697

-

?

protoporphyrinogen-IX + 3 O2

protoporphyrin-IX + 3 H2O2

8 entries

additional information

?

-

-

mutations of enzyme-encoding gene PPOX are involved in variegate porphyria, an acute hepatic porphyria, which is characterized by skin lesions and acute neuropsychatric/cisceral attacks due to enzyme deficiency

655700

-

?

FAD

FAD

acifluorfen

-

chlorphthalim

-

fomesafen

-

oxadiazon

-

sulfentrazone

-

(2,4-dichlorophenyl)hydrazine

-

(2-bromo-4-fluorophenyl)hydrazine

-

(4-chloro-2-fluorophenyl)hydrazine

-

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)urea

-

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-(4-chlorophenyl)urea

-

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-methylurea

-

2,4-dichloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

2,6-dichloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

2-(2,4-dichloro-5-propoxyphenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(3-amino-4-chlorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-bromo-2-fluoro-5-hydroxyphenyl)-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-bromo-2-fluoro-5-hydroxyphenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-2-ethoxy-5-nitrophenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-hydroxyoctahydro-1H-isoindol-1-one

-

2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-methoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-2-fluoro-5-methoxyphenyl)hexahydro-1H-isoindole-1,3(2H)-dione

-

2-(4-chloro-2-fluoro-5-propoxy-phenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one

-

2-(4-chloro-2-fluoro-5-[(3-fluorobenzyl)oxy]phenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-5-ethoxy-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-ethoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-methoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-(5-allyloxy-4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one

-

2-(6-(1,3-dioxoisoindolin-2-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetonitrile

-

2-(7-fluoro-2-methyl-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylisoindoline-1,3-dione

-

2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylisoindoline-1,3-dione

-

2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-dione

-

2-chloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)-6-fluorobenzamide

-

2-[2,4-dichloro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

2-[4-chloro-2-fluoro-5-(propan-2-yloxy)phenyl]-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

2-[4-chloro-5-(cyclopentyloxy)-2-fluorophenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

3-(2-bromo-4-fluoro-5-nitrophenyl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-(2-bromo-4-fluorophenyl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-1,1-diisopropylurea

-

3-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)phenyl)-1,1-diisopropylurea

-

3-(5-amino-2,4-dichlorophenyl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-(5-amino-2-bromo-4-fluorophenyl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-(5-amino-4-chloro-2-fluorophenyl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-(6-bromo-2-[(3-methylbut-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

3-chloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-2,2-dimethylpropanamide

-

3-[6-bromo-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

712221, 724554

3-[6-bromo-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-5-tert-butyl-1,3,4-thiadiazol-2(3H)-one

-

4-chloro-phthalimide

-

4-fluoro-2-(7-fluoro-2-methyl-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-dione

-

5-tert-butyl-3-(2,4-dichloro-5-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-(2-[(3,3-dichloroprop-2-en-1-yl)sulfanyl]-6-fluoro-1,3-benzothiazol-5-yl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-(4-chloro-2-fluoro-5-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-(4-chloro-2-fluorophenyl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-(6-chloro-2-[(3,3-dichloroprop-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl)-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-[6-chloro-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-[6-chloro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

712221, 724554

5-tert-butyl-3-[6-chloro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-thiadiazol-2(3H)-one

-

5-tert-butyl-3-[6-fluoro-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-[6-fluoro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

5-tert-butyl-3-[6-fluoro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-thiadiazol-2(3H)-one

-

acifluorfen

Atrazine

-

bilirubin

-

inhibition potency with recombinant wild-type and mutant enzymes, overview

biliverdin IX hydrochloride

-

inhibition potency with recombinant wild-type and mutant enzymes, overview

butafenacil

-

chlornitrofen

-

chlortoluron

-

-

cobalt-protoporphyrin

-

diphenylene iodonium

-

50% inhibition at 0.1 mM

391012

ethyl (2,4-dichloro-5-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]phenoxy)acetate

-

-

ethyl (2,4-dichloro-5-[[(Z)-[4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate

-

-

ethyl (2,4-dichloro-5-[[(Z)-[6-fluoro-4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate

-

-

ethyl (2,4-dichloro-5-[[(Z)-[6-nitro-4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate

-

-

ethyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

ethyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

ethyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

ethyl 2-((5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)sulfanyl)propanoate

-

with a broad spectrum of postemergence herbicidal activity

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-phenylacetate

-

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate

-

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate

-

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

ethyl 2-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate

-

ethyl 2-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate

-

ethyl 2-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

ethyl 2-[2-chloro-4-fluoro-5-(1-hydroxy-3-oxooctahydro-2H-isoindol-2-yl)phenoxy]propanoate

-

ethyl 2-[2-chloro-5-(1,3-dioxooctahydro-2H-isoindol-2-yl)-4-fluorophenoxy]propanoate

