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1.5.1.3: dihydrofolate reductase

This is an abbreviated version!
For detailed information about dihydrofolate reductase, go to the full flat file.

Word Map on EC 1.5.1.3

Reaction

5,6,7,8-tetrahydrofolate
+
NADP+
=
7,8-dihydrofolate
 +
NADPH
 +
H+

Synonyms

5,6,7,8-tetrahydrofolate: NADP+ oxidoreductase, 7,8-dihydrofolate reductase, At2g16370, At4g34570, bifunctional dihydrofolate reductase-thymidylate synthase, bifunctional TS-DHFR, BmDHFR, dehydrogenase, tetrahydrofolate, DFR-TS, DFR1, DfrA, DfrB, DHFR, DHFR type IIIC, DHFR-TS, DHFR-TS1, DHFR-TS2, DHFR2, DHFRL1, DHFRLS, dihydrofolate reductase, dihydrofolate reductase-like, dihydrofolate reductase-thymidylate synthase, dihydrofolate reductase:thymidylate synthase, dihydrofolic acid reductase, dihydrofolic reductase, EC 1.5.1.4, ecDHFR, folA, folA3, folic acid reductase, folic reductase, FolM, hDHFR, hDHFR-1, hDHFR-2, HjDHFR, hvDHFR1, hvDHFR2, LAU_0427, LBRM_06_0830, mDHFR, mjDHFR, More, myDHFR, NADPH-dihydrofolate reductase, pcDHFR, PKNH_0509600, ppDHFR, pteridine reductase, pteridine reductase:dihydrofolate reductase, PTR2, R-plasmid-encoded dihydrofolate reductase, R67 DHFR, R67 dihydrofolate reductase, reductase, dihydrofolate, S3DHFR, Smdhfr, Smp 175230, spDHFR, svDHFR, tcptr1, tetrahydrofolate dehydrogenase, THY-1, THY-2, thymidylate synthase-dihydrofolate reductase, thymidylate synthetase-dihydrofolate reductase, Trimethoprim resistance protein, TS-DHFR, WUBG_00817

ECTree

     1 Oxidoreductases
         1.5 Acting on the CH-NH group of donors
             1.5.1 With NAD+ or NADP+ as acceptor
                1.5.1.3 dihydrofolate reductase

