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10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
6-hydroxymethylpterin + NADPH
6-hydroxymethyl-7,8-dihydropterin + NADP+
-
-
-
-
?
6-methylpterin + NADPH
6-methyl-7,8-dihydropterin + NADP+
-
-
-
-
?
7,8-dihydrofolate + acetylpyridine adenine nucleotide, reduced
5,6,7,8-tetrahydrofolate + acetylpyridine adenine nucleotide, oxidized
-
-
-
?
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
7,8-dihydrofolate + NADP + H+
5,6,7,8-tetrahydrofolate + NADP+
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
8-methylpterin + NADPH
8-methyl-7,8-dihydropterin + NADP+
D-erythro-7,8-neopterin + NADPH
?
-
low activity
-
-
?
D-threo-neopterin + NADPH
?
-
low activity
-
-
?
dihydrobiopterin + NADPH
? + NADP+
-
10% of the activity with 7,8-dihydrofolate
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
dihydropteroate + NADPH
?
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
L-erythro-neopterin + NADPH
?
-
-
-
-
?
L-threo-7,8-dihydroneopterin + NADPH
?
-
low activity
-
-
?
L-threo-neopterin + NADPH
?
-
-
-
-
?
pterin + NADPH
7,8-dihydropterin + NADP+
-
low activity
-
-
?
xanthopterin + NADPH
?
-
low activity
-
-
?
additional information
?
-
10-formyl-dihydrofolate + NADPH + H+

10-formyl-tetrahydrofolate + NADP+
-
-
-
?
10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
-
-
-
?
10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADH + H+

5,6,7,8-tetrahydrofolate + NAD+
-
-
-
-
r
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
-
-
-
-
r
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
-
-
-
-
?
7,8-dihydrofolate + NADP + H+

5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADP + H+
5,6,7,8-tetrahydrofolate + NADP+
-
assay at 37ưC
-
-
?
7,8-dihydrofolate + NADPH

5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?, r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
directly correlated with thymidylate synthesis
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
key enzyme in biosynthesis of purines, pyrimidines and several amino acids
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
enzyme plays important role in nucleotide biosynthesis
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
reverse reaction at only one tenth of forward reaction
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
clear evidence against dihydrofolate substrate channeling in the bifunctional thymidylate synthase-dihydrofolate reductase
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
strongly specific for
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?, r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
kinetic mechanism
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
cannot use NADH as reducing agent
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
water can serve as the Bronsted acid for the protonation of N5 of dihydrofolate during DHFR catalyzed reduction
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
strongly specific for
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
enzyme content of methotrexate-insensitive cell line VA2-B is 200fold higher than that of sensitive cell line HeLa BU-25 due to production of alternate enzyme type
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
key role in thymidylate biosynthesis
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
bifunctional enzyme DHFR-thymidylate synthase
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
?, r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
Pigeon
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
Pigeon
-
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
DHFR activity is not essential for virus replication
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
protozoa
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
protozoa
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
ir
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
at neutral pH the forward reaction is favored
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium strongly favors tetrahydrofolate production
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
equilibrium constant: 320000000000
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
at pH 7 hydride transfer is at least partially rate limiting for temperatures below 50ưC, at higher temperatures hydride transfer is faster than the steady state
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+

5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
DHFR catalyzes hydride transfer from the cofactor NADPH to 7,8-dihydrofolate to produce tetrahydrofolate requiring electrostatic complementarity between the enzyme and the transition state
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
the reaction is essential in DNA synthesis
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
the conserved residues Leu28, Val31, Ile50 and Leu54 forming a hydrophobic pocket in the enzyme are the binding site for the p-aminobenzamide moiety of the substrate dihydrofolate
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
8-methylpterin + NADPH

8-methyl-7,8-dihydropterin + NADP+
-
-
subsequently reduced more slowly and incompletely to 8-methyl-5,6,7,8-tetrahydropterin
?
8-methylpterin + NADPH
8-methyl-7,8-dihydropterin + NADP+
-
-
subsequently reduced more slowly and incompletely to 8-methyl-5,6,7,8-tetrahydropterin
?
8-methylpterin + NADPH
8-methyl-7,8-dihydropterin + NADP+
-
-
subsequently reduced more slowly and incompletely to 8-methyl-5,6,7,8-tetrahydropterin
?
dihydrofolate + NADPH + H+

tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
r
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH

5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
slow rate
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
bifunctional enzyme DHFR-thymidylate synthase
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
at a slow rate, reaction not catalyzed by all dihydrofolate reductases
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
slow rate
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
no activity
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
slow rate
-
?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
activity only at acidic pH around 4.5
-
?
additional information

?
-
a bifunctional enzyme with dihydrofolate reductase and thymidylate synthase activities, overview
-
-
?
additional information
?
-
-
a bifunctional enzyme with dihydrofolate reductase and thymidylate synthase activities, overview
-
-
?
additional information
?