-

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

ethyl 3-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

ethyl 4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

ethyl 4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

ethyl 4-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

ethyl [2,4-dichloro-5-[(E)-(2,5-dihydroxybenzylidene)amino]phenoxy]acetate

-

-

ethyl [2,4-dichloro-5-[(E)-(2-hydroxy-3-methoxybenzylidene)amino]phenoxy]acetate

-

-

ethyl [2,4-dichloro-5-[(E)-(2-hydroxy-4-methylbenzylidene)amino]phenoxy]acetate

-

-

ethyl [2,4-dichloro-5-[(E)-(5-chloro-2-hydroxybenzylidene)amino]phenoxy]acetate

-

-

ethyl [2-chloro-4-fluoro-5-(1-hydroxy-3-oxooctahydro-2H-isoindol-2-yl)phenoxy]acetate

-

ethyl [2-chloro-5-(1,3-dioxooctahydro-2H-isoindol-2-yl)-4-fluorophenoxy]acetate

-

ethyl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

ethyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

formesafen

-

-

heme

-

0.001 mM cause 25% inhibition

lactofen

-

metalloporphyrin

-

Mn- and Co-protoporphyrin, weak inhibition by Cd-, Ni- and Fe-protoporphyrin, 5 min preincubation

-

methyl (2E)-4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)but-2-enoate

-

methyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

methyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

methyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

methyl 2-((5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)thio)acetate

-

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate

-

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate

-

methyl 3-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-sulfanylidene-1,3,5-triazinan-1-yl)-4-fluorophenyl]-5-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

-

i.e. BaR-2

-

methyl acifluorfen

-

inhibition potency with recombinant wild-type and mutant enzymes, overview

methyl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

methyl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

methyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

methyl [[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

N'-(2,4-dichlorophenyl)-2,2-dimethylpropanehydrazide

-

N'-(2-bromo-4-fluorophenyl)-2,2-dimethylpropanehydrazide

-

N'-(4-chloro-2-fluorophenyl)-2,2-dimethylpropanehydrazide

-

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)-3-(trifluoromethoxy)benzamide

-

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)phenylcarbamoyl)benzamide

-

oxadiargyl

oxadiazon

oxyfluorfen

-

pentoxazone

-

derived from chlorphthalim

phenyl 2-[[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 3-[[6-chloro-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl 4-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

phenyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

phenyl [[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propan-2-yl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propan-2-yl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propan-2-yl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propan-2-yl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propan-2-yl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propan-2-yl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propan-2-yl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

propyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propyl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propyl [[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

propyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

S-(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl) O-methyl carbonothioate

-

S-[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

712221, 724554

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-methyl carbonothioate

-

S-[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

S-[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

S-[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl] O-methyl carbonothioate

-

S-[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

saflufenacil

-

sulfentrazone

tert-butyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

tert-butyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

tert-butyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

additional information

-

0.00208 - 0.01965

protoporphyrinogen IX

0.0005

Mesoporphyrinogen-IX

-

biphasic curve, second Km: 0.004

0.001162 - 0.0196

protoporphyrinogen IX

19 entries

0.00016 - 0.0038

protoporphyrinogen-IX

13 entries

additional information

-

0.0062 - 1.273

protoporphyrinogen IX

0.0062 - 1.273

protoporphyrinogen IX

19 entries

0.00333 - 5.95

protoporphyrinogen-IX

2.81 - 136.4

protoporphyrinogen IX

19 entries

0.000025

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-(3-(trifluoromethyl)phenyl)urea

-

0.000028

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-(4-chlorophenyl)urea

-

0.00037

1-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-3-methylurea

-

0.000027

2,4-dichloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

0.000013

2,6-dichloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

0.0003

2-(2,4-dichloro-5-propoxyphenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.02764

2-(3-amino-4-chlorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.04135

2-(4-bromo-2-fluoro-5-hydroxyphenyl)-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.01935

2-(4-bromo-2-fluoro-5-hydroxyphenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.3586

2-(4-chloro-2-ethoxy-5-nitrophenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.131

2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-hydroxyoctahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

17.99

2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-methoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

44.77

2-(4-chloro-2-fluoro-5-methoxyphenyl)hexahydro-1H-isoindole-1,3(2H)-dione

-

pH not specified in the publication, temperature not specified in the publication

0.000095

2-(4-chloro-2-fluoro-5-propoxy-phenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.00078

2-(4-chloro-2-fluoro-5-[(3-fluorobenzyl)oxy]phenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.0002

2-(4-chloro-5-ethoxy-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.06658

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.00702

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-ethoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

40.6

2-(4-chloro-5-[(3-chlorobenzyl)oxy]-2-fluorophenyl)-3-methoxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.00012

2-(5-allyloxy-4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.001

2-(6-(1,3-dioxoisoindolin-2-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetonitrile

-

0.0048

2-(7-fluoro-2-methyl-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylisoindoline-1,3-dione

-

0.0028

2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-methylisoindoline-1,3-dione

-

0.0033

2-(7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-dione

-

0.0000083

2-chloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)-6-fluorobenzamide

-

16.62

2-[2,4-dichloro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.03313

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-(prop-2-en-1-yloxy)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

