Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(3R,4S)-dihydroxy-5-oxohexylphosphonic acid + NADPH
? + NADP+
-
-
-
-
?
1,2-dideoxy-D-threo-3-hexulose 6-phosphate + NADPH + H+
2-C-ethyl-D-erythritol 4-phosphate + NADP+
-
i.e. 1-methyl-1-deoxy-D-xylulose 5-phosphate or M-DXP, a substrate analogue whichis inactive with the wild-type but active with mutant W204F
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
1-deoxy-D-xylulose 5-phosphate + NADPH
? + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
1-deoxy-D-xylulose-5-phosphate + NADH
methyl-D-erythritol-4-phosphate + NAD+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
1-deoxy-L-erythrulose + NADPH + H+
? + NADP+
-
reaction of the truncated substrate 1-deoxy-L-erythrulose in the presence and absence of phosphite dianion, overview
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH
?
1-fluoro-1-deoxy-D-xylulose-5-phosphate + NADPH
? + NADP+
-
-
-
-
?
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
3-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
-
-
-
-
?
4-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
-
-
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
methyl-D-erythritol-4-phosphate + NADP+
1-deoxy-D-xylulose-5-phosphate + NADPH
-
-
-
-
r
additional information
?
-
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+

2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
the forward reaction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
-
inverse secondary kinetic isotope effects for both 3-[2H] and 4-[2H]-D-1-deoxyxylulose-5-phosphate during DXR-catalyzed isomerization indicates that the enzyme operates through a retro-aldol/aldol mechanism
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NAD(P)H + H+
2-C-methyl-D-erythritol 4-phosphate + NAD(P)+
NADPH is the preferred cofactor
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+

2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second committed step in isopentenyl diphosphate biosynthesis via the plastidial nonmevalonate pathway of isoprenoid biosynthesis, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
involved in the biosynthesis of isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
key enzyme in the bacterial nonmevalonate pathway to terpenoids, DXR introduces the key branching structure required for the eventual production of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the second committed step in the 2C-methyl-D-erythritol 4-phosphate pathway for biosynthesis of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
the forward direction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
NADPH and 2-C-methyl-D-erythritol 4-phosphate bind to the free enzyme and the two bind together to generate a nonproductive ternary complex
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
the forward direction is preferred
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
the enzyme catalyzes the first committed step in the biosynthesis of isopentenyl diphosphate in the plastidial 2C-methyl-D-erythritol 4-phosphate pathway leading to production of forskolin, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
step in the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
i.e. DXP
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose-5-phosphate + NADPH

methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
-
-
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH

?
-
i.e. CF-DXP
-
-
?
1-fluoro-1-deoxy-D-xylulose 5-phosphate + NADPH
?
-
i.e. CF-DXP, results in about 25% of the activity with 1-deoxy-D-xylulose 5-phosphate
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+

? + NADPH
-
in reaction mixtures containing 0.150.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
-
in reaction mixtures containing 0.15-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
-
in reaction mixtures containing 0.15-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana, the reversible reaction can be followed over thousands of reaction cycles. No fragment exchange, and the frequency of exchange, if any, is less than 5 p.p.m. per catalytic cycle
-
-
r
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+

? + NADPH
-
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
-
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
-
reaction mixtures containing 0.23-0.25 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH

? + NADP+
-
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
-
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
-
reaction mixtures containing 0.21-0.34 mM IspC from Escherichia coli, Mycobacterium tuberculosis or Arabidopsis thaliana
-
-
?
additional information