-
-
equilibrium strongly favors tetrahydrofolate production
-
-
?
additional information
?
-
-
key enzyme in the biosynthesis of purines, pyrimidines and several amino acids
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
key enzyme in the biosynthesis of purines, pyrimidines and several amino acids
-
-
?
additional information
?
-
-
equilibrium strongly favors tetrahydrofolate production
-
-
?
additional information
?
-
-
no activity with 7,8-dihydrobiopterin and biopterin
-
-
?
additional information
?
-
-
no activity with folate, sepiapterin, isoxanthopterin, leucopterin
-
-
?
additional information
?
-
-
in Cryptosporidium, DHFR and thymidylate synthase are present as a bifunctional enzyme, DHFR-TS
-
-
?
additional information
?
-
-
-
-
-
?
additional information
?
-
-
3-acetylpyridine adenine dinucleotide + dihydrofolate: rapid equilibrium random mechanism
-
-
?
additional information
?
-
-
NADPH + dihydrofolate: steady-state random mechanism
-
-
?
additional information
?
-
enzyme activity decreases with increasing pressure. The Km values for dihydrofolate and NADPH are slightly higher at 200 MPa than at atmospheric pressure. The hydride transfer step is insensitive to pressure, while the dissociation constants of substrates and cofactors increase with pressure
-
-
?
additional information
?
-
-
enzyme activity decreases with increasing pressure. The Km values for dihydrofolate and NADPH are slightly higher at 200 MPa than at atmospheric pressure. The hydride transfer step is insensitive to pressure, while the dissociation constants of substrates and cofactors increase with pressure
-
-
?
additional information
?
-
free energy perturbation with molecular dynamics simulations of dihydrofolate reductase in complex with dihydrofolate. In the Michaelis complex the pKa is modulated by the Met20 loop fluctuations, providing the largest pKa shift in substates with a tightly closed loop conformation, in the partially closed/open substates, the pKa is similar to that in the occluded complex. Conducive to the protonation, tightly closing the Met20 loop enhances the interactions of the cofactor and the substrate with the Met20 side chain and aligns the nicotinamide ring of the cofactor coplanar with the pterin ring of the substrate
-
-
?
additional information
?
-
-
free energy perturbation with molecular dynamics simulations of dihydrofolate reductase in complex with dihydrofolate. In the Michaelis complex the pKa is modulated by the Met20 loop fluctuations, providing the largest pKa shift in substates with a tightly closed loop conformation, in the partially closed/open substates, the pKa is similar to that in the occluded complex. Conducive to the protonation, tightly closing the Met20 loop enhances the interactions of the cofactor and the substrate with the Met20 side chain and aligns the nicotinamide ring of the cofactor coplanar with the pterin ring of the substrate
-
-
?
additional information
?
-
-
equilibrium strongly favors tetrahydrofolate production
-
-
?
additional information
?
-
both dihydrolfolate reductase and thymidylate synthase are substrates for UBC9-catalyzed modification with small ubiquitin-like modifier-1
-
-
?
additional information
?
-
-
dihydrofolate reductase is a substrate of ubiquitin ligase MDM2. MDM2 binds directly to dihydrofolate reductase and catalyzes its monoubiquitination. It reduces dihydrofolate reductase activity in a p53-independent manner, but has no effect on the steady-state level of expression. the ability of MDM2 to inhibit dihydrofolate reductase deoends on an active MDM2 RING-finger domain
-
-
?
additional information
?
-
-
no activity with pterins
-
-
?
additional information
?
-
-
dihydrofolate reductase deficient mutant needs thymidine for growth, pathway overview
-
-
?
additional information
?
-
-
knockout mutants with either no pteridine reductase or dihydrofolate reductase activity revealed in comparison to wild-type that 90% of the cellular dihydrofolate reduction activity belongs to DHFR and 10% of the cellular dihydrofolate reductase activity belongs to pteridine reductase
-
-
?
additional information
?
-
-
assay method development
-
-
?
additional information
?
-
substrate binding site analysis, overview
-
-
?
additional information
?
-
-
substrate binding site analysis, overview
-
-
?
additional information
?
-
-
no activity with 7,8-dihydrobiopterin and biopterin
-
-
?
additional information
?
-
-
equilibrium strongly favors tetrahydrofolate production
-
-
?
additional information
?
-
molecular mechanism of the distinct differences in substrate channeling behavior between Toxoplasma gondii TS-DHFR and Cryptosporidium hominis TS-DHFR, overview
-
-
?
additional information
?
-
-
molecular mechanism of the distinct differences in substrate channeling behavior between Toxoplasma gondii TS-DHFR and Cryptosporidium hominis TS-DHFR, overview
-
-
?
additional information
?
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
additional information
?
-
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
additional information
?
-
no activity with folic acid and the structurally related pterins (biopterin, dihydrobiopterin, sepiapterin and neopterin) as substrates by enzyme DHFR-TS
-
-
?
additional information
?
