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(S)-dihydroorotate + 1,4-naphthoquinone
orotate + 1,4-naphthoquinol
-
-
-
-
?
(S)-dihydroorotate + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
orotate + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
-
-
-
-
?
(S)-dihydroorotate + 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone
orotate + reduced 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone
-
-
-
-
?
(S)-dihydroorotate + 2,5-dimethyl-p-benzoquinone
orotate + 2,5-dimethyl-p-benzoquinol
-
-
-
-
?
(S)-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
(S)-dihydroorotate + coenzyme Q
orotate + reduced coenzyme Q
-
-
-
-
?
(S)-dihydroorotate + decylubiquinone
orotate + decylubiquinol
-
-
-
-
?
(S)-dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
Q02172;
-
-
-
?
(S)-dihydroorotate + oxidized 2,6-dichloroindophenol
orotate + reduced 2,6-dichloroindophenol
-
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + reduced ubiquinone
-
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
(S)-dihydroorotate + ubiquinone-30
orotate + ubiquinol-30
-
-
-
-
?
(S)-dihydroorotate + ubiquinone-50
orotate + ubiquinol-50
-
-
-
-
?
benzyl-(S)-dihydroorotate + acceptor
benzyl orotate + reduced acceptor
-
-
-
-
?
dihydroorotate + 2,3-dimethoxy-5-methyl-1,4-benzoquinone
orotate + reduced 2,3-dimethoxy-5-methyl-1,4-benzoquinone
-
-
-
?
dihydroorotate + 2,5-dimethyl-p-benzoquinone
orotate + reduced 2,5-dimethyl-p-benzoquinone
95% the rate of decylubiquinone, wild-type, 75% the rate of decylubiquinone, DELTA1-75 mutant
-
-
?
dihydroorotate + 2,5-dimethylbenzoquinone
orotate + reduced 2,5-dimethylbenzoquinone
-
84% of the rate with decylubiquinone
-
-
?
dihydroorotate + 2,6-dichloroindophenol
orotate + reduced 2,6-dichloroindophenol
-
-
-
?
dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
dihydroorotate + acceptor
orotate + reduced acceptor
dihydroorotate + coenzyme Q
orotate + reduced coenzyme Q
-
coenzyme OD possesses a decyl tail
-
-
?
dihydroorotate + coenzyme Q1
orotate + reduced coenzyme Q1
-
coenzyme Q1 possesses a prenyl tail
-
-
?
dihydroorotate + coenzyme QD
orotate + reduced coenzyme QD
-
coenzyme QD possesses a decyl tail
-
-
?
dihydroorotate + CoQ0
orotate + reduced CoQo
102% the rate of decylubiquinone, wild-type, 67% the rate of decylubiquinone, DELTA1-75 mutant
-
-
?
dihydroorotate + decylplastoquinone
orotate + reduced decylplastoquinone
dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
dihydroorotate + menadione
orotate + reduced menadione
dihydroorotate + O2
orotate + H2O2
-
-
-
-
?
dihydroorotate + potassium hexacyanoferrate(III)
orotate + reduced potassium hexacyanoferrate(III)
-
-
-
?
dihydroorotate + ubiquinone 30
orotate + reduced ubiquinone 30
-
-
-
?
dihydroorotate + ubiquinone 50
orotate + reduced ubiquinone 50
-
-
-
?
dihydroorotate + ubiquinone-0
orotate + reduced ubiquinone-0
-
80% of the rate with decylubiquinone
-
-
?
dihydroorotate + ubiquinone-10
orotate + reduced ubiquinone-10
-
59% of the rate with decylubiquinone
-
-
?
dihydroorotate + ubiquinone-50
orotate + reduced ubiquinone-50
83% the rate of decylubiquinone, wild-type, 76% the rate of decylubiquinone, DELTA1-75 mutant
-
-
?
ethyl-dihydroorotate + acceptor
ethyl-orotate + reduced acceptor
-
-
-
-
?
L-dihydroorotate + 2,6-dichloroindophenol
orotate + ?
-
-
-
-
?
L-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
L-dihydroorotate + decylubiquinone
orotate + ?
-
-
-
-
?
L-dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
L-dihydroorotate + FMN
orotate + FMNH2
L-dihydroorotate + ubiquinone-0
orotate + reduced ubiquinone-0
-
-
-
?
L-dihydroorotate + ubiquinone-4
orotate + reduced ubiquinone-4
-
-
-
?
L-dihydroorotate + ubiquinone-6
orotate + reduced ubiquinone-6
L-dihydroorotate + vitamin K3
orotate + reduced vitamin K3
-
-
-
?
methyl-dihydroorotate + acceptor
methyl-orotate + reduced acceptor
-
-
-
-
?
tert-butyl-dihydroorotate + acceptor
tert-butyl-orotate + reduced acceptor
-
-
-
-
?
additional information
?
-
(S)-dihydroorotate + 2,6-dichlorophenolindophenol

orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
(S)-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
Q02172;
-
-
-
?
(S)-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
(S)-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
(S)-dihydroorotate + acceptor

orotate + reduced acceptor
-
fumarate and menadione as electron acceptors
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
reduction of a number of substrates: fumatate, coenzyme ubiquinone-0 and menadione
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
uses ubiquinone as electron acceptor
-
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
with ubiquinone-0, 2,6-dichlorophenolindophenol, menadione, decylubiquinone, fumarate and O2 as electron acceptor
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in synthesis of pyrimidine nucleotides
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in synthesis of pyrimidine nucleotides
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in synthesis of pyrimidine nucleotides
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
ubiquinone-6 tested as electron acceptor
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
with ubiquinone-0, 2,6-dichlorophenolindophenol, menadione, decylubiquinone, fumarate and O2 as electron acceptor
-
?
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in synthesis of pyrimidine nucleotides
-
?
(S)-dihydroorotate + ubiquinone