?
-
participation in the control of the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
-
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206216) is able to fold into at least three different conformations
-
-
-
additional information
?
-
-
used for the synthesis of [1-13C1]2C-methyl-D-erythritol 4-phosphate and [3-13C1]2C-methyl-D-erythritol 4-phosphate
-
-
-
additional information
?
-
-
reaction depends on NADPH although it does not involve a reduction step, putative aldehyde intermediate is converted to methyl-D-erythritol-4-phosphate in the presence of NADPH and to 1-deoxy-D-xylolose-5-phosphate in the presence of NADP+
-
-
-
additional information
?
-
-
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid, 1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid, and 1,2-dideoxy-D-hexulose 6-phosphate are poor substrates
-
-
-
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206-216) is able to fold into at least three different conformations
-
-
-
additional information
?
-
C3-C4 substrate binding mode in which DXP chelates a DXR-bound divalent cation via its hydroxyl groups at C3 and C4. The conversion of 1-deoxy-D-xylulose 5-phosphate to 2-methyl-D-erythritol 4-phosphate max include a pseudo-single molecule transition state of the retro-aldol intermediates
-
-
-
additional information
?
-
C3-C4 substrate binding mode in which DXP chelates a DXR-bound divalent cation via its hydroxyl groups at C3 and C4. The conversion of 1-deoxy-D-xylulose 5-phosphate to 2-methyl-D-erythritol 4-phosphate max include a pseudo-single molecule transition state of the retro-aldol intermediates
-
-
-
additional information
?
-
-
DXR has rate-limiting roles in isopentenyl diphosphate and dimethylallyl diphosphate synthesis
-
-
-
additional information
?
-
-
IspC does not catalyze the isomerisation of 1-deoxy-D-xylulose 5-phosphate to give 1-deoxy-L-ribulose 5-phosphate. Active site of IspC is located close to the surface, a flexible loop at the active site (amino acids 206-216) is able to fold into at least three different conformations
-
-
-
additional information
?
-
-
development and evaluation of a high-throughput screening assay for simultaneous selection of inhibitors of the enzyme, overview
-
-
-
additional information
?
-
B9U4U7
DXR is involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
-
additional information
?
-
-
DXR is involved in the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
-
additional information
?
-
DXR can accelerate the biosynthesis of lycopene. DXR is an effective regulatory site for the synthesis and accumulation of diterpenoid compounds such as tanshinone
-
-
-
additional information
?
-
-
substrate synthesis and product identification method, overview
-
-
-
additional information
?
-
-
a retroaldol/aldol mechanism for the DXR catalyzed rearrangement of 1-deoxy-D-xylulose 5-phosphate to 2-C-methyl-D-erythritol 4-phosphate. DXR first cleaves the C3-C4 bond of 1-deoxy-D-xylulose 5-phosphate in a retroaldol manner to generate a three-carbon and a two-carbon phosphate bimolecular intermediate. These two species are then reunited by an aldol reaction to form a new C-C bond, yielding the same aldehyde intermediate methylerythrose phosphate. Subsequent reduction of methylerythrose phosphate by NADPH affords 2-C-methyl-D-erythritol 4-phosphate
-
-
-
additional information
?
-
-
mono-((2S,3S)-3-fluoromethyl-2,4-dihydroxy-3-methyl-butyl) ester is not a substrate for DXR
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
additional information
?
-
Q9XFS9
participation in the control of the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
-
1-deoxy-D-xylulose 5-phosphate + NADPH + H+