-
-
no activity with folic acid and the structurally related pterins (biopterin, dihydrobiopterin, sepiapterin and neopterin) as substrates by enzyme DHFR-TS
-
-
?
additional information
?
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
additional information
?
-
no activity with folic acid and the structurally related pterins (biopterin, dihydrobiopterin, sepiapterin and neopterin) as substrates by enzyme DHFR-TS
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
additional information
?
-
10-formyl-dihydrofolate + NADPH + H+

10-formyl-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
10-formyl-dihydrofolate + NADPH + H+
10-formyl-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADPH

5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
directly correlated with thymidylate synthesis
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
key enzyme in biosynthesis of purines, pyrimidines and several amino acids
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
key role in thymidylate biosynthesis
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
DHFR activity is not essential for virus replication
-
-
?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
-
maintainance of adequate levels of fully reduced folate in metabolism of proliferating cells
-
-
?
7,8-dihydrofolate + NADPH + H+

5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
the enzyme is involved in the folate recycling pathway
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
the reaction is essential in DNA synthesis
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
r
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
-
?
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
-
-
-
?
additional information

?
-
-
key enzyme in the biosynthesis of purines, pyrimidines and several amino acids
-
-
?
additional information
?
-
-
key enzyme in the biosynthesis of purines, pyrimidines and several amino acids
-
-
?
additional information
?
-
-
in Cryptosporidium, DHFR and thymidylate synthase are present as a bifunctional enzyme, DHFR-TS
-
-
?
additional information
?
-
-
dihydrofolate reductase deficient mutant needs thymidine for growth, pathway overview
-
-
?
additional information
?
-
-
knockout mutants with either no pteridine reductase or dihydrofolate reductase activity revealed in comparison to wild-type that 90% of the cellular dihydrofolate reduction activity belongs to DHFR and 10% of the cellular dihydrofolate reductase activity belongs to pteridine reductase
-
-
?
additional information
?
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
additional information
?
-
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
additional information
?
-
the bifunctional folate and pyrimidine-metabolising enzyme dihydrofolate reductase-thymidylate synthase dihydrofolate reductase-thymidylate synthase is expressed from a single gene as a homodimer comprising of an N-terminal DHFR domain fused via a linker peptide to a thymidylate synthase domain at the C-terminus
-
-
?
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(-)-epicatechin gallate
-
competitive to 7,8-dihydrofolate, formation of a slow dissociation ternary complex by the reaction of NADPH with the enzyme-inhibitor complex. Ionization state of E30 is critical for inhibitory activity
(-)-epigallocatechin gallate
-
competitive to 7,8-dihydrofolate, formation of a slow dissociation ternary complex by the reaction of NADPH with the enzyme-inhibitor complex. Ionization state of E30 is critical for inhibitory activity
(1E)-1-[4-[(3,5-dichloropyridin-4-yl)oxy]phenyl]ethanone thiosemicarbazone
-
-
(2,4-diaminopyrimidin-5-yl)methyl naphthalene-2-sulfonate
(2,5-dimethyl-1,4-phenylene)bis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
50% inhibition at 0.000075 mM
(2E)-1-(1-cyclohexylphthalazin-2(1H)-yl)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenoxyphthalazin-2(1H)-yl)prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(2-methylphenyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(3,3,3-trifluoropropyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(3,5-dimethylphenyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(3-fluorophenyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(3-methylbut-2-en-1-yl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(3-methylbutyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(4-fluorophenyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(4-methoxyphenoxy)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(4-methylphenoxy)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(4-methylphenyl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(hexan-3-yl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-(propan-2-yl)phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-[1-[4-(trifluoromethoxy)phenoxy]phthalazin-2(1H)-yl]prop-2-en-1-one