40.6

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.04483

2-[4-chloro-2-fluoro-5-(prop-2-en-1-yloxy)phenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.06363

2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.00069

2-[4-chloro-2-fluoro-5-(propan-2-yloxy)phenyl]-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.02464

2-[4-chloro-5-(cyclopentyloxy)-2-fluorophenyl]-3-hydroxyoctahydro-1H-isoindol-1-one

-

pH not specified in the publication, temperature not specified in the publication

0.00023

3-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-1,1-diisopropylurea

-

0.00029

3-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)phenyl)-1,1-diisopropylurea

-

0.01863

3-(6-bromo-2-[(3-methylbut-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl)-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.00087

3-chloro-N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenyl)-2,2-dimethylpropanamide

-

0.01112

3-[6-bromo-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-5-tert-butyl-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.0207

3-[6-bromo-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-5-tert-butyl-1,3,4-thiadiazol-2(3H)-one

-

pH and temperature not specified in the publication

0.0879

4-chloro-phthalimide

-

pH not specified in the publication, temperature not specified in the publication

0.005

4-fluoro-2-(7-fluoro-2-methyl-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)isoindoline-1,3-dione

-

0.01092

5-tert-butyl-3-(2-[(3,3-dichloroprop-2-en-1-yl)sulfanyl]-6-fluoro-1,3-benzothiazol-5-yl)-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.01024

5-tert-butyl-3-(6-chloro-2-[(3,3-dichloroprop-2-en-1-yl)sulfanyl]-1,3-benzothiazol-5-yl)-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.00311

5-tert-butyl-3-[6-chloro-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.00861

5-tert-butyl-3-[6-chloro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.0214

5-tert-butyl-3-[6-chloro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-thiadiazol-2(3H)-one

-

pH and temperature not specified in the publication

0.01592

5-tert-butyl-3-[6-fluoro-2-(prop-2-en-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-oxadiazol-2(3H)-one

-

pH 7.4, temperature not specified in the publication

0.00973

5-tert-butyl-3-[6-fluoro-2-(prop-2-yn-1-ylsulfanyl)-1,3-benzothiazol-5-yl]-1,3,4-thiadiazol-2(3H)-one

-

pH and temperature not specified in the publication

0.00011 - 0.00472

acifluorfen

10 entries

0.0008

cobalt-protoporphyrin

-

noncompetitive

0.00101

ethyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00158

ethyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00696

ethyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00142

ethyl 2-((5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)sulfanyl)propanoate

-

pH 7.4, temperature not specified in the publication

0.00009

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)-2-phenylacetate

-

0.00006

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate

-

0.00011

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

0.000045

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate

-

0.00012

ethyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

0.00135

ethyl 2-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate

-

pH 7.4, temperature not specified in the publication

0.00154

ethyl 2-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)-2-methylpropanoate

-

pH 7.4, temperature not specified in the publication

0.00813

ethyl 2-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

pH 7.4, temperature not specified in the publication

0.04807

ethyl 2-[2-chloro-4-fluoro-5-(1-hydroxy-3-oxooctahydro-2H-isoindol-2-yl)phenoxy]propanoate

-

pH not specified in the publication, temperature not specified in the publication

11.02

ethyl 2-[2-chloro-5-(1,3-dioxooctahydro-2H-isoindol-2-yl)-4-fluorophenoxy]propanoate

-

pH not specified in the publication, temperature not specified in the publication

0.00169

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

pH 7.4, temperature not specified in the publication

0.00025

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

pH 7.4, temperature not specified in the publication

0.00032

ethyl 3-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

pH 7.4, temperature not specified in the publication

0.00169

ethyl 3-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)propanoate

-

pH 7.4, temperature not specified in the publication

0.00202

ethyl 4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

pH 7.4, temperature not specified in the publication

0.0007

ethyl 4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

pH 7.4, temperature not specified in the publication

0.00583

ethyl 4-([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)butanoate

-

pH 7.4, temperature not specified in the publication

0.1238

ethyl [2-chloro-4-fluoro-5-(1-hydroxy-3-oxooctahydro-2H-isoindol-2-yl)phenoxy]acetate

-

pH not specified in the publication, temperature not specified in the publication

0.01524

ethyl [2-chloro-5-(1,3-dioxooctahydro-2H-isoindol-2-yl)-4-fluorophenoxy]acetate

-

pH not specified in the publication, temperature not specified in the publication

0.00034

ethyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.00748

methyl (2E)-4-([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)but-2-enoate

-

pH 7.4, temperature not specified in the publication

0.00107

methyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00399

methyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00746

methyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00122

methyl 2-((5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl)thio)acetate

-

pH 7.5, 22°C, recombinant enzyme

0.0000398

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate

-

0.000049

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-2-methyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

-

0.0000081

methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)butanoate

-

0.00225

methyl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00305

methyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.00392

methyl [[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.000034

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)-3-(trifluoromethoxy)benzamide

-

0.000089

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-4-fluorophenylcarbamoyl)benzamide