2-C-methyl-D-erythritol 4-phosphate + NADP+
Q9XFS9
second committed step in isopentenyl diphosphate biosynthesis via the plastidial nonmevalonate pathway of isoprenoid biosynthesis, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
Q9XFS9
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
P45568
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
involved in the biosynthesis of isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
key enzyme in the bacterial nonmevalonate pathway to terpenoids, DXR introduces the key branching structure required for the eventual production of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
Q5J7B3
the enzyme catalyzes the second committed step in the 2C-methyl-D-erythritol 4-phosphate pathway for biosynthesis of isopentenyl diphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
first committed step in the mevalonate-independent isopentenyl diphosphate biosynthetic pathway, overview
-
-
r
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
O96693
second step of the deoxyxylulose 5-phosphate/methylerythritol 4-phosphate pathway with end product isopentenylphosphate, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
Q6R3F4
the enzyme catalyzes the first committed step in the biosynthesis of isopentenyl diphosphate in the plastidial 2C-methyl-D-erythritol 4-phosphate pathway leading to production of forskolin, overview
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
second step of the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
step in the methylerythritol 4-phosphate pathway
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
C6G1Y8
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
-
-
-
ir
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
(2R,3R)-2,3,4-trihydroxybutyl dihydrogen phosphate
-
IC50: 0.310 mM
(2R,3R)-4-amino-2,3-dihydroxybutyl dihydrogen phosphate
-
very weak inhibitor, IC50: 5 mM, above
(2R,3S)-2,3-dihydroxy-4-(hydroxyamino)-4-oxobutyl dihydrogen phosphate
-
very weak inhibitor, IC50: 5 mM, above
(2R,3S)-4-amino-2,3-dihydroxy-4-oxobutyl dihydrogen phosphate
-
IC50: 0.253 mM
(2S,3R)-2,3-dihydroxy-4-phosphonooxybutyric acid
-
IC50: 0.551 mM
(2S,3R)-dihydroxybutyramide 4-phosphate
-
50% inhibition at 0.09 mM
(2S,3R)-methyl 2,3-dihydroxy-4-phosphonooxybutyrate
-
IC50: 1.024 mM
(3-(hydroxy[(pentafluorophenyl)carbonyl]amino)propyl)phosphonic acid
-
-
(3-(N-hydroxyacetamido)-1-phenyl)propylphosphonic acid
-
92% inhibition at 0.1 mM
(3-[hydroxy(5-oxohexanoyl)amino]propyl)phosphonic acid
-
-
(3-[hydroxy(6-phenylhexanoyl)amino]propyl)phosphonic acid
-
-
(3-[hydroxy(hexadecanoyl)amino]propyl)phosphonic acid
-
-
(3S)-hydroxypentan-2-one 5-phosphate
-
50% inhibition at 0.03 mM
(3S,4R)-3,4-dihydroxy-4-methyl-5-oxohexylphosphonic acid
-
-
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
(4S)-hydroxypentan-2-one 5-phosphate
-
50% inhibition at 0.15 mM
(pyridin-2-ylmethyl)phosphonic acid
-
-
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
i.e. CF3-DXP, very low inhibition
1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
i.e. CF2-DXP, very low inhibition
1,2-dideoxy-D-hexulose 6-phosphate
-
i.e. Et-DXP, very low inhibition
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
1-deoxy-D-xylulose 5-phosphate
-
substrate inhibition
1-deoxy-L-ribulose 5-phosphate
-
50% inhibition at 0.18 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
inhibitor keeps its inhibition capacity in the presence of Triton X-100 and shows antimicrobial activity against Escherichia coli
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
3-(N-hydroxyacetamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
-
-
3-(N-hydroxyformamido)-1-(2-bromophenyl)propylphosphonic acid
-
93% inhibition at 0.1 mM
3-(N-hydroxyformamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
-
-
3-([(1H-indol-3-yl)acetyl]amino)propylphosphonic acid
-
-
3-([2-(methoxycarbonyl)benzoyl]amino)propylphosphonic acid
-
-
3-([3-(1H-indol-3-yl)propanoyl]amino)propylphosphonic acid
-
-
3-([4-(1H-indol-3-yl)butanoyl]amino)propylphosphonic acid
-
-
3-fluoro-1-deoxy-D-xylulose-5-phosphate
-
noncompetitive
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
3-[(2-hydroxybenzoyl)amino]propylphosphonic acid
-
-
3-[(3,4-diethoxybenzoyl)amino]propylphosphonic acid
-
-
3-[(3,4-dimethoxybenzoyl)amino]propylphosphonic acid
-
-
3-[(4-methylpentanoyl)amino]propylphosphonic acid
-
-
3-[(4-phenoxybenzoyl)amino]propylphosphonic acid
-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
4-(N-formyl-N-hydroxy-amino)-butyric acid
-
-
4-fluoro-1-deoxy-D-xylulose-5-phosphate
-
noncompetitive
Arbutus andrachne plant extract
-
-
-
Cercis siliquastrum leaf extract
-
