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Literature summary for 1.1.1.267 extracted from

  • Xue, J.; Diao, J.; Cai, G.; Deng, L.; Zheng, B.; Yao, Y.; Song, Y.
    Antimalarial and structural studies of pyridine-containing inhibitors of 1-deoxyxylulose-5-phosphate reductoisomerase (2013), ACS Med. Chem. Lett., 4, 278-282.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
drug development 1-deoxy-D-xylulose-5-phosphate reductoisomerase in the nonmevalonate isoprene biosynthesis pathway is a target for developing antimalarial drugs Plasmodium falciparum

Inhibitors

Inhibitors Comment Organism Structure
fosmidomycin
-
Escherichia coli
fosmidomycin
-
Plasmodium falciparum
additional information pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview Plasmodium falciparum
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
Escherichia coli
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
Plasmodium falciparum
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
Escherichia coli
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
Plasmodium falciparum
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
Escherichia coli
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
Plasmodium falciparum
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
Escherichia coli
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
Plasmodium falciparum
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
Escherichia coli
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
Plasmodium falciparum
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
Escherichia coli
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
Plasmodium falciparum

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ activates, can substitute for Mg2+ Escherichia coli
Mg2+ activates, can substitute for Mg2+ Plasmodium falciparum
Mn2+ required, activates Escherichia coli
Mn2+ required, activates Plasmodium falciparum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Escherichia coli
-
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+ Plasmodium falciparum
-
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Plasmodium falciparum O96693
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
Escherichia coli 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
-
Plasmodium falciparum 2-C-methyl-D-erythritol 4-phosphate + NADP+
-
?

Synonyms

Synonyms Comment Organism
1-deoxyxylulose-5-phosphate reductoisomerase
-
Escherichia coli
1-deoxyxylulose-5-phosphate reductoisomerase
-
Plasmodium falciparum
DXR
-
Escherichia coli
DXR
-
Plasmodium falciparum

Cofactor

Cofactor Comment Organism Structure
NADPH
-
Escherichia coli
NADPH
-
Plasmodium falciparum

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000019
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.0000089
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.000013
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.000013
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.000021
-
fosmidomycin pH 7.5, 22°C Plasmodium falciparum
0.000034
-
fosmidomycin pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Escherichia coli
0.000035
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd4 Escherichia coli
0.000042
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd5 Escherichia coli
0.000082
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd6 Escherichia coli
0.000085
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.000087
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd3 Escherichia coli
0.00048
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid pH 7.5, 22°C Plasmodium falciparum
0.00093
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd8 Escherichia coli
0.0015
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd7 Escherichia coli

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00017
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum [3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00018
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum [3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00018
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum [3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00031
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00034
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum [3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00044
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00044
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum fosmidomycin
0.00046
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00063
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00117
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum fosmidomycin
0.0017
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.0035
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7 Plasmodium falciparum [3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

General Information

General Information Comment Organism
metabolism the 1-deoxy-D-xylulose-5-phosphate reductoisomerase is the second enzyme in the nonmevalonate isoprene biosynthesis pathway, catalyzing the reductive isomerization of 1-deoxy-D-xylulose-5-phosphate to 2-methyl-D-erythritol-4-phosphate for making isopentenyl diphosphate and dimethylallyl diphosphate Escherichia coli
metabolism the 1-deoxy-D-xylulose-5-phosphate reductoisomerase is the second enzyme in the nonmevalonate isoprene biosynthesis pathway, catalyzing the reductive isomerization of 1-deoxy-D-xylulose-5-phosphate to 2-methyl-D-erythritol-4-phosphate for making isopentenyl diphosphate and dimethylallyl diphosphate Plasmodium falciparum