-

0.0062

N-(2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)phenylcarbamoyl)benzamide

-

0.00029

phenyl 2-[[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.132

phenyl 2-[[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.0344

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

pH and temperature not specified in the publication

0.012

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH and temperature not specified in the publication

0.00346

phenyl 2-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

pH and temperature not specified in the publication

0.0435

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

pH and temperature not specified in the publication

0.173

phenyl 2-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH and temperature not specified in the publication

0.00166

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]-2-methylpropanoate

-

pH 7.5, 22°C, recombinant enzyme

0.0008

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.0859

phenyl 2-[[6-chloro-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.00011

phenyl 3-[[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.00552

phenyl 3-[[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.00128

phenyl 3-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH and temperature not specified in the publication

0.00589 - 0.00926

phenyl 3-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]propanoate

0.0275

phenyl 3-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH and temperature not specified in the publication

0.00032

phenyl 3-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.00376

phenyl 3-[[6-chloro-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]propanoate

-

pH 7.5, 22°C, recombinant enzyme

0.0177

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

pH and temperature not specified in the publication

0.00867

phenyl 4-[[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

pH and temperature not specified in the publication

2.45

phenyl 4-[[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

pH and temperature not specified in the publication

0.00075

phenyl 4-[[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]butanoate

-

pH 7.5, 22°C, recombinant enzyme

0.00025

phenyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00582

phenyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.0156

phenyl [[6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.00166

phenyl [[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00217

propan-2-yl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00117

propan-2-yl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00597

propan-2-yl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00021

propan-2-yl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.0015

propan-2-yl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00126

propan-2-yl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.00098

propyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.0007

propyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.0031

propyl ([6-bromo-5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00028

propyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00124

propyl [[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00131

propyl [[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH and temperature not specified in the publication

0.00008

S-(5-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-6-fluorobenzothiazol-2-yl) O-methyl carbonothioate

-

pH 7.5, 22°C, recombinant enzyme

0.00051

S-[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

pH 7.5, 22°C, recombinant enzyme

0.00033

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

pH 7.4, temperature not specified in the publication

0.0013

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

pH 7.4, temperature not specified in the publication

0.00072

S-[5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-methyl carbonothioate

-

pH 7.4, temperature not specified in the publication

0.0002

S-[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

pH and temperature not specified in the publication

0.00004

S-[5-(5-tert-butyl-2-oxo-1,3,4-thiadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl] O-ethyl carbonothioate

-

pH and temperature not specified in the publication

0.00052

S-[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl] O-methyl carbonothioate

-

pH 7.5, 22°C, recombinant enzyme

0.00047

S-[6-chloro-5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-1,3-benzothiazol-2-yl] O-phenyl carbonothioate

-

pH 7.5, 22°C, recombinant enzyme

0.00072

sulfentrazone

0.00084

tert-butyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-chloro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00159

tert-butyl ([5-(5-tert-butyl-2-oxo-1,3,4-oxadiazol-3(2H)-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl)acetate

-

pH 7.4, temperature not specified in the publication

0.00018

tert-butyl [[5-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)-6-fluoro-1,3-benzothiazol-2-yl]sulfanyl]acetate

-

pH 7.5, 22°C, recombinant enzyme

0.00112

acifluorfen

Homo sapiens

-

at pH 7.2 and 37°C

0.1

Atrazine

Homo sapiens

-

IC50 above 0.1 mM, at pH 7.2 and 37°C

0.00015

butafenacil

Homo sapiens

-

at pH 7.2 and 37°C

0.00042

chlornitrofen

Homo sapiens

-

at pH 7.2 and 37°C

0.1

chlortoluron, ethyl (2,4-dichloro-5-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]phenoxy)acetate, ethyl (2,4-dichloro-5-[[(Z)-[4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate, ethyl (2,4-dichloro-5-[[(Z)-[6-fluoro-4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate, ethyl (2,4-dichloro-5-[[(Z)-[6-nitro-4-oxo-2-[(propan-2-yl)oxy]-2H-1-benzopyran-3(4H)-ylidene]methyl]amino]phenoxy)acetate, ethyl [2,4-dichloro-5-[(E)-(2,5-dihydroxybenzylidene)amino]phenoxy]acetate, ethyl [2,4-dichloro-5-[(E)-(2-hydroxy-3-methoxybenzylidene)amino]phenoxy]acetate, ethyl [2,4-dichloro-5-[(E)-(2-hydroxy-4-methylbenzylidene)amino]phenoxy]acetate, ethyl [2,4-dichloro-5-[(E)-(5-chloro-2-hydroxybenzylidene)amino]phenoxy]acetate

Homo sapiens

-

IC50 above 0.1 mM, at pH 7.2 and 37°C

-

0.00011

formesafen

Homo sapiens

-

at pH 7.2 and 37°C

-

0.00033

lactofen

Homo sapiens

-

at pH 7.2 and 37°C

0.00386

methyl 3-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-sulfanylidene-1,3,5-triazinan-1-yl)-4-fluorophenyl]-5-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