high inhibitory activity
-
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyacetamido)propyl)phosphonate
-
-
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyformamido)propyl)phosphonate
-
-
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate
-
17.9% inhibition
diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate
-
21.4% inhibition
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate
-
11% inhibition
diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate
-
33.5% inhibition
diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate
-
14.1% inhibition
ethyl hydrogen [1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonate
-
-
ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonate
-
-
ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-[2-(pyridin-3-yl)phenyl]propyl]phosphonate
-
20% inhibition at 0.1 mM
fosfoxacin
-
phosphate analogue of fosmidomycin
fosmidomycin analogues
-
synthesis, stereochemistry, and analysis of inhibitory potency of several fosmidomycin analogues, overview
-
FR 900098
-
N-acetyl analogue of fosmidomycin
gallocatechin gallate
-
completely suppresses the activity of DXR at 100 microM, and shows around 50% DXR inhibition at 25 microM
Geranium molle plant extract
-
-
-
Helianthemum ventosum plant extract
-
-
-
Helianthemum vesicarium plant extract
-
-
-
N-hydroxy-N-[2-(3-hydroxy-3-oxido-3,4-dihydro-1H-2,3-benzoxaphosphinin-4-yl)ethyl]acetamide
-
12% inhibition at 0.1 mM
NaCl
-
100 mM, 87% residual activity
NADP+
-
product inhibition
phosphate mono-((2S,3S)-3-fluoromethyl-2,4-dihydroxy-3-methyl-butyl) ester
-
is a weak competitive inhibitor of DXR, most likely due to the steric hindrance caused by the substitution of a fluoromethylgroup for a hydroxyl group. Is not an irreversible inactivator (suicide inhibitor) for DXR, fails to act as a mechanism-based inactivator if the retroaldol/aldol mechanism is operative
phosphoric acid mono-[2-(N-acetyl-N-hydroxy-amino)-ethyl]-ester
-
-
Sarcopoterium spinosum plant extract
-
-
-
sulfamic acid 2-(N-formyl-N-hydroxy-amino)-ethyl ester
-
-
theaflavin-3'-gallate
-
non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
theaflavin-3,3'-digallate
-
non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
theaflavin-3-gallate
-
non-competitive against 1-deoxy-D-xylulose 5-phosphate and un-competitive inhibitors with respect to NADPH
[(1-isoquinolinylamino)methylene]-1,1-bisphosphonate
-
50% inhibition at 0.004 mM
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
-
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
inhibitor keeps its inhibition capacity in the presence of Triton X-100
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
-
[2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid
-
20.0% inhibition
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
-
-
[3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
-
-
[3-(N-acetyl-N-methyl-amino)propyl]-phosphonic acid
-
-
[3-(N-formyl-N-methyl-amino)-propyl]-phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(2-bromophenyl)propyl]phosphonic acid
-
38% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(2-cyanophenyl)propyl]phosphonic acid
-
30% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(2-methylphenyl)propyl]phosphonic acid
-
55% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
[3-[acetyl(hydroxy)amino]-1-[2-(2-hydroxyethyl)phenyl]propyl]phosphonic acid
-
35% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(hydroxymethyl)phenyl]propyl]phosphonic acid
-
36% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(methoxymethyl)phenyl]propyl]phosphonic acid
-
30% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(pyridin-3-yl)phenyl]propyl]phosphonic acid
-
20% inhibition at 0.1 mM
[3-[acetyl(hydroxy)amino]-1-[2-(thiophen-2-yl)phenyl]propyl]phosphonic acid
-
30% inhibition at 0.1 mM
[3-[acetyl(naphthalen-2-ylmethoxy)amino]propyl]phosphonic acid
compound binds to both the NADPH and DXP sites, while whole-cell inhibitory activity is relatively poor
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
[3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid
-
compound binds to Dxr via a non-bisubstrate mechanism. The diethyl ester of [3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid inhibits Mycobacterium tuberculosis growth
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
-
[4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid
-
-
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
[5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid
-
26.8% inhibition
[[(5-chloro-2-pyridinyl)amino]methylene]-1,1-bisphosphonate
-
50% inhibition at 0.007 mM
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid

