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Enzyme Nomenclature
Information on EC 1.3.5.2 - dihydroorotate dehydrogenase (quinone)
for references in articles please use BRENDA:EC1.3.5.2
Word Map on EC 1.3.5.2
- 1.3.5.2
- pyrimidine
- plasmodium
- leflunomide
- falciparum
- brequinar
- uridine
-
immunosuppressive
- arthritis
- malaria
-
antimalarial
-
dhods
-
rheumatoid
-
phosphoribosyltransferase
- dihydroorotase
- atovaquone
- triazolopyrimidine
- teriflunomide
- ump
- medicine
- orotidine
-
flavoenzyme
- coq
- 5-fluoroorotate
- pharmacology
-
antirheumatic
-
isoxazole
-
transcarbamoylase
-
pyre
-
dmards
- decylubiquinone
-
species-selective
- drug development
- l-dihydroorotate
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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EC NUMBER 
COMMENTARY 
1.3.5.2
-
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RECOMMENDED NAME
GeneOntology No.
dihydroorotate dehydrogenase (quinone)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-dihydroorotate + a quinone = orotate + a quinol
different binding sites for dihydroorotate and the electron acceptor, two-site ping-pong mechanism. Cleavage site at R182 is conserved between the two major families of dihydroorotate dehydrogenases, it is positioned in a loop, which is crucial for catalysis but irrelevant for protein stability; ping-pong mechanism
-
(S)-dihydroorotate + a quinone = orotate + a quinol
one-site ping-pong mechanism, residues 129-137 form a flexible loop, responsible for substrate binding
-
(S)-dihydroorotate + a quinone = orotate + a quinol
existence of 3 families differing in their selectivity for oxidizing substrates: 1A are soluble, containing FMN and use fumarate, 1B are soluble, one subunit contains an iron-sulfur center, FAD and reduces NAD+, family 2 enzymes are membrane-bound, contain FMN and are oxidized by ubiquinone. Mechanism consists of 3 reaction phases. Different binding-mechanisms for enzyme the reaction-steps are suggested
-
(S)-dihydroorotate + a quinone = orotate + a quinol
fourth step in biosynthesis of pyrimidines. Two domains: alpha/beta-barrel domain containing the active site, one alpha-helical domain that forms the opening of a tunnel leading to active site
-
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
-
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
-
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
-
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
-
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
(S)-dihydroorotate + a quinone = orotate + a quinol
in liver, myocardium and skeletal muscle tissues the activity intensities vary from animal to animal, but are similar in ileum, colon and kidney cortex. Cardiac enzyme expresses a pronounced oxidase activity
-
(S)-dihydroorotate + a quinone = orotate + a quinol
68% identity with type A enzyme of Lactococcus lactis, two-site non-classical ping-pong kinetic mechanism
-
(S)-dihydroorotate + a quinone = orotate + a quinol
ping-pong mechanism; soluble quinones as second substrate
-
(S)-dihydroorotate + a quinone = orotate + a quinol
-
-
-
-
(S)-dihydroorotate + a quinone = orotate + a quinol
two-site ping-pong mechanism
(S)-dihydroorotate + a quinone = orotate + a quinol
enzyme uses a stepwise mechanism for dihydroorotate oxidation
(S)-dihydroorotate + a quinone = orotate + a quinol
the active base S175 and the hydrogen bonding network including residues T178 and F115 work together for efficient deprotonation of dihydroorotate
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(S)-dihydroorotate:quinone oxidoreductase
This Class 2 dihydroorotate dehydrogenase enzyme contains FMN [4]. The enzyme is found in eukaryotes in the mitochondrial membrane, in cyanobacteria, and in some Gram-negative and Gram-positive bacteria associated with the cytoplasmic membrane [2,5,6]. The reaction is the only redox reaction in the de-novo biosynthesis of pyrimidine nucleotides [2,4]. The best quinone electron acceptors for the enzyme from bovine liver are ubiquinone-6 and ubiquinone-7, although simple quinones, such as benzoquinone, can also act as acceptor at lower rates [2]. Methyl-, ethyl-, tert-butyl and benzyl (S)-dihydroorotates are also substrates, but methyl esters of (S)-1-methyl and (S)-3-methyl and (S)-1,3-dimethyldihydroorotates are not [2]. Class 1 dihydroorotate dehydrogenases use either fumarate (EC 1.3.98.1), NAD+ (EC 1.3.1.14) or NADP+ (EC 1.3.1.15) as electron acceptor.