Homo sapiens

-

at pH 7.2 and 37°C

-

0.00085

oxadiargyl

Homo sapiens

-

at pH 7.2 and 37°C

0.00192

oxadiazon

Homo sapiens

-

at pH 7.2 and 37°C

0.00013

oxyfluorfen

Homo sapiens

-

at pH 7.2 and 37°C

0.00025

saflufenacil

Homo sapiens

-

at pH 7.2 and 37°C

additional information

Homo sapiens

IC50 values are determined by measuring hPPO activity over a range of inhibitor concentrations at a single substrate concentration. IC50 values are calculated by fitting data to a single binding site model, overview

745134

-

0.0023

-

recombinant wild-type enzyme

0.62

-

recombinant mutant Y348C

1.26

-

recombinant mutant R168C

2.69

-

recombinant mutant R59K

3.04

-

recombinant mutant G14A

7.15

-

recombinant wild-type enzyme

additional information

7.4

assay at

7.2

-

7.4

-

assay at

712221, 726346

7.5

-

assay at

7.8

-

mutant Y348C

8.2

-

except for mutant Y348C

37

assay at

22

-

assay at room temperature

-

-

-

-

-

-

-

-

from healthy women and porphyria (VP) patient women, enzyme PPOX activity is reduced in the latter

serous cells

-

-

parietal cells

interstitial cells

-

-

-

-

additional information

mitochondrial inner membrane

analysis of mitochondrial targeting sequences of wild-type and mutant enzymes, overview

5743

mitochondrial inner membrane

-

malfunction

antioxidants restore protoporphyrinogen oxidase in variegate porphyria patients showing accumulation of heme precursors and a low rate of heme biosynthesis. Lymphocytes from variegate porphyria patients show reduced PPOX expression and present a greater susceptibility to producing H2O2 and impaired H2O2 detoxifying mechanisms. Supplementation with vitamins E and C restores PPOX expression in variegate porphyria patients and enhances glutathione reductase (GRd) and superoxide dismutase (SOD) activities. Phenotype, overview

metabolism

malfunction

metabolism

additional information

-

substrate binding model, molecular docking studies, overview. The protogen is surrounded by R97, L166, R168, G169, V170, F331, L334, M368, and FAD in hPPO. Ring A of protogen interacts with R168 and is kept in position by hydrophobic interaction with M368. Ring B of protogen is sandwiched between hPPO residue V170 and FAD

P50336 pBLAST

PPOX_HUMAN

477

0

50765

Swiss-Prot

Show Sequence

Mitochondrion (Reliability: 4)

100000

-

gel filtration

391004, 391007

32000

-

gel filtration

51000

4 entries

?

-

x * 51000, SDS-PAGE

dimer

additional information

-

secondary structure analysis, wild-type and mutant enzymes, structure/function relationship mutant R59W

additional information

crystal structure analysis

-

F331A

site-directed mutagenesis, calculation of free binding energy shifts

F331T

site-directed mutagenesis, calculation of free binding energy shifts

G169A

site-directed mutagenesis, calculation of free binding energy shifts

I12T

naturally occurring mutation in a finnish variegate porphyria patient, genotype-phenotype analysis, highly reduced activity

L166N

site-directed mutagenesis, calculation of free binding energy shifts

L334V

site-directed mutagenesis, calculation of free binding energy shifts

L401F

naturally occurring mutation in a finnish variegate porphyria patient, genotype-phenotype analysis, inactive mutant

M368K

site-directed mutagenesis, calculation of free binding energy shifts

M368Q

site-directed mutagenesis, calculation of free binding energy shifts

R152C

naturally occurring mutation in a finnish variegate porphyria patient, genotype-phenotype analysis, highly reduced activity

R168S

site-directed mutagenesis, calculation of free binding energy shifts

R97G

site-directed mutagenesis, calculation of free binding energy shifts

V170T

site-directed mutagenesis, calculation of free binding energy shifts

A172V

-

site-directed mutagenesis, 99.8% reduced activity compared to the wild-type enzyme, 99% complementation of enzyme-deficient Escherichia coli strain SAS38X

A433P

-

reduced activity

391007

D143V

-

site-directed mutagenesis, 99.6% reduced activity compared to the wild-type enzyme, 89% complementation of enzyme-deficient Escherichia coli strain SAS38X

D349A

-

the mutant enzyme maintains 8.05% of wild type activity

D349E

-

the mutant enzyme maintains 84.78% of wild type activity

D349R

-

the mutant enzyme maintains 2.48% of wild type activity

del281H

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

F331A

-

site-directed mutagenesis of ring A, the mutant shows decreased activity compared to the wild-type enzyme

F331T

-

site-directed mutagenesis of ring A, the mutant shows increased activity compared to the wild-type enzyme

G11A

-

site-directed mutagenesis, 0.02% activity compared to the wild-type enzyme

G14A

-

site-directed mutagenesis, 42.6% activity compared to the wild-type enzyme

G169A

-

site-directed mutagenesis of ring C, the mutant shows decreased activity compared to the wild-type enzyme