-
26.8% inhibition
(4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonic acid
-
-
1,2-dideoxy-D-threo-3-hexulose 6-phosphate

-
50% inhibition at 0.63 mM
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
weak, competitive inhibition, a highly conserved tryptophan residue in the flexible loop is blocked by the substrate analog
1-hydroxy-5-phenylpyridin-2(1H)-one

-
minimal inhibitory concentration for growth 0.02 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.1 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.1 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
minimal inhibitory concentration for growth 0.05 mM
1-hydroxy-5-phenylpyridin-2(1H)-one
-
-
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid

-
-
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid

-
-
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid

-
-
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid

-
-
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
-
-
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid

-
-
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid

-
-
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
-
-
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid

-
-
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
-
-
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid

-
-
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
-
-
4-benzylbenzene-1,2-diol

-
minimal inhibitory concentration for growth 0.2 mM
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 1 mM
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 0.2 mM
4-benzylbenzene-1,2-diol
-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol

-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.5 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.2 mM
biphenyl-3,4-diol
-
minimal inhibitory concentration for growth 0.2 mM
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate

-
40.4% inhibition
diethyl (2-[[3-(hydroxymethyl)phenyl]amino]-2-oxoethyl)phosphonate
-
-
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate

-
11.9% inhibition
diethyl [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonate
-
-
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate

-
24.4% inhibition
diethyl [2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonate
-
-
EDTA

-
-
EDTA
-
complete inhibition at 5 mM
Fe2+

-
-
fosmidomycin

-
fosmidomycin
-
50% inhibition at 0.0035 mM
fosmidomycin
-
model for tight-binding mode of inhibition
fosmidomycin
-
acts by binding strongly to DXR as a slow tight-binding inhibitor, inhibitor-enzyme interaction and structure analysis for design of inhibitors, possibly mimics a transition state in the reaction coordinate of the substrate, the initial rapid equilibrium is subject to negative cooperativity, overview
fosmidomycin
-
a phosphonic metabolite from Streptomyces rubellomurinus
fosmidomycin
-
a natural product isolated from Streptomyces lavendulae
fosmidomycin
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteria and other organisms
fosmidomycin
-
a natural antibiotic from Streptomyces lavendulae, a specific, mixed type inhibitor, the N-formyl-N-hydroxy amino headgroup of fosmidomycin coordinates Mg2+ ion forming an octahedral complex with active site residues Asp157, Glu159, and Glu241 and a critical binding site water molecule, residue His219 is essential for placing fosmidomycin in the active site for optimal catalysis, mechanism, overview, NADPH has a vital role in tight binding of the inhibitor within the enzyme active site
fosmidomycin
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 301 nM
fosmidomycin
-
a natural product isolated from Streptomyces lavendulae
fosmidomycin
IC50: 450 nM, recombinant enzyme, inhibition of growth and forskolin production in vivo
fosmidomycin
-
potent inhibitor but with very short half-life in plasma and low oral availability
FR-900098

-
fosmidomycin homologue
FR-900098
-
fosmidomycin homologue
FR900098

-
specific inhibition
FR900098
-
N-acetyl homologue of fosmidomycin
FR900098
-
fosmidomycin homologue
FR900098
-
an acetyl analogue of fosmidomycin
FR900098
analysis of parasite growth in infected cultured erythrocytes. 50% growth inhibition at about 118 nM
FR900098
-
an acetyl analogue of fosmidomycin
FR900098
-
N-acetyl analogue of fosmidomycin
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid

-
43.9% inhibition
[2-[(3-hydroxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid

-
17.8% inhibition
[2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

-
-
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

-
-
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
-
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid

-
49.2% inhibition
[4-[(3-hydroxyphenyl)amino]-4-oxobutyl]phosphonic acid
-
-
additional information

