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Literature summary for 2.1.1.45 extracted from

  • Gangjee, A.; Li, W.; Kisliuk, R.L.; Cody, V.; Pace, J.; Piraino, J.; Makin, J.
    Design, synthesis, and X-ray crystal structure of classical and nonclassical 2-amino-4-oxo-5-substituted-6-ethylthieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors and as potential antitumor agents (2009), J. Med. Chem., 52, 4892-4902.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.1.1.45

Inhibitors

Inhibitors Comment Organism Structure
10-propargyl-5,8-dideazafolate
-
 Escherichia coli
10-propargyl-5,8-dideazafolate
-
 Homo sapiens
10-propargyl-5,8-dideazafolate
-
 Toxoplasma gondii
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Escherichia coli
2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Homo sapiens
2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
-
 Toxoplasma gondii
4-amino-N10-methylfolic acid
-
 Escherichia coli
4-amino-N10-methylfolic acid
-
 Homo sapiens
4-amino-N10-methylfolic acid
-
 Toxoplasma gondii
methotrexate
-
 Escherichia coli
methotrexate
-
 Homo sapiens
methotrexate
-
 Toxoplasma gondii
N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
-
 Escherichia coli
N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
-
 Homo sapiens
N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
-
 Toxoplasma gondii
N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid potent inhibitor of thymidylate synthase Escherichia coli
N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid potent inhibitor of thymidylate synthase Homo sapiens
N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid potent inhibitor of thymidylate synthase Toxoplasma gondii
pemetrexed
-
 Escherichia coli
pemetrexed
-
 Homo sapiens
pemetrexed
-
 Toxoplasma gondii
piritrexim
-
 Escherichia coli
piritrexim
-
 Homo sapiens
piritrexim
-
 Toxoplasma gondii
plevitrexed
-
 Escherichia coli
plevitrexed
-
 Homo sapiens
plevitrexed
-
 Toxoplasma gondii
raltitrexed
-
 Escherichia coli
raltitrexed
-
 Homo sapiens
raltitrexed
-
 Toxoplasma gondii
trimethoprim
-
 Escherichia coli
trimethoprim
-
 Homo sapiens
trimethoprim
-
 Toxoplasma gondii
trimetrexate
-
 Escherichia coli
trimetrexate
-
 Homo sapiens
trimetrexate
-
 Toxoplasma gondii

Organism

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5,10-methylenetetrahydrofolate + dUMP
-
 Escherichia coli dihydrofolate + dTMP
-
 ?
5,10-methylenetetrahydrofolate + dUMP
-
 Homo sapiens dihydrofolate + dTMP
-
 ?
5,10-methylenetetrahydrofolate + dUMP
-
 Toxoplasma gondii dihydrofolate + dTMP
-
 ?

Cofactor

Cofactor Comment Organism Structure
N5,N10-methylenetetrahydrofolate
-
 Escherichia coli
N5,N10-methylenetetrahydrofolate
-
 Homo sapiens
N5,N10-methylenetetrahydrofolate
-
 Toxoplasma gondii

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000018
-
-
 Escherichia coli N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
0.000019
-
-
 Escherichia coli 10-propargyl-5,8-dideazafolate
0.000036
-
-
 Toxoplasma gondii N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid
0.00004
-
-
 Escherichia coli N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid
0.00004
-
-
 Homo sapiens N-[4-[(2-amino-6-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)sulfanyl]benzoyl]-L-glutamic acid
0.000054
-
-
 Homo sapiens N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
0.000085
-
-
 Homo sapiens 10-propargyl-5,8-dideazafolate
0.00009
-
-
 Toxoplasma gondii N-[4-[(2-amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl]-L-glutamic acid
0.00022
-
-
 Homo sapiens 2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.00023
-
-
 Homo sapiens 2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.00028
-
-
 Homo sapiens 2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.00038
-
-
 Homo sapiens 2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.00039
-
-
 Homo sapiens 2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.00043
-
-
 Toxoplasma gondii 10-propargyl-5,8-dideazafolate
0.00069
-
-
 Homo sapiens 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
0.00075
-
-
 Homo sapiens 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.001
-
-
 Toxoplasma gondii 2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.001
-
-
 Toxoplasma gondii 2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0011
-
-
 Toxoplasma gondii 2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
0.0011
-
-
 Homo sapiens 2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0012
-
-
 Escherichia coli 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
0.0012
-
-
 Homo sapiens 2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0013
-
-
 Homo sapiens 2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0014
-
-
 Escherichia coli 2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
0.0016
-
-
 Toxoplasma gondii 2-amino-5-[(3,5-dichlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]-pyrimidin-4(3H)-one
0.0017
-
-
 Escherichia coli 2-amino-6-ethyl-5-[(4-nitrophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0017
-
-
 Toxoplasma gondii 2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.0018
-
-
 Toxoplasma gondii 2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0018
-
-
 Escherichia coli 2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.002
-
-
 Escherichia coli 2-amino-6-ethyl-5-(pyridin-4-ylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.002
-
-
 Escherichia coli 2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0022
-
-
 Toxoplasma gondii 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0022
-
-
 Escherichia coli 2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0022
-
-
 Toxoplasma gondii 2-amino-5-[(4-bromophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0023
-
-
 Escherichia coli 2-amino-5-[(3,4-dichlorophenyl)thio]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0023
-
-
 Homo sapiens 2-amino-6-ethyl-5-(2-naphthylthio)thieno[2,3-d]pyrimidin-4(3H)-one
0.0023
-
-
 Escherichia coli 2-amino-5-[(3-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0023
-
-
 Toxoplasma gondii 2-amino-5-[(3,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0025
-
-
 Escherichia coli 2-amino-5-[(4-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0025
-
-
 Toxoplasma gondii 2-amino-5-[(2-chlorophenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0026
-
-
 Toxoplasma gondii 2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0028
-
-
 Toxoplasma gondii pemetrexed
0.0029
-
-
 Escherichia coli 2-amino-6-ethyl-5-[(4-fluorophenyl)sulfanyl]thieno[2,3-d]pyrimidin-4(3H)-one
0.0046
-
-
 Homo sapiens 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.0056
-
-
 Homo sapiens 2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.0084
-
-
 Toxoplasma gondii 2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.0095
-
-
 Homo sapiens pemetrexed
0.023
-
 IC50 above 0.023 mM Escherichia coli 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.023
-
 IC50 above 0.023 mM Toxoplasma gondii 2-amino-5-[(2,5-dimethoxyphenyl)sulfanyl]-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one
0.028
-
-
 Escherichia coli 2-amino-6-ethyl-5-(phenylsulfanyl)thieno[2,3-d]pyrimidin-4(3H)-one
0.076
-
-
 Escherichia coli pemetrexed