-
(2S)-2-((4-[(2-amino-6-ethyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)thio]benzoyl)amino)pentanedioic acid
50% inhibition at 0.00042 mM, additionally inhibitory on thymidylate synthase
(2S)-2-((4-[(2-amino-6-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)thio]benzoyl)amino)pentanedioic acid
50% inhibition at 0.0021 mM, additionally inhibitory on thymidylate synthase
(2S)-2-[(4-([(2,4-diaminopteridin-6-yl)methyl](methyl)amino)phenyl)formamido]pentanedioic acid
i.e, methotrexate, A DHFR inhibitor, binds at the DHFR active site
(2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid
-
in low-folate medium, up to 300-fold increase of inhibitory activity
(4-(1-[(5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(methyl)amino]ethyl)phenyl)methanol
(E)-5-[2-(2-methoxyphenyl)prop-1-en-1-yl]furo[2,3-d]pyrimidine-2,4-diamine
(Z)-5-[2-(2-methoxyphenyl)prop-1-en-1-yl]furo[2,3-d]pyrimidine-2,4-diamine
1,1'-{6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}bis(4-benzylpyrazinediium)
-
minimal inhibitory concentration: 0.003536 mM
1,1'-{6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}bis(4-methylpyrazinediium)
-
minimal inhibitory concentration: 0.002418 mM
1,1'-{6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}bis(4-phenylpyrazinediium)
-
minimal inhibitory concentration: 0.018 mM
1,3-phenylenebis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
50% inhibition at 0.000075 mM
1,4-bis-([N-(1-imino-1-guanidino-methyl)]sulfanylmethyl)-3,6-dimethyl-benzene
binding of the inhibitor has both a favorable entropy and enthalpy of binding. Positive binding cooperativity between inhibitor and the cofactor NADPH. Binding of inhibitor to DHFR is 285fold tighter in the presence of the NADPH cofactor than in its absence
1,4-phenylenebis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
-
1,6-bis-(4-fluoro-phenyl)-[1,3,5]triazine-2,4-diamine
-
IC50: 0.011 nM, 0.03 mM 7,8-dihydrofolate
1-(3-([(2,4-diaminopteridin-6-yl)methyl]amino)phenyl)ethanol
1-(3-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
1-(4-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
1-(4-nitrophenyl)-3-[4-[4-[(4-nitrophenyl)carbamoylamino]phenoxy]phenyl]urea
NSC80735, complete inhibition at 1 mM
1-([N-(1-imino-guanidino-methyl)]sulfanylmethyl)-3-trifluoromethyl-benzene
binding of the inhibitor has both a favorable entropy and enthalpy of binding. Positive binding cooperativity between inhibitor and the cofactor NADPH. Binding of inhibitor to DHFR in the absence of NADPH is not observed
1-N,4-N-bis(4-aminophenyl)benzene-1,4-dicarboxamide
NSC55152, complete inhibition at 1 mM
1-[3-(3,4-dichlorophenoxy)propyloxy]-5-isopropylbiguanide
-
i.e. PS-16
1-[3-(4-chlorophenoxy)propyloxy]-5-isopropylbiguanide
-
i.e. PS-33
1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate
1-[4-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
1-[4-(dimethylamino)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
1-[4-[4-(2,4-dichlorophenyl)butyl]phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
-
11H-benzo[b][1]benzazepine
NSC123458, 87% inhibition at 1 mM
2,2'-({6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}diimino)diethanol
-
minimal inhibitory concentration: 0.149 mM
2,3-bis(hydrazino)quinoxaline
-
-
2,4,6-Trinitrobenzenesulfonic acid
-
-
2,4-diamino-5,6-dihydro-6,6-dimethyl-5-(4'-methoxyphenyl)-s-triazine
-
-
2,4-diamino-5-((R)-3-(3,4,5-trimethoxyphenyl)but-1-ynyl)-6-methylpyrimidine
2,4-diamino-5-((S)-3-(3,4,5-trimethoxyphenyl)but-1-ynyl)-6-methylpyrimidine
2,4-diamino-5-(3-(2,5-dimethoxyphenyl)prop-1-ynyl)-6-ethylpyrimidine
i.e. UCP120B, potent enzyme inhibitor of DHFR and bacterial growth, three-dimensional solution structure of the ternary complex with enzyme and NADPH cofactor determined by NMR from 20 mM TES, 50 mM KCl, 10 mM DTT, and 0.5 mM EDTA solution containing 2 mM of each ligand, comparison to the crystal structure of the ternary complex, overview. Analysis of structure and dynamics of the binary inhibitor-enzyme complex
2,4-diamino-5-(3-(3,4,5-trimethoxyphenyl)but-1-ynyl)-6-methylpyrimidine
2,4-diamino-5-(3-(3,4,5-trimethoxyphenyl)but-1-ynyl)pyrimidine
2,4-diamino-5-(3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidine
2,4-diamino-5-(3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-ynyl)-6-methylpyrimidine
2,4-diamino-5-(3-phenylprop-1-ynyl)-6-ethylpyrimidine
2,4-Diamino-5-adamantylpyrimidine
2,4-Diamino-5-benzylpyrimidines
-
-
2,4-diamino-5-isopropyl-6-(phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine
-
-