KI Value

KI Value on EC 1.5.1.3 - dihydrofolate reductase

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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000082
(-)-epicatechin gallate
-
25°C, pH 7.6
0.00012
(-)-epigallocatechin gallate
-
25°C, pH 7.6
0.0000027
(2E)-1-(1-cyclohexylphthalazin-2(1H)-yl)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]prop-2-en-1-one
pH and temperature not specified in the publication
0.000005
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenoxyphthalazin-2(1H)-yl)prop-2-en-1-one
pH and temperature not specified in the publication
0.0000026
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
pH and temperature not specified in the publication
0.0000045
(2E)-3-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
pH and temperature not specified in the publication
0.0000072
(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
pH and temperature not specified in the publication
0.0000038
(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
pH and temperature not specified in the publication
0.0000071
(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
pH and temperature not specified in the publication
0.0000048
(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
pH and temperature not specified in the publication
0.0000038
(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
pH and temperature not specified in the publication
0.0000035
(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
pH and temperature not specified in the publication
0.0000056
(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
pH and temperature not specified in the publication
0.0000067
(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
pH and temperature not specified in the publication
0.0000062
(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
pH and temperature not specified in the publication
0.0000051
(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
pH and temperature not specified in the publication
0.0000074
(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
pH and temperature not specified in the publication
0.0000038
(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
pH and temperature not specified in the publication
0.0000188
(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
pH and temperature not specified in the publication
0.0000007
(E)-1-(1-cyclopropyl-6,7-dimethoxyphthalazin-2(1H)-yl)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)prop-2-en-1-one
30°C, pH not specified in the publication
-
0.0000012
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-(4-methoxyphenyl)phthalazin-2(1H)-yl)prop-2-en-1-one, (E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
30°C, pH not specified in the publication
-
0.0000012
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-phenylphthalazin-2(1H)-yl)prop-2-en-1-one
-
30°C, pH not specified in the publication
-
0.0000012
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
30°C, pH not specified in the publication
-
0.0000011
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethoxy-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
30°C, pH not specified in the publication
-
0.0000012
(E)-3-(5-((2,4-diaminopyrimidin-5-yl)methyl)-2,3-dimethoxyphenyl)-1-(6,7-dimethyl-1-propylphthalazin-2(1H)-yl)prop-2-en-1-one
30°C, pH not specified in the publication
-
0.000062 - 0.0005
(E)-5-[2-(2-methoxyphenyl)prop-1-en-1-yl]furo[2,3-d]pyrimidine-2,4-diamine
0.00016 - 0.0016
(Z)-5-[2-(2-methoxyphenyl)prop-1-en-1-yl]furo[2,3-d]pyrimidine-2,4-diamine
0.0000115
1,4-phenylenebis(methylene) bis(N-[amino(imino)methyl](imidothiocarbamate))
25°C, pH 7.5
0.01116
1-(3-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.00102
1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.00402
1-(4-ethoxyphenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.02022
1-[3-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.0008802
