Information on EC 1.5.1.3 - dihydrofolate reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.5.1.3
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RECOMMENDED NAME
GeneOntology No.
dihydrofolate reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
5,6,7,8-tetrahydrofolate + NADP+ = 7,8-dihydrofolate + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
folate transformations II
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N10-formyl-tetrahydrofolate biosynthesis
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tetrahydrofolate biosynthesis
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sulfopterin metabolism
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tetrahydrofolate metabolism
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One carbon pool by folate
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Folate biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
5,6,7,8-tetrahydrofolate:NADP+ oxidoreductase
The enzyme from animals and some micro-organisms also slowly reduces folate to 5,6,7,8-tetrahydrofolate.
CAS REGISTRY NUMBER
COMMENTARY hide
9002-03-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene dhfr-ts
UniProt
Manually annotated by BRENDA team
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Uniprot
Manually annotated by BRENDA team
; expression in Escherichia coli
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Manually annotated by BRENDA team
overview
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
trimethoprim-susceptible strain PC 174 and trimethoprim-resistant strain PC 178
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Enterococcus faecalis R / ATCC 8043
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Manually annotated by BRENDA team
var. durans
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Manually annotated by BRENDA team
Escherichia coli B / ATCC 11303
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Manually annotated by BRENDA team
Escherichia coli MB 1428 / B / ATCC 11303
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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AB986558
GenBank
Manually annotated by BRENDA team
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AB986558
GenBank
Manually annotated by BRENDA team
i.e. Helicoverpa virescens, tobacco budworm
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Manually annotated by BRENDA team
human virus produced in cultured lymphoma derived B-cells
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Manually annotated by BRENDA team
R-plasmid encoded, trimethoprim-resistant
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Manually annotated by BRENDA team
Leishmania braziliensis subsp. viannia
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
2 forms, not genetically determined isozymes
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Pigeon
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Manually annotated by BRENDA team
bifunctional dihydrofolate reductase/thymidylate synthase
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Manually annotated by BRENDA team
protozoa
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UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
trimethoprim-resistant enzyme
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Manually annotated by BRENDA team
methicillin-sensitive and -resistant strains
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Manually annotated by BRENDA team
overview
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
6-hydroxymethylpterin + NADPH
6-hydroxymethyl-7,8-dihydropterin + NADP+
show the reaction diagram
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?
6-methylpterin + NADPH
6-methyl-7,8-dihydropterin + NADP+
show the reaction diagram
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?
7,8-dihydrofolate + acetylpyridine adenine nucleotide, reduced
5,6,7,8-tetrahydrofolate + acetylpyridine adenine nucleotide, oxidized
show the reaction diagram
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?
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
show the reaction diagram
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?
7,8-dihydrofolate + NADP + H+
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
8-methylpterin + NADPH
8-methyl-7,8-dihydropterin + NADP+
show the reaction diagram
D-erythro-7,8-neopterin + NADPH
?
show the reaction diagram
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low activity
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?
D-threo-neopterin + NADPH
?
show the reaction diagram
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low activity
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?
dihydrobiopterin + NADPH
? + NADP+
show the reaction diagram
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10% of the activity with 7,8-dihydrofolate
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?
dihydrofolate + NADPH + H+
tetrahydrofolate + NADP+
show the reaction diagram
dihydropteroate + NADPH
?
show the reaction diagram
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?
folate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
L-erythro-neopterin + NADPH
?
show the reaction diagram
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?
L-threo-7,8-dihydroneopterin + NADPH
?
show the reaction diagram
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low activity
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?
L-threo-neopterin + NADPH
?
show the reaction diagram
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?
pterin + NADPH
7,8-dihydropterin + NADP+
show the reaction diagram
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low activity
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?
xanthopterin + NADPH
?
show the reaction diagram
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low activity
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
7,8-dihydrofolate + NADH + H+
5,6,7,8-tetrahydrofolate + NAD+
show the reaction diagram
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?
7,8-dihydrofolate + NADPH
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
7,8-dihydrofolate + NADPH + H+
5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-acetylpyridine adenine nucleotide
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cs+
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activation of mutant type enzyme at 0.2 mM, decrease of wild type enzyme activity above 0.1 mM
Li+
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activation of mutant type enzyme at 0.2 mM, decrease of wild type enzyme activity above 0.1 mM
Organic mercurials
Ru+
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activation of mutant type enzyme at 0.2 mM, decrease of wild type enzyme activity above 0.1 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(-)-epicatechin gallate
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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
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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
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(2,4-diaminopyrimidin-5-yl)methyl naphthalene-2-sulfonate
(2,5-dimethyl-1,4-phenylene)bis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
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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
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(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenoxyphthalazin-2(1H)-yl)prop-2-en-1-one
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(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
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(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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(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
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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
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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
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i.e, methotrexate, A DHFR inhibitor, binds at the DHFR active site
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(2S)-2-[(5-{methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid
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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)
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minimal inhibitory concentration: 0.003536 mM
1,1'-{6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}bis(4-methylpyrazinediium)
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minimal inhibitory concentration: 0.002418 mM
1,1'-{6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}bis(4-phenylpyrazinediium)
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minimal inhibitory concentration: 0.018 mM
1,3-phenylenebis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
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50% inhibition at 0.000075 mM
1,4-bis-([N-(1-imino-1-guanidino-methyl)]sulfanylmethyl)-3,6-dimethyl-benzene
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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))
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1,6-bis-(4-fluoro-phenyl)-[1,3,5]triazine-2,4-diamine
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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
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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
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1-(4-nitrophenyl)-3-[4-[4-[(4-nitrophenyl)carbamoylamino]phenoxy]phenyl]urea
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NSC80735, complete inhibition at 1 mM
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1-([N-(1-imino-guanidino-methyl)]sulfanylmethyl)-3-trifluoromethyl-benzene
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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
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NSC55152, complete inhibition at 1 mM
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1-[3-(3,4-dichlorophenoxy)propyloxy]-5-isopropylbiguanide
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i.e. PS-16
1-[3-(4-chlorophenoxy)propyloxy]-5-isopropylbiguanide
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i.e. PS-33
1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
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1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
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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
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1-[4-(dimethylamino)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
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1-[4-[4-(2,4-dichlorophenyl)butyl]phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
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11H-benzo[b][1]benzazepine
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NSC123458, 87% inhibition at 1 mM
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2,2'-({6-[(4-nitrophenyl)amino]-1,3,5-triazine-2,4-diyl}diimino)diethanol
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minimal inhibitory concentration: 0.149 mM
2,3-bis(hydrazino)quinoxaline
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2,4,6-Trinitrobenzenesulfonic acid
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2,4-diamino-5,6-dihydro-6,6-dimethyl-5-(4'-methoxyphenyl)-s-triazine
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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
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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
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2,4-diamino-5-isopropyl-6-(phenylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine
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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
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2,4-Diamino-5-phenyl-s-triazines
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-
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
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-
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'-dichloroanilino)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-diaminopyrimidine
2,4-diaminoquinazoline
2,4-Dimamino-6-butylpyrido[2,3-d]pyrimidine
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2,4-Pentanedione
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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
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2-(3-(2-(hydroxyimino)-2-(pyridine-4-yl)-6,7-dimethylquinoxalin-2-yl)-1-(pyridine-4-yl)ethanone) oxime
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i.e. 373265, a dual-site inhibitor, that targets both the substrate and cofactor binding site, docking modelling, overview