2,4-diamino-5-isopropyl-6-arylthio-7H-pyrrolo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(1-naphthylthio)furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2',3',5',6'-tetrafluoro-4'-trifluoromethylphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2',5'-dimethoxyphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2',6'-dichlorophenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2',6'-dimethylphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2'-isopropyl-6'-methylphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2'-methoxyphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(2-naphthylthio)furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(3',4'-dimethoxyphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(3'-methoxyphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-6-(4'-methoxyphenylsulfanyl)-furo[2,3-d]pyrimidine
2,4-diamino-5-methyl-butylpyrido[2,3-d]pyrimidine
-
-
2,4-Diamino-5-phenyl-s-triazines
-
-
2,4-diamino-5-propyl-6-(1'-naphthylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine
-
-
2,4-diamino-5-propyl-6-arylthio-7H-pyrrolo[2,3-d]pyrimidine
2,4-diamino-5-[(R)-3-(3-methoxy-5-phenylphenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[(S)-3-(3-methoxy-5-phenylphenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(2,3-dimethoxyphenyl)prop-1-ynyl]-6-ethylpyrimidine
2,4-diamino-5-[3-(2,5-dimethoxyphenyl)prop-1-ynyl]-6-ethylpyrimidine
2,4-diamino-5-[3-(2,5-dimethoxyphenyl)prop-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(2,5-dimethoxyphenyl)prop-1-ynyl]-6-npropylpyrimidine
2,4-diamino-5-[3-(2,5-dimethoxyphenyl)prop-1-ynyl]pyrimidine
2,4-diamino-5-[3-(2-methoxy-5-phenylphenyl)prop-1-ynyl]-6-ethylpyrimidine
-
2,4-diamino-5-[3-(2-phenyl-5-methoxyphenyl)prop-1-ynyl]-6-ethylpyrimidine
-
2,4-diamino-5-[3-(3,4,5-trimethoxyphenyl)-3-methylbut-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3,4,5-trimethoxyphenyl)pent-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3,4,5-trimethoxyphenyl)prop-1-ynyl]-6-ethylpyrimidine
2,4-diamino-5-[3-(3-methoxy-4-(2,6-diisopropylphenyl)phenyl)-but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(3-methoxy-4-(2,6-dimethylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(3-methoxy-4-(2-methylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(3-methoxy-4-phenylphenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(3-methoxy-5-(2,6-diisopropylphenyl)phenyl)-but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-5-[3-(3-methoxy-5-(2,6-dimethylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-(2-methylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-(3,5-dimethylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-(4-methoxyphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-(4-tertbutylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-(6-methylphenyl)phenyl)but-1-ynyl]-6-methylpyrimidine
2,4-diamino-5-[3-(3-methoxy-5-phenylphenyl)but-1-ynyl]-6-methylpyrimidine
-
-
2,4-diamino-6-(2-hydroxydibenz[b,f]azepin-5-yl)methylpteridine
crystallization data
2,4-diamino-6-[(2',5'-dichloroanilino)methyl]pyrido[2,3-d]pyrimidine
2,4-diamino-6-[(3',4',5'-trichloroanilino)methyl]pyrido[2,3-d]pyrimidine
2,4-diamino-6-[N-(2,3,5-trichlorobenzyl)-N-ethylamino]quinazoline
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-cyclopropyl methylamino]quinazoline
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-ethylamino]quinazoline
2,4-diamino-6-[N-(2,5-dimethoxybenzyl)-N-propylamino]quinazoline
2,4-diamino-6-[N-(alpha-naphthyl)-N-ethylamino]quinazoline
2,4-diamino-6-[N-(benzyl)-N-ethylamino]quinazoline
2,4-diamino-6-[N-(beta-naphthyl)-N-cyclopropyl methylamino]-quinazoline
2,4-diamino-6-[N-(beta-naphthyl)-N-ethylamino]quinazoline
2,4-diamino-6-[N-(beta-naphthyl)-N-propylamino]quinazoline
2,4-Dimamino-6-butylpyrido[2,3-d]pyrimidine
-
-
2-(2-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(1-(naphthalen-1-yl)ethyl)amino)ethoxy)ethanol
2-(2-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)[1-(naphthalen-1-yl)ethyl]amino)ethoxy)ethanol
-
2-(3-(2-(hydroxyimino)-2-(pyridine-4-yl)-6,7-dimethylquinoxalin-2-yl)-1-(pyridine-4-yl)ethanone) oxime
i.e. 373265, a dual-site inhibitor, that targets both the substrate and cofactor binding site, docking modelling, overview
2-amino-4-oxo-4,7-dihydro-pyrrolo[2,3-d]pyrimidine-methyl-phenyl-L-glutamic acid
potent enzyme inhibitor with anti-cryptosporidial activity in cell culture, chemical synthesis, overview. The inhibitor forms several hydrogen bonds and van der Waals interactions with the DHFR active site residues, binding close to the nicotinamide ring of NADPH. The carbonyl oxygens of the catalytic D32 hydrogen bond with N3 of the inhibitor forming a fork that holds the inhibitor in optimal position bound to the enzyme