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CAS REGISTRY NUMBER
COMMENTARY
59088-23-2
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
-
GenBank
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
-
Plasmodium DHODH is an essential mitochondrial enzyme that catalyzes the flavin mononucleotide-dependent formation of orotic acid, a key step in de novo pyrimidine biosynthesis
physiological function
-
dihydroorotate dehydrogenase is associated with mitochondrial electron transport and required for de novo pyrimidine synthesis, and is required for N-(4-hydroxyphenyl)retinamide-induced reactive oxygen species production and apoptosis. Chemical inhibition of DHODH activity or the reduction of DHODH protein suppresses 4HPR-induced ROS production and apoptosis in transformed skin and prostate epithelial cells, overview
physiological function
-
the enzyme is involved in de novo biosynthesis of pyrimidines
physiological function
-
the enzyme is involved in de novo biosynthesis of pyrimidines, which is essential in malaria. Absence of pyrimidine salvage pathways in Plasmodium, thus the de novo pathway provides the only source of pyrimidines for cell growth. The mitochondrial enzyme requires oxidized ubiquinone, thus coupling pyrimidine biosynthesis to the respiratory chain
physiological function
-
DHODH catalyzes the rate-limiting step in the pyrimidine biosynthetic pathway
physiological function
-
DHODH catalyzes the rate-limiting step in the pyrimidine biosynthetic pathway
physiological function
-
DHODH catalyzes the rate-limiting step in the pyrimidine biosynthetic pathway
physiological function
-
the gene appears to be essential, because while gene tagging is successful at the TgDHOD gene locus, attempts to delete the TgDHOD gene were not successful in the KU80 background
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(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 + decylubiquinone
orotate + decylubiquinol
-
-
-
-
?
(S)-dihydroorotate + decylubiquinone
orotate + reduced decylubiquinone
Q02172;
-
-
-
?
(S)-dihydroorotate + oxidized 2,6-dichloroindophenol
orotate + reduced 2,6-dichloroindophenol
-
-
-
-
?
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 + 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 + 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
-
-
?
L-dihydroorotate + 2,6-dichlorophenolindophenol
orotate + reduced 2,6-dichlorophenolindophenol
L-dihydroorotate + ubiquinone-0
orotate + reduced ubiquinone-0
-
-
-
?
L-dihydroorotate + ubiquinone-4
orotate + reduced ubiquinone-4
-
-
-
?
L-dihydroorotate + vitamin K3
orotate + reduced vitamin K3
-
-
-
?
methyl-dihydroorotate + acceptor
methyl-orotate + reduced acceptor
-
-
-
-
?
tert-butyl-dihydroorotate + acceptor
tert-butyl-orotate + reduced acceptor
-
-
-
-
?
(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
-
reaction studied with menadione, O2 and ferricyanide
-
?
(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
-
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
-
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
-
?
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: coenzyme Q6
-
-
?
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
-
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
-
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
-
acceptor: quinones
-
-
-
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 + 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
-
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
-
-
-
?
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
?
-
-
enzyme has methylviologen-fumarate reductase activity
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-dihydroorotate + acceptor
orotate + reduced acceptor
-
reduction of a number of substrates: fumatate, coenzyme ubiquinone-0 and menadione
-
?
(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
-
fourth step in synthesis of pyrimidine nucleotides
-
?
(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
-
fourth enzyme in pyrimidine synthesis
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth step in synthesis of uridine 5'-monophosphate
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
fourth enzyme in pyrimidine synthesis
-
?
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
Q63707
fourth enzyme in pyrimidine synthesis
-
ir
(S)-dihydroorotate + ubiquinone
orotate + ubiquinol
-
six-step biosynthesis of pyrimidine uridine monophosphate
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
physiological electron acceptor: ubiquinone (aerobic conditions), menaquinone (anaerobic conditions)
-
-
?
