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Literature summary for 1.5.1.3 extracted from

  • Gangjee, A.; Qiu, Y.; Li, W.; Kisliuk, R.L.
    Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates (2008), J. Med. Chem., 51, 5789-5797.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 1.5.1.3

Inhibitors

Inhibitors Comment Organism Structure
2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
-
 Escherichia coli
2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
-
 Homo sapiens
2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
-
 Toxoplasma gondii
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
methotrexate
-
 Escherichia coli
methotrexate
-
 Homo sapiens
methotrexate
-
 Toxoplasma gondii
additional information inhibitor synthesis and molecular modelling Escherichia coli
additional information inhibitor synthesis and molecular modelling Homo sapiens
additional information inhibitor synthesis and molecular modelling Toxoplasma gondii
N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid binding mode, overview Escherichia coli
N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid binding mode, overview Homo sapiens
N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid binding mode, overview Toxoplasma gondii
nolatrexed
-
 Escherichia coli
nolatrexed
-
 Homo sapiens
nolatrexed
-
 Toxoplasma gondii
pemetrexed
-
 Escherichia coli
pemetrexed
-
 Homo sapiens
pemetrexed
-
 Toxoplasma gondii
raltitrexed
-
 Escherichia coli
raltitrexed
-
 Homo sapiens
raltitrexed
-
 Toxoplasma gondii
trimethoprim
-
 Escherichia coli
trimethoprim
-
 Homo sapiens
trimethoprim
-
 Toxoplasma gondii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
7,8-dihydrofolate + NADPH + H+ Escherichia coli
-
 5,6,7,8-tetrahydrofolate + NADP+
-
 ?
7,8-dihydrofolate + NADPH + H+ Toxoplasma gondii
-
 5,6,7,8-tetrahydrofolate + NADP+
-
 ?
7,8-dihydrofolate + NADPH + H+ Homo sapiens
-
 5,6,7,8-tetrahydrofolate + NADP+
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Homo sapiens P00374
-
-
Toxoplasma gondii
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
7,8-dihydrofolate + NADPH + H+
-
 Escherichia coli 5,6,7,8-tetrahydrofolate + NADP+
-
 ?
7,8-dihydrofolate + NADPH + H+
-
 Toxoplasma gondii 5,6,7,8-tetrahydrofolate + NADP+
-
 ?
7,8-dihydrofolate + NADPH + H+
-
 Homo sapiens 5,6,7,8-tetrahydrofolate + NADP+
-
 ?

Synonyms

Synonyms Comment Organism
DHFR
-
 Escherichia coli
DHFR
-
 Toxoplasma gondii
DHFR
-
 Homo sapiens

Cofactor

Cofactor Comment Organism Structure
NADPH
-
 Escherichia coli
NADPH
-
 Toxoplasma gondii
NADPH
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000008
-
-
 Toxoplasma gondii N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid
0.0000088
-
-
 Escherichia coli methotrexate
0.00001
-
-
 Escherichia coli trimethoprim
0.00002
-
-
 Homo sapiens methotrexate
0.00002
-
-
 Homo sapiens N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid
0.000031
-
-
 Toxoplasma gondii 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.000033
-
-
 Toxoplasma gondii methotrexate
0.000034
-
-
 Toxoplasma gondii 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.000038
-
-
 Toxoplasma gondii 2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.000044
-
-
 Toxoplasma gondii 2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.000048
-
-
 Toxoplasma gondii 2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.000056
-
-
 Toxoplasma gondii 2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.000056
-
-
 Toxoplasma gondii 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.000064
-
-
 Toxoplasma gondii 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.00012
-
-
 Toxoplasma gondii 2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
0.0002
-
-
 Escherichia coli N-(4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl)-L-glutamic acid
0.00043
-
-
 Toxoplasma gondii permetrexed
0.00056
-
-
 Homo sapiens 2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0012
-
-
 Escherichia coli 2-amino-6-methyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0015
-
-
 Homo sapiens 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0025
-
-
 Homo sapiens 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.0026
-
-
 Homo sapiens 2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0028
-
-
 Escherichia coli 2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0028
-
-
 Homo sapiens 2-amino-5-[(3,4-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0028
-
-
 Escherichia coli 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0029
-
-
 Homo sapiens 2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.0035
-
-
 Homo sapiens 2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
0.0056
-
-
 Homo sapiens 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.0066
-
-
 Homo sapiens permetrexed
0.0068
-
-
 Toxoplasma gondii trimethoprim
0.022
-
-
 Homo sapiens 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.028
-
-
 Escherichia coli 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.028
-
-
 Escherichia coli 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.032
-
-
 Escherichia coli 2-amino-5-[(4-fluorophenyl)sulfanyl]-6-methylthieno[2,3-d]pyrimidin-4(3H)-one
0.035
-
-
 Escherichia coli 2-amino-4-oxo-6-methyl-5-phenylsulfanylthieno[2,3-d]pyrimidine
0.035
-
-
 Escherichia coli 2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.058
-
-
 Escherichia coli 2-amino-6-methyl-5-(2-naphthylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.23
-
-
 Escherichia coli permetrexed
0.34
-
-
 Homo sapiens trimethoprim