2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
2-amino-5-(4-bromobenzyl)-6-methyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
2-amino-5-(4-chlorobenzyl)-6-methyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
2-amino-5-(4-methoxybenzyl)-6-methyl-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d ]-pyrimidin-4(3H)-one
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-(4-bromophenyl)-7-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol
-
2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d ]pyrimidin-4(3H)-one
2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-methyl-5-(4-nitrobenzyl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
2-amino-6-methyl-5-[4-(trifluoromethoxy)benzyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
-
-
2-amino-8-(1,3-benzodioxol-5-yl)-9-phenyl-1,9-dihydro-6H-purin-6-one
synthesis, overview
2-amino-8-(2-hydroxyphenyl)-9-phenyl-9H-purin-6-ol
-
2-amino-8-(4-methylphenyl)-9-phenyl-9H-purin-6-ol
-
2-amino-9-phenyl-8-(3,4,5-trimethoxyphenyl)-9H-purin-6-ol
-
2-amino-9-phenyl-8-[4-(propan-2-yl)phenyl]-9H-purin-6-ol
-
2-hydroxy-5-nitrobenzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0151 mM
2-methoxybenzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0033 mM
2-[(3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxyphenyl]prop-2-yn-1-yl)oxy]benzoic acid
2-[(5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(1-[tricyclo[4.4.0.02,5]deca-1(10),2(5),6,8-tetraen-8-yl]ethyl)amino]ethanol
2-[(5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(methyl)amino]-2-[tricyclo[4.4.0.02,5]deca-1(10),2(5),6,8-tetraen-7-yl]ethanol
2-[(E)-([2-amino-4-methoxy-6-(phenylamino)pyrimidin-5-yl]imino)methyl]phenol
synthesis, overview
2-[[(4-[[(2-amino-4-oxo-3,4-dihydropyrido[3,2-d]pyrimidin-6-yl)methyl]amino]phenyl)carbonyl]amino]hexanedioic acid
-
-
2-[[1-(3-chlorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl]carbonyl]-N-prop-2-en-1-ylhydrazinecarbothioamide
-
-
3,4-dichlorobenzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0037 mM
3,5-bis(trifluoromethyl)benzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0056 mM
3-((3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxyphenoxy)methyl)benzoic acid
3-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(1-(naphthalen-1-yl)ethyl)amino)propanoic acid
-
3-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)[1-(naphthalen-1-yl)ethyl]amino)propanoic acid
-
3-(2,4-diamino-6-methylpyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol
3-(2,4-diaminophenyl)-1-(3-(4-methylbenzyloxy)phenyl)prop-2-en-1-one
3-(2,4-diaminopyrimidin-5-yl)-1-(4-methoxyphenyl)-prop-2-en-1-one
3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzonitrile
-
3-(trifluoromethyl)benzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0043 mM
3-([(2,4-diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]amino)-4-(2,5-dimethoxyethoxy)phenol
-
ratio of IC50 of human to Mycobacterium tuberculosis enzyme 7.6
3-benzyl-6-[(3,4-dimethoxybenzyl)(methyl)amino]-2-(methylsulfanyl)quinazolin-4(3H)-one
-
50% inhibition at 0.001 mM
3-benzyl-6-[(4-methoxybenzyl)(methyl)amino]-2-(methylsulfanyl)quinazolin-4(3H)-one
-
50% inhibition at 0.0005 mM
3-heptyl-4-hydroxy-1H-naphthalen-2-one
-
IC50: 0.48 mM, 0.03 mM 7,8-dihydrofolate
3-methoxybenzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0038 mM
3-O-(3,4,5-trimethoxybenzoyl)-(-)-epicatechin
-
i.e. TMECG, synthesis of a trimethoxy derivative of epicatechin-3-gallate, which shows high antiproliferative and proapoptotic activity against melanoma. It is a prodrug that is selectively activated by the specific melanocyte enzyme tyrosinase. Upon activation, the compound generates a stable quinone methide product that strongly inhibits dihydrofolate reductase in an irreversible manner. The treatment of melanoma cells affects cellular folate transport and the gene expression of DHFR
3-[(3-(3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxyphenyl)prop-2-yn-1-yl)oxy]benzoic acid
ratio of IC50 values human/Trypanosoma enzyme is 77
3-[(3-[3-[(2,4-diaminopyrimidin-5-yl)methyl]-4-methoxyphenyl]prop-2-yn-1-yl)oxy]benzoic acid
ratio of IC50 values human/Trypanosoma enzyme is 77
3-[[(4-chlorophenyl)sulfonyl]methyl]-N'-hydroxybenzenecarboximidamide
-
-
4,5-dideoxy-5-(2,6-diamino-5-phenylpyrimidin-4-yl)-D-erythro-pentitol
-
selective inhibition, little effect on human or yeast enzyme
4,6-di(5,8-dihydro-1,7-naphthyridin-7(6H)-yl)-N-(4-nitrophenyl)-1,3,5-triazin-2-amine
-
minimal inhibitory concentration: 0.020 mM
4,6-di(morpholin-4-yl)-N-(4-nitrophenyl)-1,3,5-triazin-2-amine
-
minimal inhibitory concentration: 0.0258 mM
4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-(phenylalkylphenyl)-s-triazines