orotate + ubiquinol
-
-
-
-
-
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
reaction studied with menadione, O2 and ferricyanide
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
decylubiquinone as electron acceptor
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
six-step biosynthesis of pyrimidine uridine monophosphate
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth step in synthesis of uridine 5'-monophosphate
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
ubiquinone-6, ubiquinone-7, ubiquinone-9 and ubiquinone-10 maximize enzyme activity
-
-
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth step in synthesis of uridine 5'-monophosphate
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
-
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
fourth enzyme in pyrimidine synthesis
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
six-step biosynthesis of pyrimidine uridine monophosphate
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
-
-
ir
dihydroorotate + 2,6-dichlorophenolindophenol

orotate + reduced 2,6-dichlorophenolindophenol
-
33% of the rate with decylubiquinone
-
-
?
dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
?
dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
dihydroorotate + acceptor

orotate + reduced acceptor
-
acceptor: quinones
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: coenzyme Q6
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
not acceptor: oxygen
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: menadione
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor coenzyme Q7
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: menadione
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: fumarate, coenzyme Q10
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
mechanism and pH-dependence of reaction
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: 2,6-dichlorophenolindophenol
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: menaquinone
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: ubiquinone
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
reaction intermediates, mechanism, pH-dependence of reaction
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
physiological electron acceptor: ubiquinone (aerobic conditions), menaquinone (anaerobic conditions)
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor (low activity): 1,4-naphthoquinone, 5,8-hydroxy-naphthoquinone, juglon, plumbagin, polyporic acid
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: ubiquinone
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: 2,6-dichlorophenolindophenol
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: quinones
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
not acceptor: oxygen
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
cytochrome b, cytochrome c, pyridine nucleotides (NAD+, NADP+) cannot serve as electron acceptors
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: quinones
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
-
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
-
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: 2,6-dichlorophenolindophenol
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptors: e.g. phenazine methosulfate
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor (low activity): 1,4-naphthoquinone, 5,8-hydroxy-naphthoquinone, juglon, plumbagin, polyporic acid
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: ubiquinone
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: oxygen, slowly
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in pyrimidine biosynthesis
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
acceptor: ubiquinone
-
-
?
dihydroorotate + decylplastoquinone

orotate + reduced decylplastoquinone
95% the rate of decylubiquinone, wild-type, 104% the rate of decylubiquinone, DELTA1-75 mutant
-
-
?
dihydroorotate + decylplastoquinone
orotate + reduced decylplastoquinone
-
78% of the rate with decylubiquinone
-
-
?
dihydroorotate + decylubiquinone

orotate + reduced decylubiquinone
-
-
-
?
dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
-
-
-
?
dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
-
-
-
-
?
dihydroorotate + menadione

orotate + reduced menadione
82% the rate of decylubiquinone, wild-type, 78% the rate of decylubiquinone, DELTA1-75 mutant
-
-
?
dihydroorotate + menadione
orotate + reduced menadione
-
39% of the rate with decylubiquinone
-
-
?
L-dihydroorotate + 2,6-dichlorophenolindophenol

orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
-
L-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
L-dihydroorotate + decylubiquinone

orotate + reduced decylubiquinone
-
-
-
-
-
L-dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
-
-
-
-
?
L-dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
-
-
-
?
L-dihydroorotate + FMN

orotate + FMNH2
-
-
-
-
?
L-dihydroorotate + FMN
orotate + FMNH2
-
DHODH catalyzes the FMN-dependent oxidation of dihydroorotate to produce orotic acid. Two separate half reactions are required to complete the catalytic cycle: 1. oxidation of dihydroorotate driven by the reduction of FMN and, 2. reoxidation of FMNH2 to regenerate the active enzyme
-
-
?
L-dihydroorotate + FMN
orotate + FMNH2
-
-
-
-
?
L-dihydroorotate + FMN
orotate + FMNH2
-
DHODH catalyzes the FMN-dependent oxidation of dihydroorotate to produce orotic acid. Two separate half reactions are required to complete the catalytic cycle: 1. oxidation of dihydroorotate driven by the reduction of FMN and, 2. reoxidation of FMNH2 to regenerate the active enzyme
-
-
?
L-dihydroorotate + ubiquinone-6

orotate + reduced ubiquinone-6
-
-
-
-
-
L-dihydroorotate + ubiquinone-6
orotate + reduced ubiquinone-6
-
-
-
-
-
L-dihydroorotate + ubiquinone-6
orotate + reduced ubiquinone-6
-
-
-
-
-
L-dihydroorotate + ubiquinone-6
orotate + reduced ubiquinone-6
-
-
-
?
additional information