dihydroorotate + acceptor
orotate + reduced acceptor
-
fourth step in pyrimidine biosynthesis
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-methyl-1,4-naphthoquinone
little catalytic efficiency, N-terminally truncated protein
ubiquinone
-
the mitochondrial enzyme requires oxidized ubiquinone, CoQ
ubiquinone-0
little catalytic efficiency, N-terminally truncated protein
FMN
-
Lys100 and Lys225 enhance the structural stability of the active site by hydrogen bonding to the FMN cofactor
additional information
-
enzyme does not contain FAD, FMN, covalently bound flavin or ubiquinone
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Iron
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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
-
-
(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)-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
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-((4-bromo-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
1-(2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
-
-
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-(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-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-(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-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-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-hydroxyethylidene-cyano acetic acid 4-trifluoromethyl anilide
-
A177-1726, active derivative of human inhibitor leflunomide
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-[(biphenyl-4-ylamino)carbonyl]cyclopent-1-ene-1-carboxylic acid
-
50% inhibition at 0.00041 mM
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
-
-
-
4-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamino)-2-trifluoromethylbenzonitrile
-
-
4-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-(trifluoromethyl)benzonitrile
-
-
5-(4-cyano-2-methyl-1H-benzimidazol-1-yl)-N-cyclopropylthiophene-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-methyl-2-(4-(2,6-difluorophenoxy)-3-isopropoxy-5-methyl-1H-pyrazol-1-yl)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-(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-methyl-3-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
biphenyl-4-yl-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-amine
-
-
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 [(5a,9a-dihydrodibenzo[b,d]thiophen-2-ylamino)methylidene]propanedioate
-
-
ethyl 2-((3'-methoxy-[1,1'-biphenyl]-4-yl)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-fluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)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-bromo-3-(trifluoromethyl)phenyl)amino)-4-phenylthiazole-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 4-(cyclopropanecarboxamido)-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-((4-chloro-3-(trifluoromethyl)phenyl)-amino)thiazole-5-carboxylate
-
-
ethyl 4-benzamido-2-((4-chloro-3-(trifluoromethyl)phenyl)-amino)thiazole-5-carboxylate
-
-
ethyl 4-cyclopropyl-2-((4-fluoro-3-methylphenyl)amino)-thiazole-5-carboxylate
-
-
ethyl 4-phenyl-2-((5,6,7,8-tetrahydronaphthalen-2-yl)-amino)thiazole-5-carboxylate
-
-
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-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-(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-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-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-fluoro-4-methylphenyl)-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-fluoro-3-methylphenyl)-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
-
i.e. DSM2
N-cyclopropyl-5-[4-(difluoromethoxy)-2-methyl-1H-benzimidazol-1-yl]thiophene-2-carboxamide
-
-
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
-
-
[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
-
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
-
-
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
5,6-dimethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
-
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
-
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
-
-
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
-
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
atovaquone
-
50% inhibition at 0.000698 mM, wild-type enzyme, 0.000904 mM, DELTA1-29 mutant
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
-
50% inhibition at 0.000367 mM, wild-type enzyme, 0.000127 mM, DELTA1-29 mutant
brequinar sodium
1 mM reduces the activity by more than 50% of the full-length enzyme
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
-
; 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
complete activity termination in all tissues at 0.01 mM
diethyldicarbonate
-
histidine-selective covalent modifier; histidine-selective modifying agent, dose-dependent
ethyl 4-(4-ethoxybenzyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
-
-