-
bearing a terminal sulfonyl fluoride
4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)-N-(4-sulfamoylphenethyl)-benzamide
-
4-((2,4-diaminopteridin-6-yl)methylamino)-N-(4-sulfamoylphenethyl)benzamide
-
4-((2,4-diaminopteridin-6-yl)methylamino)benzenesulfonamide
-
4-((2,4-diaminopteridin-6-yl)methylamino)benzenesulfonic acid
-
4-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)(1-(naphthalen-1-yl)ethyl)amino)butanoic acid
4-((5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)[1-(naphthalen-1-yl)ethyl]amino)butanoic acid
-
4-((5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl)ethynyl)benzoic acid
4-(2-(4-((2,4-diaminopteridin-6-yl)methylamino)benzamido)ethyl) benzenesulfonic acid
-
4-(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy) butanoic acid
4-(benzyloxy)benzaldehyde thiosemicarbazone
-
-
4-(N-[(2,4-Diamino-6-pteridyl)methyl]-N-methylamino)benzoate
-
-
4-(trifluoromethyl)benzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.013 mM
4-([(2,4-diaminopteridin-6-yl)methyl](methyl)amino)benzoic acid
4-([5-[(2,4-diaminopteridin-6-yl)methyl]-5H-dibenzo[b,f]azepin-2-yl]oxy)butane-1,1-diol
O-(3-carboxypropyl) inhibitor, crystallization data
4-benzyl-N-[3-benzyl-2-(methylsulfanyl)-4-oxo-3,4-dihydroquinazolin-6-yl]benzenesulfonamide
-
50% inhibition at 0.008 mM
4-bromo-N-[2-(methylthio)-4-oxo-3-phenyl-3,4-dihydroquinazolin-6-yl]benzenesulfonamide
-
50% inhibition at 0.002 mM
4-chloro-N-[4-(hydroxycarbamimidoyl)benzyl]benzamide
-
-
4-methylbenzyl N-[amino(imino)methyl]imidothiocarbamate
50% inhibition at 0.0126 mM
4-[(3,5-dichloropyridin-4-yl)oxy]-N'-hydroxybenzenecarboximidamide
-
-
4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]phenol
4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzamido]benzene-1-sulfonyl fluoride
contains a fluorosulfonylphenylaminocarbonyl substitution at R2 on 1-phenyl-6,6-dimethyl-1,3,5-triazine-2,4-diamine ring, and shows the unique behavior of tight-binding and average inhibition, uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate
4-[3-[(2,4-diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]-4-methoxyphenoxy]butanoic acid
50% inhibition of growth in culture at 0.00060 mM
4-[4,6-diamino-2-(4-chlorophenyl)-1,3,5-triazin-1(2H)-yl]benzene-1-sulfonamide
-
4-[4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]butyl]benzenesulfonyl fluoride
uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate
4-[6-[4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]hexyl]benzenesulfonyl fluoride
uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate
4-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy]benzaldehyde thiosemicarbazone
-
-
5,5'-dithiobis(2-nitrobenzoate)
5,6,7,8-tetrahydrofolate
-
non-competitive product inhibition
5-((10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)methyl)-pyrimidine-2,4-diamine
5-((4-methoxyphenylamino)methyl)pyrimidine-2,4-diamine
5-((5H-dibenzo[b,f]azepin-5-yl)methyl)pyrimidine-2,4-diamine
5-((benzo[d]oxazol-2-ylthio)methyl)pyrimidine-2,4-diamine
5-((methyl(naphthalen-1-yl)amino)methyl)pyrimidine-2,4-diamine
5-((naphthalen-1-ylamino)methyl)pyrimidine-2,4-diamine
5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4-diamine
-
IC50: 18 nM, 0.03 mM 7,8-dihydrofolate
5-(3,4-dichlorophenyl)-6-ethylpyrimidine-2,4-diamine
5-(3-chlorophenyl)-6-(3-phenylpropyl)pyrimidine-2,4-diamine
-
5-(3-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
5-(4-bromophenyl)-6-ethylpyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-(4-methoxyphenyl)pyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-isobutylpyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-isopropylpyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-phenylpyrimidine-2,4-diamine
5-(4-chlorophenyl)-6-propylpyrimidine-2,4-diamine
5-(5-[[(2,4-diamino-6-quinazolinyl)methyl](propyl)amino]-2-methoxyphenoxy) pentanoate
5-(methoxymethyl)-6-[[(3,4,5-trimethoxyphenyl)amino]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-ethyl-6-(phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-([[2-methoxy-5-(trifluoromethyl)phenyl]amino]methyl)pyrido[2,3-d]pyrimidine-2,4-diamine
5-ethyl-6-[(4-methoxyphenyl)sulfanyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-[(4-nitrophenyl)sulfanyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-[(naphthalen-1-yl)sulfanyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-[(naphthalen-2-yl)sulfanyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-[(quinolin-8-yl)sulfanyl]-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine
-
5-ethyl-6-[[(2-methoxy-5-methylphenyl)amino]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
5-fluorodeoxyuridine monophosphate
-