?
-
-
not substrate: 1-methyl-(S)-dihydroorotate, 3-methyl-dihydroorotate, 1,3-dimethyldihydroorotate
-
-
-
additional information
?
-
-
fumarate and NAD are inadequate electron acceptors for full-length DHODH and N-terminally truncated DHODH
-
-
-
additional information
?
-
fumarate and NAD are inadequate electron acceptors for full-length DHODH and N-terminally truncated DHODH
-
-
-
additional information
?
-
-
computational method to investigate potential proton relay pathways in the active site of the enzyme
-
-
-
additional information
?
-
-
fumarate is a poor electron acceptor
-
-
-
additional information
?
-
-
enzyme has methylviologen-fumarate reductase activity
-
-
-
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(1-(5-cyclopropylpyrimidin-2-yl)-3-isopropoxy-5-methyl-1H-pyrazol-4-yl)(phenyl)methanol
-
-
-
(2,3-difluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(2,5-difluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(2,6-difluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(2-chloro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(2-fluoro-4-methyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(2E)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
-
50% inhibition at 0.000435 mM
(2E)-2-cyano-N-(2',3-dichloro[1,1'-biphenyl]-4-yl)-3-hydroxybut-2-enamide
-
-
(2E)-N-(3-chloro-2'-methoxy[1,1'-biphenyl]-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
-
(2E)-N-[2'-chloro-3-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-2-cyano-3-hydroxybut-2-enamide
-
-
(2Z)-2-cyano-3-cyclopropyl-3-hydroxy-N-[4-(trifluoromethyl)phenyl]prop-2-enamide
-
(2Z)-2-cyano-N-(2',3-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
(2Z)-2-cyano-N-(2,2'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
(2Z)-2-cyano-N-(2,3'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
(2Z)-2-cyano-N-(3'-ethoxybiphenyl-4-yl)-3-hydroxybut-2-enamide
-
(2Z)-N-(2'-chlorobiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
(2Z)-N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
(2Z)-N-(biphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
(2Z)-N-[2'-chloro-3-(trifluoromethyl)biphenyl-4-yl]-2-cyano-3-hydroxybut-2-enamide
-
(3,4-difluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3,4-dimethyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3,5-bis-trifluoromethyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3,5-difluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3-chloro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3-fluoro-4-methyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3-fluoro-4-trifluoromethyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(3-fluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-benzyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-bromo-3-trifluoromethyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-bromo-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-chloro-3-trifluoromethyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-chloro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-difluoromethoxy-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-fluoro-3-methyl-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-fluoro-phenyl)-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(4-methoxyphenyl)(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2,3,4,5,6-pentafluorophenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2,3,4-trifluoro-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2,3,5,6-tetrafluoro-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2,4,5-trifluoro-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2,4,6-trifluoro-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(2-trifluoromethyl-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(3-trifluoromethyl-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(4-methyl-3-trifluoromethylphenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(4-nitro-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(4-trifluoromethoxy-phenyl)-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-(4-trifluoromethyl-phenyl)-amine
-
DSM74
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-m-tolyl-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-naphthalen-2-yl-amine
-
DSM1, a potent triazolopyrimidine-based inhibitor of PfDHODH that shows greater than 4000fold selectivity for the malarial enzyme when compared to human DHODH
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-o-tolyl-amine
-
-
(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-p-tolyl-amine
-
-
1-(1-naphthyl)-3-[2-(trifluoromethyl)phenyl]urea
-
50% inhibition at 0.0004 mM, wild type, 0.00034 mM, mutant R265A, above 0.2, mutant H185A
1-(2-((3,4-dimethylphenyl)amino)-4-methylthiazol-5-yl)-ethanone
-
-
1-(2-((3-chloro-4-methylphenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
1-(2-((3-fluoro-4-methylphenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
1-(2-((4-(tert-butyl)phenyl)amino)-4-methylthiazol-5-yl)-ethanone
-
-
1-(2-((4-bromo-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
1-(2-((4-bromophenyl)amino)-4-methylthiazol-5-yl)-ethanone
-
-
1-(2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
1-(2-(anthracen-2-ylamino)-4-methylthiazol-5-yl)ethan-1-one
-
-
1-(2-methoxyphenyl)-3-(1-naphthyl)urea
-
50% inhibition at 0.00023 mM, wild type, 0.00024 mM, mutant R265A, 0.140, mutant H185A
1-(2-methoxyphenyl)-3-naphthalen-1-ylurea
1-(4-chlorophenyl)-3-quinolin-8-ylurea
-
50% inhibition at 0.00078 mM, wild type, 0.002 mM, mutant R265A, above 0.4, mutant H185A
1-(4-methyl-2-(naphthalen-2-ylamino)thiazol-5-yl)ethan-1-one
-
-
1-(4-methyl-2-(phenylamino)thiazol-5-yl)ethanone
-
-
1-hydroxy-2-dodecyl-4(1)quinolone
-
; competitive with regard to decylubiquinone, uncompetitive with regard to dihydroorotate
2,8-dimethyl-N-[4-(trifluoromethyl)phenyl]pyrrolo[1,2-a]pyrimidin-4-amine
-
-
2-(3-ethoxy-4-(2-fluorophenoxy)-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(3-ethoxy-5-methyl-4-(2-(trifluoromethyl)phenoxy)-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(3-ethoxy-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(3-ethoxy-5-methyl-4-(4-(trifluoromethyl)phenoxy)-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(3-ethoxy-5-methyl-4-phenoxy-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4'-tert-butyl-2-chloro-biphenyl-4-ylcarbamoyl)-cyclopent-1-enecarboxylic acid
-
50% inhibition at 0.000080 mM
2-(4-(2,3-dichlorophenoxy)-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,3-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,4-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,5-dichlorophenoxy)-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,5-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidin-4-ol
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-fluoropyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-methoxypyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-methylpyrimidin-4-ol
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-propylpyrimidin-4-ol
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-propylpyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-pyrimidine
-
-
-
2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidin-4-ol
-
-
-
2-(4-(2-bromophenoxy)-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(2-chlorophenoxy)-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-(3,5-dichlorophenoxy)-3-ethoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-benzyl-1-(5-ethylpyrimidin-2-yl)-5-methyl-1H-pyrazol-3-yloxy)ethanol
-
-
-
2-(4-benzyl-3-(2-(benzyloxy)ethoxy)-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-benzyl-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-cyclopropylpyrimidine
-
-
-
2-(4-benzyl-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)-5-ethylpyrimidine
-
-
-
2-(4-benzyl-3-methoxy-5-methyl-1H-pyrazol-1-yl)-5-cyclopropylpyrimidine