G232R

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

G40E

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

G453R

-

site-directed mutagenesis, nearly inactive mutant, but 89% complementation of enzyme-deficient Escherichia coli strain SAS38X

G453V

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

G9A

-

site-directed mutagenesis, 0.52% activity compared to the wild-type enzyme

H20A

-

targets the mitochondrion

H20E

-

targets the mitochondrion

H20G

-

targets the mitochondrion

H20K

-

targets the mitochondrion

H20P

H20S

-

targets the mitochondrion

I283N

-

naturally occurring mutation involved in pathology of variegate porphyria

655700

L154P

-

site-directed mutagenesis, 99.6% reduced activity compared to the wild-type enzyme, 93% complementation of enzyme-deficient Escherichia coli strain SAS38X

L15F

-

site-directed mutagenesis, 97.4% reduced activity compared to the wild-type enzyme, 49% complementation of enzyme-deficient Escherichia coli strain SAS38X

L166N

-

site-directed mutagenesis of ring C, the mutant shows decreased activity compared to the wild-type enzyme

L295P

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

L334V

-

site-directed mutagenesis of ring A, the mutant shows highly increased activity compared to the wild-type enzyme

L444P

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

L73P

-

site-directed mutagenesis, 97.6% reduced activity compared to the wild-type enzyme, complete complementation of enzyme-deficient Escherichia coli strain SAS38X

L85P

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

M368K

-

site-directed mutagenesis of ring A, the mutant shows increased activity compared to the wild-type enzyme

M368Q

-

site-directed mutagenesis of ring A, the mutant shows decreased activity compared to the wild-type enzyme

R152C

-

site-directed mutagenesis, 99.4% reduced activity compared to the wild-type enzyme, 86% complementation of enzyme-deficient Escherichia coli strain SAS38X

R168C

R168H

-

site-directed mutagenesis, 99.8% reduced activity compared to the wild-type enzyme, 68% complementation of enzyme-deficient Escherichia coli strain SAS38X

R168S

-

site-directed mutagenesis of ring A, the mutant shows decreased activity compared to the wild-type enzyme

R38P

-

site-directed mutagenesis, 99.2% reduced activity compared to the wild-type enzyme, 59% complementation of enzyme-deficient Escherichia coli strain SAS38X

R59A

-

the mutant enzyme maintains 44.13% of wild type activity

R59E

-

the mutant enzyme maintains 22.72% of wild type activity

R59I

-

site-directed mutagenesis, 1.5% activity compared to the wild-type enzyme

R59K

R59S

-

site-directed mutagenesis, 2.6% activity compared to the wild-type enzyme

R59W

5 entries

R97G

-

site-directed mutagenesis of ring A, the mutant shows increased activity compared to the wild-type enzyme

S350P

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

T366A

-

the mutant enzyme maintains 65.45% of wild type activity

V158M

-

site-directed mutagenesis, 91.8% reduced activity compared to the wild-type enzyme, 97% complementation of enzyme-deficient Escherichia coli strain SAS38X

V170T

-

site-directed mutagenesis of ring B, the mutant shows increased activity compared to the wild-type enzyme

V282D

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

V290L

-

site-directed mutagenesis, 98.8% reduced activity compared to the wild-type enzyme, 93% complementation of enzyme-deficient Escherichia coli strain SAS38X

V335G

-

site-directed mutagenesis, inactive mutant, no complementation of enzyme-deficient Escherichia coli strain SAS38X

V84G

-

site-directed mutagenesis, 99.8% reduced activity compared to the wild-type enzyme, 88% complementation of enzyme-deficient Escherichia coli strain SAS38X

Y348C

-

site-directed mutagenesis, 8.6% activity compared to the wild-type enzyme

additional information

7 entries

40

-

recombinant wild-type and mutants, stable at

47.6

-

50% inactivation of mutant R168C

50.2

-

50% inactivation of mutant Y348C

53

-

50% inactivation of mutant R59W

54.2

-

50% inactivation of mutant R59I

56.3

-

50% inactivation of mutant R59K

56.8

-

50% inactivation of recombinant wild-type enzyme

57

-

50% inactivation of mutant G14A

60.3

-

50% inactivation of mutant R59S

dithiothreitol stabilizes better than glutathione

-

4°C, stable for days, slow proteolysis

-

-

-

by gel filtration

-

cloned enzyme

-

391004, 391007, 391012

Ni-NTA column chromatography

-

Ni-NTA column chromatography and Superdex 200 gel filtration

-

recombinant His-tagged enzyme from Escherichia coli strain JM109 by nickel affinity chromatography

-

recombinant wild-type and mutant enzymes from Escherichia coli strain JM109, to homogeneity