1-[3-chloro-4-(5-phenylpentyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.0393
1-[4-(aminomethyl)phenyl]-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.0000037
2,4-diamino-5,6-dihydro-6,6-dimethyl-5-(4'-methoxyphenyl)-s-triazine
-
-
0.000097 - 0.00049
2,4-diamino-5-[3-(2-methoxy-5-phenylphenyl)prop-1-ynyl]-6-ethylpyrimidine
0.00043 - 0.00259
2,4-diamino-5-[3-(2-phenyl-5-methoxyphenyl)prop-1-ynyl]-6-ethylpyrimidine
0.00000026 - 0.0000244
2,4-diamino-6-[(2',5'-dichloroanilino)methyl]pyrido[2,3-d]pyrimidine
0.065
2,4-diaminopyrimidine
-
pH 6.0, 25°C recombinant His-tagged enzyme
0.459
2,4-diaminoquinazoline
-
pH 6.0, 25°C recombinant His-tagged enzyme
0.00039 - 0.00489
3-(2,4-diamino-6-methylpyrimidin-5-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol
0.00000003
3-(2-(3-[(2,4-diamino-6-ethylpyrimidin-5-yl)oxy]propoxy)phenyl)propanoic acid
pH 6, temperature not specified in the publication, isolate PKNY146CSP
-
0.000958
3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzonitrile
pH 7.3, 22°C
0.0021
3-O-(3,4,5-trimethoxybenzoyl)-(-)-epicatechin
-
pH 7.4, 25°C
0.0000094
4-((5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl)ethynyl)benzoic acid
pH 7.0
0.0000036 - 0.000049
4-(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy) butanoic acid
0.00000078
4-(N-[(2,4-Diamino-6-pteridyl)methyl]-N-methylamino)benzoate
-
-
0.0000014 - 0.000034
4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]phenol
0.00289
4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)benzamido]benzene-1-sulfonyl fluoride
pH 7.3, 22°C
0.105
4-[4,6-diamino-2-(4-chlorophenyl)-1,3,5-triazin-1(2H)-yl]benzene-1-sulfonamide
pH 7.3, 22°C
0.0000497
4-[4-[3-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]butyl]benzenesulfonyl fluoride
pH 7.3, 22°C
0.0000926
4-[6-[4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1-yl)phenyl]hexyl]benzenesulfonyl fluoride
pH 7.3, 22°C
0.0000003 - 0.0000534
5-(3,4-dichlorophenyl)-6-ethylpyrimidine-2,4-diamine
0.0000008 - 0.0000033
5-(3-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
0.0000003 - 0.000303
5-(4-bromophenyl)-6-ethylpyrimidine-2,4-diamine
0.0000043 - 0.001576
5-(4-chlorophenyl)-6-(4-methoxyphenyl)pyrimidine-2,4-diamine
0.0000003 - 0.000385
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
0.0000003 - 0.000798
5-(4-chlorophenyl)-6-isobutylpyrimidine-2,4-diamine
0.0000003 - 0.000541
5-(4-chlorophenyl)-6-isopropylpyrimidine-2,4-diamine
0.0000029 - 0.003461
5-(4-chlorophenyl)-6-phenylpyrimidine-2,4-diamine
0.0000005 - 0.000359
5-(4-chlorophenyl)-6-propylpyrimidine-2,4-diamine
0.000024 - 0.000188
5-(5-[[(2,4-diamino-6-quinazolinyl)methyl](propyl)amino]-2-methoxyphenoxy) pentanoate
0.15
5-methyltetrahydrofolate
-
-
0.00006 - 0.00077
5-[(R/S)-2-(2'-methoxyphenyl)-3-methylbutyl]furo[2,3-d]-pyrimidine-2,4-diamine
0.00078 - 0.0046
5-[(R/S)-2-(2'-methoxyphenyl)-3-methylpentyl]furo[2,3-d]pyrimidine-2,4-diamine
0.00062 - 0.0053
5-[(R/S)-2-(2'-methoxyphenyl)-4-methylpentyl]furo[2,3-d]pyrimidine-2,4-diamine
0.0033 - 0.012
5-[(R/S)-2-(2'-methoxyphenyl)hexyl]furo[2,3-d]pyrimidine-2,4-diamine
0.0025 - 0.0028
5-[(R/S)-2-(2'-methoxyphenyl)pentyl]furo[2,3-d]pyrimidine-2,4-diamine
0.00006 - 0.00065
5-[(R/S)-2-cyclopropyl-2-(2'-methoxyphenyl)ethyl]furo-[2,3-d]pyrimidine-2,4-diamine
0.00007 - 0.00083
5-[(Z/E)-2-(2'-methoxyphenyl)-3-methylbut-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
0.00007 - 0.0011
5-[(Z/E)-2-(2'-methoxyphenyl)-3-methylpent-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
0.00091 - 0.011
5-[(Z/E)-2-(2'-methoxyphenyl)-4-methylpent-1-en-1-yl]-furo[2,3-d]pyrimidine-2,4-diamine
0.00055 - 0.0043
5-[(Z/E)-2-(2'-methoxyphenyl)hex-1-en-1-yl]furo[2,3-d]-pyrimidine-2,4-diamine
0.00014 - 0.0016
5-[(Z/E)-2-(2'-methoxyphenyl)pent-1-en-1-yl]furo[2,3-d]-pyrimidine-2,4-diamine
0.00008 - 0.0013
5-[(Z/E)-2-cyclopropyl-2-(2'-methoxyphenyl)vinyl]furo-[2,3-d]pyrimidine-2,4-diamine
0.00183 - 0.00752
5-[3-(2,5-dimethoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.0003 - 0.0205