-
-
-
2-(4-benzyl-3-sec-butoxy-5-methyl-1H-pyrazol-1-yl)-5-cyclopropylpyrimidine
-
-
-
2-(4-benzyl-5-methyl-3-(pentan-3-yloxy)-1H-pyrazol-1-yl)-5-cyclopropylpyrimidine
-
-
-
2-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamino)-benzonitrile
-
-
2-([[2,3,5,6-tetrafluoro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000007 mM
2-([[2-chloro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000020 mM
2-([[2-chloro-4'-(dimethylamino)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00005 mM
2-([[3'-(trifluoromethoxy)-3-(trifluoromethyl)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000840 mM
2-([[3,5-difluoro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000033 mM
2-([[3-chloro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000290 mM
2-([[3-cyano-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000370 mM
2-([[3-fluoro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00028 mM
2-([[3-fluoro-4'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00570 mM
2-([[3-methyl-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000150 mM
2-([[3-nitro-3'-(trifluoromethoxy)biphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000390 mM
2-([[4'-(dimethylamino)-3,5-difluorobiphenyl-4-yl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00061 mM
2-([[4-(1-naphthyl)-2-(trifluoromethyl)phenyl]amino]carbonyl)cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000180 mM
2-cyano-3-(9-ethyl-9H-carbazol-3-ylamino)acrylic acid ethyl ester
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(cyano)phenyl]-propenamide
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(nitro)phenyl]-propenamide
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(trifluoromethyl)phenyl]-propenamide
2-cyano-3-hydroxy-N-(2',3,3'-trichlorobiphenyl-4-yl)but-2-enamide
-
-
2-hydroxyethylidene-cyano acetic acid 4-trifluoromethyl anilide
-
A177-1726, active derivative of human inhibitor leflunomide
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
2-methyl-3-nitro-N-[3-(trifluoromethyl)phenyl]benzamide
-
50% inhibition at 0.00008 mM, wild type, 0.00037 mM, mutant R265A, 0.120, mutant H185A
2-methyl-N-1-naphthyl-3-nitrobenzamide
-
50% inhibition at 0.00008 mM, wild type, 0.00048 mM, mutant R265A, 0.180, mutant H185A
2-[(2,5-dichlorophenyl)sulfanyl]-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
2-[(2,5-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
2-[(3,4-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
2-[(4-chlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
2-[(biphenyl-4-ylamino)carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00041 mM
2-[(E)-2-(2-methylphenyl)ethenyl]quinolin-4-ol
2-[[(2',3,5-trifluorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000045 mM
2-[[(2'-chloro-3,5-difluorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000018 mM
2-[[(2'-chlorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000225 mM
2-[[(2,3,5,6-tetrafluoro-2'-methoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000008 mM
2-[[(3'-ethoxy-3,5-difluorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000017 mM
2-[[(3,3'-dimethoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000170 mM
2-[[(3,5-difluoro-2',4'-dimethoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000090 mM
2-[[(3,5-difluoro-2'-methoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000042 mM
2-[[(3-chloro-2'-methoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000310 mM
2-[[(3-chloro-4'-methoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00840 mM
2-[[(3-fluoro-3'-hydroxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000610 mM
-
2-[[(3-fluoro-4'-methoxybiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00170 mM
2-[[(4'-bromo-2-chlorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000070 mM
2-[[(4'-bromo-3-chlorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.002900 mM
2-[[(4'-bromo-3-fluorobiphenyl-4-yl)amino]carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.000735 mM
2-[[(4-chlorophenyl)methyl]sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one
-
-
3-(4-benzyl-1-(5-ethylpyrimidin-2-yl)-5-methyl-1H-pyrazol-3-yloxy)-N,N-dimethylpropan-1-amine
-
-
-
3-hydroxy-2-(3,3-dichloroallyl)-1,4-naphthoquinone
4-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamino)-2-trifluoromethylbenzonitrile
-
-
4-benzyl-1-(5-cyclopropylpyrimidin-2-yl)-5-methyl-1H-pyrazol-3-ol
-
-
-
4-benzyl-1-(5-ethylpyrimidin-2-yl)-5-methyl-1H-pyrazol-3-ol
-
-
-
4-pentyl-1,3,4,10-tetrahydroacridin-9(2H)-one
4-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-(trifluoromethyl)benzonitrile
-
-
5,6-dimethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
5-(1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide
5-(1H-indol-1-yl)-N-propylthiophene-2-carboxamide
5-(2-methyl-1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide
5-(2-methyl-1H-indol-1-yl)-N-propylthiophene-2-carboxamide
5-(4-cyano-2-methyl-1H-benzimidazol-1-yl)-N-cyclopropylthiophene-2-carboxamide
-
-
5-(4-methylpiperazin-1-yl)-N-propylthiophene-2-carboxamide
5-(piperidin-1-yl)-N-propylthiophene-2-carboxamide
5-bromo-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-cyclopropyl-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-cyclopropyl-2-(4-(2-fluorobenzyl)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(3-isopropoxy-4-(2-methoxybenzyl)-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(3-isopropoxy-4-(3-methoxybenzyl)-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(3-isopropoxy-4-(4-methoxybenzyl)-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(2-fluorobenzyl)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(2-fluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(3-fluorobenzyl)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(3-fluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(4-fluorobenzyl)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-2-(4-(4-fluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-ethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
5-methoxy-2-[(4-phenoxyphenyl)amino]benzoic acid
-
-
5-methyl-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)pyrimidine
-
-
-
5-methyl-7-(naphthalen-2-yloxy)[1,2,4]triazolo[1,5-a]pyrimidine
5-methyl-7-(naphthalen-2-ylsulfanyl)[1,2,4]triazolo[1,5-a]pyrimidine
5-methyl-N-(2,3,4-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-(2,4,5-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-(3-methylphenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-(4-methylphenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-(4-nitrophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
5-methyl-N-[3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-[4-(trifluoromethoxy)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
5-methyl-N-[4-methyl-3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
6-chloro-2-(2'-fluorobiphenyl-4-yl)quinoline-4-carboxylic acid
-
-
-
6-methyl-N-phenyl-3aH-inden-4-amine
7-methyl-N-(naphthalen-2-yl)imidazo[1,2-a]pyrimidin-5-amine
-
-
7-methyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyridin-5-amine
-
-
benzoquinones
-
ubiquinone-0 and decylubiquinone
-
biphenyl-4-yl-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
cis-5-methyldihydroorotate
-
-
dichloroallyl lawsone
-
50% inhibition at 0.00051 mM, wild-type, 0.00031 mM, DELTA2-21 mutant, 0.00020 mM, DELTA22-37 mutant, 0.00021 mM, DELTA2-37 mutant
diethyl [(1H-benzimidazol-5-ylamino)methylidene]propanedioate
-
-
diethyl [(1H-indazol-5-ylamino)methylidene]propanedioate
-
-
diethyl [(5a,9a-dihydrodibenzo[b,d]thiophen-2-ylamino)methylidene]propanedioate
-
-
diethyl [(biphenyl-3-ylamino)methylidene]propanedioate
-
-
diethyl [(biphenyl-4-ylamino)methylidene]propanedioate
-
-
diethyl [(dibenzo[b,d]thiophen-2-ylamino)methylidene]propanedioate
diethyl {[(2-methylphenyl)amino]methylidene}propanedioate