-

DNA and amino acid sequence determination and analysis, expression of wild-type and mutant enzymes in Escherichia coli and as GFP-fusion proteins in COS-1 cells

gene PPOX, relative real-time RT-PCR enzyme expression analysis

744837

expressed in Escherichia coli BL21(DE3)pLysS cells

-

expressed in Escherichia coli JM109 cells

-

expressed in Oryza sativa chloroplasts

-

689568

expression of the His-tagged enzyme in Escherichia coli strain JM109

-

expression of wild-type and mutant enzymes in Escherichia coli enzyme-deficient strain SAS38X which is not able to grow without exogenously added heme, complementation study, comparison of missense mutations in the human PPOX gene with the equivalent positions of other species' genes

-

expression of wild-type and mutant enzymes in Escherichia coli strain JM109

-

gene PPOX, genetic analysis of variegate porphyria, VP, an acute hepatic porphyria, in Italy

-

in Escherichia coli

-

in Escherichia coli, His-tag inserted for purification

-

391004, 391007

overexpression in Escherichia coli JM109 cells

-

671294

wild-type and mutant cDNAs cloned into the pEGFP-N1 vector and transiently transfected into HepG2 cells

-

antioxidant vitamins increase PPOX expression in variegate porphyria patients

744837

renaturation and refolding after thermal denaturation and unfolding at 75°C by cooling to 15°C, pH 7.2

-

agriculture

-

the enzyme is a herbicidal target

analysis

-

advantages of the continuous spectrofluorimetric assay over the discontinuous assay is of importance for both the kinetic characterization of recombinant PPOs and the detection of low concentrations of this enzyme in biological samples, may be useful for assessing diminished PPO activities in variegate porphyria patient samples

671294

diagnostics

-

detection of the naturally occuring 1082-1083insC mutation in the PPOX gene is a genetic marker for variegate porphyria in humans

697206

medicine

-

variegate porphyria resulting from a deficiency in protoporphyrinogen oxidase

390981

Poulson, R.

The enzymic conversion of protoporphyrinogen IX to protoporphyrin IX in mammalian mitochondria

J. Biol. Chem.

251

3730-3733

1976

Saccharomyces cerevisiae, Homo sapiens, Rattus norvegicus

6461

Camadro, J.M.; Abraham, N.G.; Levere, R.D.

Kinetic properties of the membrane-bound human liver mitochondrial protoporphyrinogen oxidase

Arch. Biochem. Biophys.

242

206-212

1985

Homo sapiens

4051500

391002

Meissner, P.N.; Dailey, T.A.; Hift, R.J.; Ziman, M.; Corrigall, A.V.; Roberts, A.G.; Meissner, D.M.; Kirsch, R.E.; Dailey, H.A.

A R59W mutation in human protoporphyrinogen oxidase results in decreased enzyme activity and is prevalent in South Africans with variegate porphyria

Nature Genet.

13

95-97

1996

Homo sapiens

8673113

391004

Dailey, T.A.; Dailey, H.A.

Human protoporphyrinogen oxidase: Expression, purification, and characterization of the cloned enzyme

Protein Sci.

5

98-105

1996

Homo sapiens

8771201

391007

Dailey, H.A.; Dailey, T.A.

Characteristics of human protoporphyrinogen oxidase in controls and variegate porphyrias

Cell. Mol. Biol.

43

67-73

1997

Homo sapiens

9074790

391012

Birchfield, N.B.; Latli, B.; Casida, J.E.

Human protoporphyrinogen oxidase: Relation between the herbicide binding site and the flavin cofactor

Biochemistry

37

6905-6910

1998

Homo sapiens

9578577

Maneli, M.H.; Corrigall, A.V.; Klump, H.H.; Davids, L.M.; Kirsch, R.E.; Meissner, P.N.

Kinetic and physical characterisation of recombinant wild-type and mutant human protoporphyrinogen oxidases

Biochim. Biophys. Acta

1650

10-21

2003

Homo sapiens

12922165

Morgan, R.R.; da, S.V.; Puy, H.; Deybach, J.C.; Elder, G.H.

Functional studies of mutations in the human protoporphyrinogen oxidase gene in variegate porphyria

Cell. Mol. Biol.

48

79-82

2002

Homo sapiens

11929051

von und zu Fraunberg, M.; Timonen, K.; Mustajoki, P.; Kauppinen, R.

Clinical and biochemical characteristics and genotype-phenotype correlation in Finnish variegate porphyria patients

Eur. J. Hum. Genet.

10

649-657

2002

Homo sapiens (P50336), Homo sapiens

12357337

655700

D'Amato, M.; Bonuglia, M.; Barile, S.; Griso, D.; Macri, A.; Biolcati, G.

Genetic analysis of variegate porphyria (VP) in Italy: identification of six novel mutations in the protoporphyrinogen oxidase (PPOX) gene

Hum. Mutat.

21

448

2003

Homo sapiens

12655566

671294

Shepherd, M.; Dailey, H.A.

A continuous fluorimetric assay for protoporphyrinogen oxidase by monitoring porphyrin accumulation

Anal. Biochem.

344

115-121

2005

Aquifex aeolicus, Homo sapiens, Mus musculus, Myxococcus xanthus

16039600

Davids, L.M.; Corrigall, A.V.; Meissner, P.N.