5-methoxy-6-[[(3,4,5-trimethoxyphenyl)amino]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
5-methyl-6-[(1,2,3,4-tetrahydronaphthalen-1-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(5,6,7,8-tetrahydronaphthalen-1-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(naphthalen-1-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(naphthalen-1-ylsulfanyl)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(naphthalen-2-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(naphthalen-2-ylsulfanyl)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
5-methyl-6-[(pyren-1-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(quinolin-3-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(quinolin-5-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[(quinolin-6-ylamino)methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
-
-
5-methyl-6-[[(3,4,5-trimethoxyphenyl)amino]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
5-methyl-6-[[(3,4,5-trimethoxyphenyl)sulfanyl]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
5-methyl-6-[[(3-methylphenyl)sulfanyl]methyl]pyrido[2,3-d]pyrimidine-2,4-diamine
5-methyltetrahydrofolate
-
-
5-nitro-6-methylamino-isocytosine
inhibitor of dihydropteroate synthase, also acts on dihydrofolate reductase
5-phenyl-6-((3R,4S)-3,4,5-trihydroxypentyl)pyrimidine-2,4-diamine
-
selective inhibition of Mycobacterium tuberculosis enzyme, little effect on human or yeast enzyme
5-[(E)-benzylideneamino]-6-methoxy-N4-phenylpyrimidine-2,4-diamine
-
5-[(R/S)-2-(2'-methoxyphenyl)-3-methylbutyl]furo[2,3-d]-pyrimidine-2,4-diamine
5-[(R/S)-2-(2'-methoxyphenyl)-3-methylpentyl]furo[2,3-d]pyrimidine-2,4-diamine
5-[(R/S)-2-(2'-methoxyphenyl)-4-methylpentyl]furo[2,3-d]pyrimidine-2,4-diamine
5-[(R/S)-2-(2'-methoxyphenyl)hexyl]furo[2,3-d]pyrimidine-2,4-diamine
5-[(R/S)-2-(2'-methoxyphenyl)pentyl]furo[2,3-d]pyrimidine-2,4-diamine
5-[(R/S)-2-cyclopropyl-2-(2'-methoxyphenyl)ethyl]furo-[2,3-d]pyrimidine-2,4-diamine
5-[(Z/E)-2-(2'-methoxyphenyl)-3-methylbut-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
5-[(Z/E)-2-(2'-methoxyphenyl)-3-methylpent-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
5-[(Z/E)-2-(2'-methoxyphenyl)-4-methylpent-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
5-[(Z/E)-2-(2'-methoxyphenyl)hex-1-en-1-yl]furo[2,3-d]-pyrimidine-2,4-diamine
5-[(Z/E)-2-(2'-methoxyphenyl)pent-1-en-1-yl]furo[2,3-d]-pyrimidine-2,4-diamine
5-[(Z/E)-2-cyclopropyl-2-(2'-methoxyphenyl)vinyl]furo-[2,3-d]pyrimidine-2,4-diamine
5-[3-(2,5-dimethoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-propylpyrimidine-2,4-diamine
-
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamine
-
5-[3-(2-methoxy-2',6'-dimethylbiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(2-methoxy-2'-methylbiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(2-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(3-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(5-methoxy-2',6'-dimethylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(5-methoxy-2'-methylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
-
5-[3-(5-methoxy-3',5'-dimethyl[1,1'-biphenyl]-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(5-methoxy-4'-methylbiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(5-methoxy[1,1'-biphenyl]-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-(biphenyl-3-yl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
-
5-[3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-[(2,4-diamino-5-methylpyrido[2,3-d]pyrimidin-6-yl)methyl]-4-methoxyphenoxy]pentanoic acid
50% inhibition of growth in culture at 0.00167 mM
5-[3-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-methoxyphenyl]but-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
5-[3-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-methoxyphenyl]prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
5-[3-[3-methoxy-5-(morpholin-4-yl)phenyl]but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
5-[3-[3-methoxy-5-(pyridin-4-yl)phenyl]but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
6,6-dimethyl-1-(4-methylphenyl)-1,6-dihydro-1,3,5-triazine-2,4-diamine
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6,6-dimethyl-1-[3-(4-phenylbutyl)phenyl]-1,6-dihydro-1,3,5-triazine-2,4-diamine
uncompetitive versus NADPH, competitive versus 7,8-dihydrofolate
6,7-bis(4-aminophenyl)pteridine-2,4-diamine
NSC61642
6,7-dimethyl-5,6,7,8-tetrahydro-quinazoline-2,4-diamine
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IC50: 790 nM, 0.03 mM 7,8-dihydrofolate
6-((10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)methyl)-1,3,5-triazine-2,4-diamine
6-((10H-phenothiazin-10-yl)methyl)-1,3,5-triazine-2,4-diamine
6-((2-chloro-10H-phenothiazin-10-yl)methyl)-1,3,5-triazine-2,4-diamine