-
-
diethyl {[(4-methylphenyl)amino]methylidene}propanedioate
-
-
ethyl (2Z)-3-(biphenyl-3-ylamino)-2-cyanoprop-2-enoate
-
-
ethyl (2Z)-3-(biphenyl-4-ylamino)-2-cyanoprop-2-enoate
-
-
ethyl 2-((2,3-dihydro-1h-inden-5-yl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3'-methoxy-[1,1'-biphenyl]-4-yl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3,4-dichlorophenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3,4-dimethylphenyl)amino)-4-methylthiazole-5-carboxylate
-
-
ethyl 2-((3,4-dimethylphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3,5-dichlorophenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3,5-difluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)-amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-chloro-4-((2-chloro-6-fluorobenzyl)oxy)phenyl)-amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-cyclopropylthiazole-5-carboxylate
-
-
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-methylthiazole-5-carboxylate
-
-
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-chloro-4-phenoxyphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-fluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-fluoro-4-methylphenyl)amino)-4-methylthiazole-5-carboxylate
-
-
ethyl 2-((3-fluoro-4-methylphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((3-fluoro-[1,1'-biphenyl]-4-yl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-(benzyloxy)-3-chlorophenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-(tert-butyl)phenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-bromo-2-methylphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-bromo-3-(trifluoromethyl)phenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-bromophenyl)amino)-4-methylthiazole-5-carboxylate
-
-
ethyl 2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-4-(cyclopropanecarboxamido)thiazole-5-carboxylate
-
-
ethyl 2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-chlorophenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-((4-methoxyphenyl)amino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-(anthracen-2-ylamino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-(benzo[d][1,3]dioxol-5-ylamino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-(naphthalen-2-ylamino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 2-([1,1'-biphenyl]-4-ylamino)-4-phenylthiazole-5-carboxylate
-
-
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
ethyl 4-(cyclopropanecarboxamido)-2-((3,4-dimethylphenyl)amino)thiazole-5-carboxylate
-
-
ethyl 4-(tert-butyl)-2-((3,4-dimethylphenyl)amino)thiazole-5-carboxylate
-
-
ethyl 4-(tert-butyl)-2-((3-chloro-4-methylphenyl)amino)-thiazole-5-carboxylate
-
-
ethyl 4-(tert-butyl)-2-((3-fluoro-4-methylphenyl)amino)-thiazole-5-carboxylate
-
-
ethyl 4-amino-2-((3,4-dimethylphenyl)amino)thiazole-5-carboxylate
-
-
ethyl 4-amino-2-((4-chloro-3-(trifluoromethyl)phenyl)-amino)thiazole-5-carboxylate
-
-
ethyl 4-benzamido-2-((3,4-dimethylphenyl)amino)thiazole-5-carboxylate
-
-
ethyl 4-benzamido-2-((4-chloro-3-(trifluoromethyl)phenyl)-amino)thiazole-5-carboxylate
-
-
ethyl 4-cyclopropyl-2-((3,4-dimethylphenyl)amino)thiazole-5-carboxylate
-
-
ethyl 4-cyclopropyl-2-((4-fluoro-3-methylphenyl)amino)-thiazole-5-carboxylate
-
-
ethyl 4-methyl-2-(naphthalen-2-ylamino)thiazole-5-carboxylate
-
-
ethyl 4-phenyl-2-((4-(trifluoromethyl)phenyl)amino)-thiazole-5-carboxylate
-
-
ethyl 4-phenyl-2-((5,6,7,8-tetrahydronaphthalen-2-yl)-amino)thiazole-5-carboxylate
-
-
ethyl 4-phenyl-2-(phenylamino)thiazole-5-carboxylate
-
-
H2O2
-
byproduct, tends to inactivate enzyme
HR325
-
structural analogue of A77 1726
-
N-(2,3-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(2,4-dichlorophenyl)-2-naphthamide
-
50% inhibition at 0.00005 mM, wild type, 0.00008 mM, mutant R265A, above 0.05, mutant H185A
N-(2,4-dichlorophenyl)naphthalene-2-carboxamide
N-(2-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(2-fluoro-4-methylphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(2-fluorophenyl)-2-naphthamide
-
50% inhibition at 0.00047 mM, wild type, 0.00030 mM, mutant R265A, 0.21, mutant H185A
N-(2-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(3,4-dichlorophenyl)-2-methyl-3-nitrobenzamide
-
50% inhibition at 0.00008 mM, wild type, 0.0028 mM, mutant R265A, 0.06, mutant H185A
N-(3,4-difluorophenyl)-2-methyl-3-nitrobenzamide
-
50% inhibition at 0.00026 mM, wild type, 0.00082 mM, mutant R265A, 0.25, mutant H185A
N-(3,4-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3,4-dimethylphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3,5-dichloro-phenyl)-2-methyl-3-nitro-benzamide
-
-
N-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide
N-(3,5-difluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3-bromophenyl)-2-methyl-3-nitrobenzamide
-
50% inhibition at 0.00006 mM, wild type, 0.0012 mM, mutant R265A, 0.140, mutant H185A
N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
-
N-(3-chloro-4-fluorophenyl)-2-methyl-3-nitrobenzamide
-
50% inhibition at 0.0001 mM, wild type, 0.0005 mM, mutant R265A, 0.13, mutant H185A
N-(3-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(3-fluoro-4-methylphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(4-benzylphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(4-bromo-2-methylphenyl)-2-naphthamide
-
50% inhibition at 0.00005 mM, wild type, 0.00005 mM, mutant R265A, 0.57, mutant H185A
N-(4-bromophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(4-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(4-fluoro-3-methylphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(4-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(4-methoxyphenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(anthracen-2-yl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(anthracen-2-yl)-N,5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-(biphenyl-4-yl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-anthracen-2-yl-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
i.e. DSM2
N-cyclopropyl-5-(2,3-dihydro-4H-1,4-benzothiazin-4-yl)thiophene-2-carboxamide
N-cyclopropyl-5-[4-(difluoromethoxy)-2-methyl-1H-benzimidazol-1-yl]thiophene-2-carboxamide
-
-
N-propyl-5-(1H-pyrazol-1-yl)thiophene-2-carboxamide
N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N-[4-(difluoromethoxy)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-[4-bromo-3-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-[4-chloro-3-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
rhodamine 123
-
mitochondrial inhibitor
[2-fluoro-2',5'-dimethyl-4'-[6-(3-methyl-2-butenyloxy)pyridin-3-yl]biphenyl-4-yl]-(3-methyl-2-butenyl)amine
(2Z)-2-cyano-3-cyclopropyl-3-hydroxy-N-[4-(trifluoromethyl)phenyl]prop-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-3-cyclopropyl-3-hydroxy-N-[4-(trifluoromethyl)phenyl]prop-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2',3-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2',3-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2,2'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2,2'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2,3'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(2,3'-dichlorobiphenyl-4-yl)-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(3'-ethoxybiphenyl-4-yl)-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-2-cyano-N-(3'-ethoxybiphenyl-4-yl)-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-(2'-chlorobiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-(2'-chlorobiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-(3-chloro-2'-methoxybiphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-(biphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
(2Z)-N-(biphenyl-4-yl)-2-cyano-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
(2Z)-N-[2'-chloro-3-(trifluoromethyl)biphenyl-4-yl]-2-cyano-3-hydroxybut-2-enamide