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-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-(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-(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-[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
-
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 0.071 mM, N-terminally truncated protein
[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
-
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
-
not inhibitory: brequinar, atovaquone, N-(3,5-difluoro-4-(trifluoromethyl)phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
activity of the bc1 complex is essential for providing oxidized ubiqinone to DHODH for the formation of pyrimidines
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.035
ubiquinone-4
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
additional information
additional information
-
relative Km-values for wild-type and mutants listed for (S)-dihydroorotate and ubiquinone-6
-
0.076
(S)-dihydroorotate
-
wild type enzyme, at pH 8.0 and 25°C; wild-type, pH 8.0, 22°C
0.265
(S)-dihydroorotate
-
mutant enzyme N302S, at pH 8.0 and 25°C; mutant N302S, pH 8.0, 22°C
16
coenzyme Q1
-
mutant F227A, pH 8.0, 25°C; mutant Y528A, pH 8.0, 25°C
20
coenzyme QD
-
mutant F188A, pH 8.0, 25°C; mutant F227A, pH 8.0, 25°C
0.015
decylubiquinone
-
mutant enzyme N302S, at pH 8.0 and 25°C; mutant N302S, pH 8.0, 22°C
0.032
decylubiquinone
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
0.037
decylubiquinone
-
wild type enzyme, at pH 8.0 and 25°C; wild-type, pH 8.0, 22°C
0.04
dihydroorotate
N-terminally truncated DHODH, fixed concentration of dihydroorotate and varied concentrations of 2,6-dichloroindophenol from 0-0.2 mM
0.042
dihydroorotate
full-length DHODH, fixed concentration of dihydroorotate of 1.0 mM and varied concentrations of decylubiquinone from 0-0.2 mM
0.065
dihydroorotate
N-terminally truncated DHODH, fixed concentration of dihydroorotate of 1.0 mM and varied concentrations of decylubiquinone from 0-0.2 mM
0.108
dihydroorotate
full-length DHODH, concentration of dihydroorotate varied from 0-1.0 mM at fixed concentrations of 0.1 mM decylubiquinone and 0.06 mM 2,6-dichloroindophenol
0.111
dihydroorotate
N-terminally truncated DHODH, concentration of dihydroorotate varied from 0-1.0 mM at fixed concentrations of 0.1 mM decylubiquinone and 0.06 mM 2,6-dichloroindophenol
0.122
dihydroorotate
full-length DHODH, fixed concentration of dihydroorotate of 1.0 mM and varied concentrations of 2,6-dichloroindophenol from 0-0.2 mM
0.015
L-dihydroorotate
pH 8.0, 25°C, cosubstrate Q6, N-terminally truncated protein
0.016
L-dihydroorotate
pH 8.0, 25°C, cosubstrate QD, N-terminally truncated protein
0.021
L-dihydroorotate
pH 8.0, 25°C, cosubstrate Q4, N-terminally truncated protein
0.056
L-dihydroorotate
pH 8.0, 25°C, cosubstrate vitamin K3, N-terminally truncated protein
0.114
L-dihydroorotate
pH 8.0, 25°C, cosubstrate Q0, N-terminally truncated protein
0.062
ubiquinone-6
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1.8
ubiquinone-4
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
2
ubiquinone-6
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
additional information
additional information
-
relative turnover numbers for wild-type and mutants listed for (S)-dihydroorotate and ubiquinone6
-
38
(S)-dihydroorotate
-
mutant enzyme N302S, at pH 8.0 and 25°C; mutant N302S, pH 8.0, 22°C
86
(S)-dihydroorotate
-
wild type enzyme, at pH 8.0 and 25°C; wild-type, pH 8.0, 22°C
2.6
coenzyme Q1
-
mutant F188A, pH 8.0, 25°C; mutant F227A, pH 8.0, 25°C
5.1
coenzyme Q1
-
mutant L531A, pH 8.0, 25°C; mutant Y528W, pH 8.0, 25°C
1.8
decylubiquinone
pH 8.0, 25°C, cosubstrate L-dihydroorotate, N-terminally truncated protein
1.8
L-dihydroorotate
pH 8.0, 25°C, cosubstrate Q0, N-terminally truncated protein
2
L-dihydroorotate
pH 8.0, 25°C, cosubstrate Q4, N-terminally truncated protein; pH 8.0, 25°C, cosubstrate Q6, N-terminally truncated protein; pH 8.0, 25°C, cosubstrate QD, N-terminally truncated protein; pH 8.0, 25°C, cosubstrate vitamin K3, N-terminally truncated protein
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1100
(S)-dihydroorotate
-
wild type enzyme, at pH 8.0 and 25°C; wild-type, pH 8.0, 22°C
2300
decylubiquinone
-
wild type enzyme, at pH 8.0 and 25°C; wild-type, pH 8.0, 22°C
2500
decylubiquinone
-
mutant enzyme N302S, at pH 8.0 and 25°C; mutant N302S, pH 8.0, 22°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.4
2-cyano-3-cyclopropyl-3-hydroxy-N-[4'-(nitro)phenyl]-propenamide
pH 8.0, 25°C, varied substrate QD, N-terminally truncated protein
0.00005
2-cyano-3-(9-ethyl-9H-carbazol-3-ylamino)acrylic acid ethyl ester
-
-
0.0002 - 0.0009
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
competitive to dihydroorotate
0.0002 - 0.0009
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
competitive to ubiquinone, non-competitive to dihydroorotate, parent compound leflunomide has no inhibitory effect at concentrations up to 0.001 mM