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
0.0002 - 0.00451
5-[3-(2,5-dimethoxyphenyl)prop-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.0016 - 0.0092
5-[3-(2-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.00164 - 0.0117
5-[3-(3-methoxybiphenyl-4-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.00103 - 0.00266
5-[3-(5-methoxybiphenyl-3-yl)but-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.000083 - 0.00131
5-[3-(biphenyl-3-yl)prop-1-yn-1-yl]-6-ethylpyrimidine-2,4-diamine
0.002 - 0.00981
5-[3-methoxy-3-(3,4,5-trimethoxyphenyl)prop-1-yn-1-yl]-6-methylpyrimidine-2,4-diamine
0.00155
6,6-dimethyl-1-(4-methylphenyl)-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.0003591
6,6-dimethyl-1-[3-(4-phenylbutyl)phenyl]-1,6-dihydro-1,3,5-triazine-2,4-diamine
pH 7.3, 22°C
0.0000052 - 0.000038
6-(2-[4-(benzyloxy)phenyl]ethyl)quinazoline-2,4-diamine
0.0000009 - 0.000617
6-ethyl-5-(4-methoxyphenyl)pyrimidine-2,4-diamine
0.00000155 - 0.00000733
6-ethyl-5-phenylpyrimidine-2,4-diamine
0.000064 - 0.00119
6-ethyl-5-[3-(3,4,5-trimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamine
0.00023 - 0.0017
6-ethyl-5-[3-(4-methoxybiphenyl-3-yl)prop-1-yn-1-yl]pyrimidine-2,4-diamine
0.00017 - 0.0341
6-methyl-5-[3-(3,4,5-trimethoxyphenyl)but-1-yn-1-yl]pyrimidine-2,4-diamine
0.00119 - 0.00391
6-methyl-5-[3-(3,4,5-trimethoxyphenyl)pent-1-yn-1-yl]pyrimidine-2,4-diamine
0.000049 - 0.00125
6-methyl-5-[3-(3,4,5-trimethoxyphenyl)prop-1-yn-1-yl]pyrimidine-2,4-diamine
0.00294 - 0.00481
6-methyl-5-[3-methyl-3-(3,4,5-trimethoxyphenyl)but-1-yn-1-yl]pyrimidine-2,4-diamine
0.0000016 - 0.0000118
6-[(3,4-dimethoxyanilino)methyl]-2,4-quinazolinediamine
0.0000019 - 0.000042
6-[2-(4-butoxyphenyl)ethyl]quinazoline-2,4-diamine
0.0000078 - 0.000048
6-[2-(4-ethoxyphenyl)ethyl]quinazoline-2,4-diamine
0.0000076 - 0.000072
6-[2-(4-hexoxyphenyl)ethyl]quinazoline-2,4-diamine
0.0000053 - 0.000269
6-[2-(4-octyloxyphenyl)ethyl]quinazoline-2,4-diamine
0.00000742
7-[(4-aminophenyl)methyl]-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine
pH 7.3, 22°C
0.0000122
7-[5-[(2,4-diaminopyrimidin-5-yl)methyl]-2,3-dimethoxyphenyl]hept-6-ynoic acid
pH 7.0
0.0000000078 - 0.0000021
aminopterin
0.00000023 - 0.0000009
AR-101
0.00000022 - 0.0000035
Ar-102
0.748
atherospermidine
pH 6.0, 28°C, recombinant enzyme
0.00000011 - 8
cycloguanil
0.005
deoxytubulosine
-
-
0.00178
epicatechin-3-O-gallate
-
pH 7.4, 25°C
0.00092
epigallocatechin-3-O-gallate
-
pH 7.4, 25°C
0.0000013 - 0.0000096
ethyl 4-(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy) butanoate
0.000026 - 0.036
folate
0.0000002 - 0.0000026
iclaprim
0.717
isomoschatoline
pH 6.0, 28°C, recombinant enzyme
0.00034
L-erythro-biopterin
-
with 7,8-dihydrofolate
2.615
liriodenine
pH 6.0, 28°C, recombinant enzyme
1.26
melosmine
pH 6.0, 28°C, recombinant enzyme
0.00000000002 - 0.022
methotrexate
0.0000006 - 0.0000241
methyl 4-(2,6-diamino-5-phenylpyrimidin-4-yl)butanoate
0.0000033 - 0.000024
methyl 4-[(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy) methyl]benzene carboxylate
0.0000005 - 0.0000028
methyl 4-[2,6-diamino-5-(3-chlorophenyl)pyrimidin-4-yl]butanoate
0.0000016 - 0.000013
methyl 5-(5-[(2,4-diamino-6-quinazolinyl)methyl]amino-2-methoxyphenoxy) pentanoate
0.00018
N10-formylaminopterin
Tequatrovirus T4
-
-
0.0016
N10-formyldihydrofolate
-
-
0.0018 - 0.3
NADP+
0.000348
nolatrexed
pH 7.4, 25°C, recombinant enzyme
0.009
pegularinine
-
-
0.0000005 - 0.00029
pemetrexed
0.0000039 - 0.000008
piritrexim
0.000045
pralatrexate
-
-
0.0018
Pteroate
-
-
0.0000052 - 0.00035
PY957
0.00000005 - 0.068
pyrimethamine
0.0000082
quinone methide
-
pH 7.4, 25°C
0.0000931 - 0.002
raltitrexed
0.0000021
TMP
pH and temperature not specified in the publication
0.00002
Triampterene
-
-
0.000001 - 0.046
trimethoprim
0.00000023 - 0.000000597
trimetrexate
0.007
tylophorinidine
-
-
-
0.00000044 - 0.0000155
WR99210
additional information
additional information
-