-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
(2Z)-N-[2'-chloro-3-(trifluoromethyl)biphenyl-4-yl]-2-cyano-3-hydroxybut-2-enamide
-
inhibitor based on the active metabolite of the anti-inflammatory drug leflunomide. Comparison of inhibitory effect and binding to human and Plasmodium falciparum enzyme
-
1-(2-methoxyphenyl)-3-naphthalen-1-ylurea

-
-
1-(2-methoxyphenyl)-3-naphthalen-1-ylurea
-
-
2-cyano-3-(9-ethyl-9H-carbazol-3-ylamino)acrylic acid ethyl ester

-
IC50: 0.491 mM
2-cyano-3-(9-ethyl-9H-carbazol-3-ylamino)acrylic acid ethyl ester
-
IC50: 0.00044 mM
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(cyano)phenyl]-propenamide

-
50% inhibition at 0.0.00035 mM, N-terminally truncated protein
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(cyano)phenyl]-propenamide
50% inhibition at 0.712 mM, N-terminally truncated protein
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(nitro)phenyl]-propenamide

-
50% inhibition at 0.00025 mM, N-terminally truncated protein
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(nitro)phenyl]-propenamide
50% inhibition at 0.543 mM, N-terminally truncated protein
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(trifluoromethyl)phenyl]-propenamide

-
50% inhibition at 0.00019 mM, N-terminally truncated protein
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(trifluoromethyl)phenyl]-propenamide
50% inhibition at 1.08 mM, N-terminally truncated protein
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide

-
anti-proliferative effect of A77 1726 is mediated by inhibition of enzyme
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
inbibits by interference with the transfer of electrons from flavin to quinone
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
A77 1726, active metabolite of leflumonide
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
noncompetitive versus ubiquinone, uncompetitive versus dihydroorotate, study of kinetics
2-[(2,5-dichlorophenyl)sulfanyl]-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol

-
compound has therapeutically relevant activity against human enzyme
2-[(2,5-dichlorophenyl)sulfanyl]-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
-
no specific inhibition of Plasmodium enzyme, good inhibitor of human enzyme
2-[(2,5-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol

-
compound has therapeutically relevant activity against human enzyme
2-[(2,5-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
-
no specific inhibition of Plasmodium enzyme, good inhibitor of human enzyme
2-[(3,4-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol

-
compound is less active with human enzyme but good inhibitor of Plasmodium falciparum enzyme
2-[(3,4-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
-
-
2-[(4-chlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol

-
compound is less active with human enzyme but good inhibitor of Plasmodium falciparum enzyme
2-[(4-chlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
-
-
2-[(E)-2-(2-methylphenyl)ethenyl]quinolin-4-ol

-
-
2-[(E)-2-(2-methylphenyl)ethenyl]quinolin-4-ol
-
-
3-hydroxy-2-(3,3-dichloroallyl)-1,4-naphthoquinone

-
50% inhibition at 0.000065 mM, i. e. dichloroallyl lawsone, N-terminally truncated protein
3-hydroxy-2-(3,3-dichloroallyl)-1,4-naphthoquinone
50% inhibition at 0.220 mM, i. e. dichloroallyl lawsone, N-terminally truncated protein
4-pentyl-1,3,4,10-tetrahydroacridin-9(2H)-one

-
-
4-pentyl-1,3,4,10-tetrahydroacridin-9(2H)-one
-
-
4-pentyl-1,3,4,10-tetrahydroacridin-9(2H)-one
-
-
4-pentyl-1,3,4,10-tetrahydroacridin-9(2H)-one
-
-
5,6-dimethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
5,6-dimethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-(1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(1H-indol-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(1H-indol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(2-methyl-1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(2-methyl-1H-benzimidazol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(2-methyl-1H-indol-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(2-methyl-1H-indol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(2-methyl-1H-indol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(2-methyl-1H-indol-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(4-methylpiperazin-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(4-methylpiperazin-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-(piperidin-1-yl)-N-propylthiophene-2-carboxamide