0.001
2-hydroxyethylidene-cyanoacetic acid 4-trifluoromethyl anilide
-
non-competitive to decyclubiquinone
0.16
3-hydroxy-2-(3,3-dichloroallyl)-1,4-naphthoquinone
pH 8.0, 25°C, varied substrate L-dihydroorotate, N-terminally truncated protein
0.25
3-hydroxy-2-(3,3-dichloroallyl)-1,4-naphthoquinone
pH 8.0, 25°C, varied substrate QD, N-terminally truncated protein
0.059
redoxal
pH 8.0, 25°C, varied substrate L-dihydroorotate, N-terminally truncated protein
0.086
redoxal
pH 8.0, 25°C, varied substrate QD, N-terminally truncated protein
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000117 - 0.0925
(2Z)-2-cyano-3-cyclopropyl-3-hydroxy-N-[4-(trifluoromethyl)phenyl]prop-2-enamide
-
0.00017 - 0.0062
(2Z)-N-[2'-chloro-3-(trifluoromethyl)biphenyl-4-yl]-2-cyano-3-hydroxybut-2-enamide
-
0.00385
1-(2-((3,4-dimethylphenyl)amino)-4-methylthiazol-5-yl)-ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.00394
1-(2-((3-chloro-4-methylphenyl)amino)-4-methylthiazol-5-yl)ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
1-(2-((3-fluoro-4-methylphenyl)amino)-4-methylthiazol-5-yl)ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.00365
1-(2-((4-(tert-butyl)phenyl)amino)-4-methylthiazol-5-yl)-ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.00193
1-(2-((4-bromo-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
1-(2-((4-bromophenyl)amino)-4-methylthiazol-5-yl)-ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.00235
1-(2-((4-chloro-3-(trifluoromethyl)phenyl)amino)-4-methylthiazol-5-yl)ethanone
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
1-(2-(anthracen-2-ylamino)-4-methylthiazol-5-yl)ethan-1-one
Homo sapiens;
-
at pH 8.0 and 22°C
0.000562
1-(4-methyl-2-(naphthalen-2-ylamino)thiazol-5-yl)ethan-1-one
Homo sapiens;
-
at pH 8.0 and 22°C
0.000077
2,8-dimethyl-N-[4-(trifluoromethyl)phenyl]pyrrolo[1,2-a]pyrimidin-4-amine
Plasmodium falciparum;
-
pH and temperature not specified in the publication
0.096
2-cyano-3-hydroxy-N-(2',3,3'-trichlorobiphenyl-4-yl)but-2-enamide
Toxoplasma gondii;
-
pH 8.0, 30°C
0.091
2-hydroxyethylidene-cyano acetic acid 4-trifluoromethyl anilide
Toxoplasma gondii;
-
pH 8.0, 30°C
0.000013 - 0.1
2-[(2,5-dichlorophenyl)sulfanyl]-5-ethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
0.000051 - 0.011
2-[(2,5-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
0.0019 - 0.0065
2-[(3,4-dichlorophenyl)sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol
0.001
2-[[(4-chlorophenyl)methyl]sulfanyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one
Plasmodium falciparum;
-
pH and temperature not specified in the publication
0.00016
5,6-dimethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
Plasmodium falciparum;
-
pH not specified in the publication, temperature not specified in the publication
0.00019
5-ethyl-N-(naphthalen-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
Plasmodium falciparum;
-
pH not specified in the publication, temperature not specified in the publication
0.0017
5-methyl-7-(naphthalen-2-yloxy)[1,2,4]triazolo[1,5-a]pyrimidine
Plasmodium falciparum;
-
pH not specified in the publication, temperature not specified in the publication
0.1
5-methyl-7-(naphthalen-2-ylsulfanyl)[1,2,4]triazolo[1,5-a]pyrimidine
Plasmodium falciparum;
-
above, pH not specified in the publication, temperature not specified in the publication
0.00028 - 0.025
5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine
0.000015
6-chloro-2-(2'-fluorobiphenyl-4-yl)quinoline-4-carboxylic acid
Homo sapiens;
-
pH 8.0, 22°C
-
0.1
6-methyl-N-phenyl-3aH-inden-4-amine
Plasmodium falciparum;
-
above, pH not specified in the publication, temperature not specified in the publication
0.000026
ethyl 2-((2,3-dihydro-1h-inden-5-yl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
ethyl 2-((3'-methoxy-[1,1'-biphenyl]-4-yl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000174
ethyl 2-((3,4-dichlorophenyl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.001358
ethyl 2-((3,4-dimethylphenyl)amino)-4-methylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000058
ethyl 2-((3,4-dimethylphenyl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000393
ethyl 2-((3,5-dichlorophenyl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000311
ethyl 2-((3,5-difluoro-3'-methoxy-[1,1'-biphenyl]-4-yl)-amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
ethyl 2-((3-chloro-4-((2-chloro-6-fluorobenzyl)oxy)phenyl)-amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000372
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-cyclopropylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000969
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-methylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.000035
ethyl 2-((3-chloro-4-methylphenyl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C
0.01
ethyl 2-((3-chloro-4-phenoxyphenyl)amino)-4-phenylthiazole-5-carboxylate
Homo sapiens;
-
at pH 8.0 and 22°C