Mitochondrial targeting of human protoporphyrinogen oxidase

Cell Biol. Int.

30

416-426

2006

Homo sapiens

16621625

686939

de Vooght, K.M.; van Wijk, R.; van Solinge, W.W.

GATA-1 binding sites in exon 1 direct erythroid-specific transcription of PPOX

Gene

409

83-91

2008

Homo sapiens (P50336), Homo sapiens

18191920

689568

Jung, S.; Lee, H.J.; Lee, Y.; Kang, K.; Kim, Y.S.; Grimm, B.; Back, K.

Toxic tetrapyrrole accumulation in protoporphyrinogen IX oxidase-overexpressing transgenic rice plants

Plant Mol. Biol.

67

535-546

2008

Homo sapiens

18437505

Zhang, L.; Hao, G.F.; Tan, Y.; Xi, Z.; Huang, M.Z.; Yang, G.F.

Bioactive conformation analysis of cyclic imides as protoporphyrinogen oxidase inhibitor by combining DFT calculations, QSAR and molecular dynamic simulations

Bioorg. Med. Chem.

17

4935-4942

2009

Homo sapiens

19540767

697205

Corrigall, A.V.; Campbell, J.A.; Siziba, K.; Kirsch, R.E.; Meissner, P.N.

The expression of protoporphyrinogen oxidase in human tissues

Cell. Mol. Biol.

55

89-95

2009

Homo sapiens (P50336), Homo sapiens

19656456

697206

Van Tuyll Van Serooskerke, A.M.; Schneider-Yin, X.; Schimmel, R.J.; Bladergroen, R.S.; Poblete-Gutierrez, P.; Barman, J.; van Geel, M.; Frank, J.; Minder, E.I.

Identification of a recurrent mutation in the protoporphyrinogen oxidase gene in Swiss patients with variegate porphyria: clinical and genetic implications

Cell. Mol. Biol.

55

96-101

2009

Homo sapiens

19656457

Zhang, L.; Tan, Y.; Wang, N.X.; Wu, Q.Y.; Xi, Z.; Yang, G.F.

Design, syntheses and 3D-QSAR studies of novel N-phenyl pyrrolidin-2-ones and N-phenyl-1H-pyrrol-2-ones as protoporphyrinogen oxidase inhibitors

Bioorg. Med. Chem.

18

7948-7956

2010

Amaranthus retroflexus, Brassica juncea, Chenopodium album, Digitaria sanguinalis, Echinochloa crus-galli, Homo sapiens, Setaria viridis, Eclipta prostrata

20934343

Jiang, L.L.; Tan, Y.; Zhu, X.L.; Wang, Z.F.; Zuo, Y.; Chen, Q.; Xi, Z.; Yang, G.F.

Design, synthesis, and 3D-QSAR analysis of novel 1,3,4-oxadiazol-2(3H)-ones as protoporphyrinogen oxidase inhibitors

J. Agric. Food Chem.

58

2643-2651

2010

Homo sapiens

19954223

Zuo, Y.; Yang, S.G.; Jiang, L.L.; Hao, G.F.; Wang, Z.F.; Wu, Q.Y.; Xi, Z.; Yang, G.F.

Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors

Bioorg. Med. Chem.

20

296-304

2012

Homo sapiens

22130420

Jiang, L.L.; Zuo, Y.; Wang, Z.F.; Tan, Y.; Wu, Q.Y.; Xi, Z.; Yang, G.F.

Design and syntheses of novel N-(benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and N-(benzothiazol-5-yl)isoindoline-1,3-dione as potent protoporphyrinogen oxidase inhibitors

J. Agric. Food Chem.

59

6172-6179

2011

Homo sapiens

21517076

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

23935953

744837

Ferrer, M.D.; Tauler, P.; Sureda, A.; Palacin, C.; Tur, J.A.; Pons, A.

Antioxidants restore protoporphyrinogen oxidase in variegate porphyria patients

Eur. J. Clin. Invest.

43

668-678

2013

Homo sapiens (P50336), Homo sapiens

23601071

745134

Hao, G.F.; Tan, Y.; Xu, W.F.; Cao, R.J.; Xi, Z.; Yang, G.F.

Understanding resistance mechanism of protoporphyrinogen oxidase-inhibiting herbicides insights from computational mutation scanning and site-directed mutagenesis

J. Agric. Food Chem.

62

7209-7215

2014

Homo sapiens (P50336)

24983412

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)

23935953

Wang, B.; Zhang, Z.; Zhu, H.; Niu, C.; Wen, X.; Xi, Z.

The hydrogen bonding network involved Arg59 in human protoporphyrinogen IX oxidase is essential for enzyme activity

Biochem. Biophys. Res. Commun.

557

20-25

2021

Homo sapiens

33857841

764914

Barker, A.L.; Barnes, H.; Dayan, F.E.

Conformation of the intermediates in the reaction catalyzed by protoporphyrinogen oxidase An in silico analysis

Int. J. Mol. Sci.

21

9495

2020

Homo sapiens

33327448