-
-
5-(piperidin-1-yl)-N-propylthiophene-2-carboxamide
-
-
5-ethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
5-ethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-7-(naphthalen-2-yloxy)[1,2,4]triazolo[1,5-a]pyrimidine

-
-
5-methyl-7-(naphthalen-2-yloxy)[1,2,4]triazolo[1,5-a]pyrimidine
-
-
5-methyl-7-(naphthalen-2-ylsulfanyl)[1,2,4]triazolo[1,5-a]pyrimidine

-
-
5-methyl-7-(naphthalen-2-ylsulfanyl)[1,2,4]triazolo[1,5-a]pyrimidine
-
-
5-methyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
5-methyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
i.e. DSM1
5-methyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
i.e. DSM74
5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
5-Methylorotate

-
-
6-methyl-N-phenyl-3aH-inden-4-amine

-
-
6-methyl-N-phenyl-3aH-inden-4-amine
-
-
A77 1726

-
active metabolite of leflunomide
A77 1726
-
malononitrilamide, 50% inhibition at 18-773 nM
A77 1726
-
active metabolite of the anti-rheumatic drug leflunomide
A77 1726
-
inhibits cell growth in multiple myeloma cell lines at clinically achievable concentrations by induction of apoptosis. Inhibition of cell growth is partly due to inhibition of multiple myeloma cell proliferation. A77 1726 shows synergistic and additive activity together with genotoxic agents melphalan, treosulfan, and doxorubicin
A77 1726
-
malononitrilamide, 50% inhibition at 18-773 nM
A77 1726
-
active metabolite of the anti-rheumatic drug leflunomide
A77 1726
-
malononitrilamide, 50% inhibition at 18-773 nM
A77-1726

-
50% inhibition at 0.00045 mM, wild-type, 0.00033 mM, DELTA2-21 mutant, 0.00031 mM, DELTA22-37 mutant, 0.00036 mM, DELTA2-37 mutant
A77-1726
-
potent inhibitor
atovaquone

-
competitive to quinone
atovaquone
-
competitive to quinone
atovaquone
-
50% inhibition at 0.000698 mM, wild-type enzyme, 0.000904 mM, DELTA1-29 mutant
Barbituric acid

-
-
Barbituric acid
-
competitive to dihydroorotate, dead-end inhibitor
brequinar

-
50% inhibition at 0.567 mM, wild-type, 0.528 mM, DELTA2-21 mutant, 0.615 mM, DELTA22-37 mutant, 0.662 mM, DELTA2-37 mutant
brequinar
-
sensitive to brequinar at a 0.01 mM concentration
brequinar
-
poor inhibitor
brequinar
-
50% inhibition at 0.000367 mM, wild-type enzyme, 0.000127 mM, DELTA1-29 mutant
brequinar sodium

-
complete activity termination in all tissues at 0.01 mM
brequinar sodium
1 mM reduces the activity by more than 50% of the full-length enzyme
brequinar sodium
-
complete activity termination in all tissues at 0.01 mM
brequinar sodium
-
tight binding, most potent inhibitor, mutant H26A is insensitive, wild-type and other mutants are inhibited by 50% at concentrations between 6 and 10 nM
brequinar sodium
-
potent, noncompetitive inhibitor
brequinar sodium
-
more active than A77 1726 and HR325
brequinar sodium
-
50% inhibition at 6-127 nM
brequinar sodium
-
complete activity termination in all tissues at 0.01 mM
brequinar sodium
-
; inbibits by interference with the transfer of electrons from flavin to quinone
brequinar sodium
-
competitive versus ubiquinone, uncompetitive versus dihydroorotate, study of kinetics
brequinar sodium
-
50% inhibition at 6-127 nM
brequinar sodium
-
complete activity termination in all tissues at 0.01 mM
brequinar sodium
-
50% inhibition at 6-127 nM
brequinar sodium
complete activity termination in all tissues at 0.01 mM
brequinar sodium
-
complete activity termination in all tissues at 0.01 mM
dichloroallyl-lawsone

-
competitive to quinone
dichloroallyl-lawsone
-
competitive to quinone
diethyl [(dibenzo[b,d]thiophen-2-ylamino)methylidene]propanedioate

-
-
diethyl [(dibenzo[b,d]thiophen-2-ylamino)methylidene]propanedioate
-
-
diethyldicarbonate

-
histidine-selective covalent modifier
diethyldicarbonate
-
histidine-selective covalent modifier; histidine-selective modifying agent, dose-dependent
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

-
-
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
-
-
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
-
-
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
-
-
fatty acids

-
-
fatty acids
-
noncompetitive with respect to ubiquinone
Genz-667348

-
-
Genz-668857

-
-
Genz-669178

-
-
Lapachol

-
-
Lawsone

-
-
leflunomide

-
-
leflunomide
-
poor inhibitor
MNA 279

-
malononitrilamide, 50% inhibition at 22-715 nM
MNA 279
-
malononitrilamide, 50% inhibition at 22-715 nM
MNA 279
-
malononitrilamide, 50% inhibition at 22-715 nM
MNA 715

-
malononitrilamide, 50% inhibition at 41-109 nM
MNA 715
-
malononitrilamide, 50% inhibition at 41-109 nM
MNA 715
-
malononitrilamide, 50% inhibition at 41-109 nM
N-(2,4-dichlorophenyl)naphthalene-2-carboxamide

-
-
N-(2,4-dichlorophenyl)naphthalene-2-carboxamide
-
-
N-(2-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(2-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(2-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(2-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide

-
-
N-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide
-
50% inhibition at 0.00002 mM, wild type, 0.0004 mM, mutant R265A, 0.13, mutant H185A
N-(3,5-dichlorophenyl)-2-methyl-3-nitrobenzamide
-
-
N-(3-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(3-chlorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(3-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(3-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(4-bromophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(4-bromophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(4-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(4-fluorophenyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(anthracen-2-yl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(anthracen-2-yl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-(anthracen-2-yl)-N,5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-(anthracen-2-yl)-N,5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
N-cyclopropyl-5-(2,3-dihydro-4H-1,4-benzothiazin-4-yl)thiophene-2-carboxamide

-
-
N-cyclopropyl-5-(2,3-dihydro-4H-1,4-benzothiazin-4-yl)thiophene-2-carboxamide
-
-
N-cyclopropyl-5-(2,3-dihydro-4H-1,4-benzothiazin-4-yl)thiophene-2-carboxamide
-
-
N-propyl-5-(1H-pyrazol-1-yl)thiophene-2-carboxamide

-
-
N-propyl-5-(1H-pyrazol-1-yl)thiophene-2-carboxamide
-
-
N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

-
-
N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
Orotate

-
competitive to dihydroorotate
Orotate
-
competitive to dihydroorotate
Orotate
-
also inhibitors: 5-substituted orotates; competitive to dihydroorotate; strong competitive inhibitor
redoxal

0.5 mM exhibit an inhibitory effect of more than 50% on full-length DHODH and N-terminally truncated DHODH compared with the noninhibited reaction
redoxal
-
50% inhibition at 0.029 mM, wild-type, 0.057 mM, DELTA2-21 mutant, 0.040 mM, DELTA22-37 mutant, 0.056 mM, DELTA2-37 mutant
redoxal
-
50% inhibition at 45-88 nM
redoxal
-
50% inhibition at 0.000013 mM, N-terminally truncated protein
redoxal
-
50% inhibition at 45-88 nM
redoxal
50% inhibition at 0.071 mM, N-terminally truncated protein
redoxal
-
50% inhibition at 45-88 nM
teriflunomide

-
a redox-silent coenzyme Q antagonist of DHODH
Thenoyltrifluoroacetone

-
-
Thenoyltrifluoroacetone
-
-
toltrazuril

-
50% inhibition at 0.1 mM
toltrazuril
-
50% inhibition at 0.1 mM
toltrazuril
-
50% inhibition at 0.1 mM
toltrazuril
-
50% inhibition at 0.1 mM
toltrazuril
50% inhibition at 0.1 mM
toltrazuril
-
50% inhibition at 0.1 mM
[2-fluoro-2',5'-dimethyl-4'-[6-(3-methyl-2-butenyloxy)pyridin-3-yl]biphenyl-4-yl]-(3-methyl-2-butenyl)amine

-
i.e. S-2678, suppresses immunoglobulin production in human peripheral blood mononuclear cells in vitro, with little or no inhibition of cell proliferation
[2-fluoro-2',5'-dimethyl-4'-[6-(3-methyl-2-butenyloxy)pyridin-3-yl]biphenyl-4-yl]-(3-methyl-2-butenyl)amine
-
i.e. S-2678, suppresses immunoglobulin production in mouse B cells in vitro, with little or no inhibition of cell proliferation, probably through inhibition of class switch recombination in the immunoglobulin heavy chain loci in B cells. In vivo antibody production induced by systemic immunization with ovalbumin is dramatically suppressed by oral administration of S-2678, without any toxicological signs. S-2678 does not affect T-cell activation in vitro, and cytokine production induced by intravenous anti-CD3 antibody in mice. S-2678 does not affect host defense in a mouse model of Candida infection, whereas leflunomide severely impaires it
additional information

-
kinetics of inhibition
-
additional information
-
competitive nature of small molecule inhibitors toward the putative ubiquinone binding site
-
additional information
-
DHODH-specific inhibitors with low nanomolar binding affinities bind in the N-terminal hydrophobic channel of dihydroorotate dehydrogenase, the presumed site of ubiquinone binding during oxidation of dihydroorotate to orotate
-
additional information
-
screening for potent inhibitors of PfDHODH and effect on the human enzyme, overview. The compiunds show strong selectivity for the malarial enzyme over that from the human host, inhibition mechanism, overview
-
additional information
-
drug screening and identification of a series of N-alkyl-5-(1H-benzimidazol-1-yl)thiophene-2-carboxamides with low nanomolar in vitro potency against DHODH, selective for the parasite enzymes over human DHODH, tolerability in the mouse, overview
-
additional information
-
DHODH-specific inhibitors with low nanomolar binding affinities bind in the N-terminal hydrophobic channel of dihydroorotate dehydrogenase, the presumed site of ubiquinone binding during oxidation of dihydroorotate to orotate
-
additional information
-
development and evaluation of triazolopyrimidine-based DHODH inhibitors, overview. Detailed quantitative structure-activity relationship study and molecular docking studies, the 2-methyltriazolopyrimidine ring interacts with some polar and some nonpolar amino acids whereas the substituted phenyl ring binds with a hydrophobic pocket of the enzyme formed by some nonpolar amino acid residues, overview
-
additional information
-
screening for potent inhibitors of PfDHODH that show strong selectivity for the malarial enzyme over that from the human host. Lead optimization of a triazolopyrimidine-based series, inhibition mechanism, overview
-
additional information
-
drug screening and identifictaion of a series of N-alkyl-5-(1H-benzimidazol-1-yl)thiophene-2-carboxamides with low nanomolarin vitro potency against DHODH, selective for the parasite enzymes over human DHODH, tolerability in the mouse, overview
-
additional information
-
identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice, overview
-
additional information
-
drug screening and identification of a series of N-alkyl-5-(1H-benzimidazol-1-yl)thiophene-2-carboxamides with low nanomolar in vitro potency against DHODH, selective for the parasite enzymes over human DHODH, tolerability in the mouse, overview
-
additional information
-
not: bathophenathroline, sulfonate, ethylendiaminetetraacetate, cyanide, azide
-
additional information
-
kinetics of inhibition
-
additional information
-
not inhibitory: brequinar, atovaquone, N-(3,5-difluoro-4-(trifluoromethyl)phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
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