-
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid, 1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid, and 1,2-dideoxy-D-hexulose 6-phosphate are poor inhibitors, most likely because of the increase in steric bulk at C1
-
additional information
-
inhibitor design and synthesis, overview
-
additional information
-
neither the sulfone (N-hydroxy-N-[3-(alkylsulfonyl)propyl]acetamides) nor the sulfonamide derivatives (N-hydroxy-N-(3-sulfamoylpropyl) acetamide and N-hydroxy-N-(3-(N-alkylsulfamoyl)propyl)acetamide) of FR900098 display any significant inhibitory activity against DXR at a concentration of 0.03 mM. Importance of the negative charge for the binding of fosmidomycin-like inhibitors to DXR. Uncharged molecules are virtually inactive whereas derivatives that possess only one instead of two negative charges are markedly less active. It is possible to regain some of the activity that is lost by the reduction of the charge by occupation of hitherto unexploited areas of the enzyme
-
additional information
-
inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl (4-[[3-(hydroxymethyl)phenyl]amino]-4-oxobutyl)phosphonate, diethyl [5-[(3-hydroxyphenyl)amino]-5-oxopentyl]phosphonate, [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonic acid, [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, [5-[(3-methoxyphenyl)amino]-5-oxopentyl]phosphonic acid, diethyl [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonate, [4-[(3-bromophenyl)amino]-4-oxobutyl]phosphonic acid, and [5-[(3-bromophenyl)amino]-5-oxopentyl]phosphonic acid
-
additional information
-
no substrate inhibition by 2-C-methyl-D-erythritol 4-phosphate, NADPH or NADP+
-
additional information
-
development and evaluation of a high-throughput screening spectrometric assay, measuring Dxr activity of Dxr coupled with 1-deoxy-D-xylulose-5-phosphate synthase, Dxs, activity, for simultaneous selection of inhibitors of the enzyme, overview
-
additional information
-
design, synthesis, and X-ray crystallographic studies of alpha-aryl 3,4-dichlorophenyl-substituted fosmidomycin analogues as enzyme inhibitors. The introduction of a 3,4-dichlorophenyl group in the Calpha-position relative to the phosphonate group produces analogues that have a higher in vitro antimalarial activity than fosmidomycin
-
additional information
-
use of the Dxr-fosmidomycin cocrystal structure to design bisubstrate ligands to bind to both the 1-deoxy-D-xylulose-5-phosphate and NADPH sites
-
additional information
-
design and development of inhibitors, structure and docking modeling, overview
-
additional information
-
pyridine-containing fosmidomycin derivative inhibitor design and development using quantitative structure?activity relationship and crystallographic studies, synthesis, overview
-
additional information
-
inhibitory potencies of a series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts as analogues of the potent DXR inhibitor fosmidomycin, effects of the carboxamide N-substituents and the length of the methylene linker, in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays, overview. Molecular modelling and simulated docking studies. No or poor inhibition by diethyl [3-[(3-hydroxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-methoxyphenyl)amino]-2-oxoethyl]phosphonate, diethyl [3-[(3-methoxyphenyl)amino]-3-oxopropyl]phosphonate, diethyl [2-[(3-bromophenyl)amino]-2-oxoethyl]phosphonate, diethyl (3-[[3-(hydroxymethyl)phenyl]amino]-3-oxopropyl)phosphonate, [4-[(3-methoxyphenyl)amino]-4-oxobutyl]phosphonic acid, and [2-[(3-cyanophenyl)amino]-2-oxoethyl]phosphonic acid
-
additional information
-
inhibitor design and synthesis, structure-activity relationship profile for the inhibition of TgDXR, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.69
(3R,4S)-dihydroxy-5-oxohexylphosphonic acid
-
-
1.3
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
0.0031 - 12
1-deoxy-D-xylulose 5-phosphate
0.004 - 0.24
1-deoxy-D-xylulose-5-phosphate
53
1-deoxy-L-erythrulose
-
pH 7.5, 25°C, recombinant enzyme in absence or presence of phosphite dianion
0.227
1-fluoro-1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.1
1-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.084 - 0.972
2-C-methyl-D-erythritol 4-phosphate
0.00537
3-[2H]-D-1-deoxyxylulose-5-phosphate
-
-
0.00423
4-[2H]-D-1-deoxyxylulose-5-phosphate
-
-
0.042 - 0.294
methyl-D-erythritol-4-phosphate
additional information
additional information
-
0.0031
1-deoxy-D-xylulose 5-phosphate

-
-
0.0255
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 30°C, recombinant enzyme
0.04
1-deoxy-D-xylulose 5-phosphate
pH 7.5, 50°C
0.045
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.0471
1-deoxy-D-xylulose 5-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.05
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.06
1-deoxy-D-xylulose 5-phosphate
-
with 1 mM CoCl2
0.081
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant His-tagged enzyme
0.099
1-deoxy-D-xylulose 5-phosphate
-
with 1 mM MgCl2
0.1037
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 22°C
0.11
1-deoxy-D-xylulose 5-phosphate
pH 7.5, 85°C
0.115
1-deoxy-D-xylulose 5-phosphate
-
pH 7.5, 25°C, recombinant enzyme
0.132
1-deoxy-D-xylulose 5-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
0.137
1-deoxy-D-xylulose 5-phosphate
-
wild-type, pH 7.5, 25°C
0.147
1-deoxy-D-xylulose 5-phosphate
pH 8.0, 37°C, recombinant enzyme
0.17
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant wild-type enzyme
0.222
1-deoxy-D-xylulose 5-phosphate
pH 7.8, 37°C
0.25
1-deoxy-D-xylulose 5-phosphate
-
with 1 mM MnCl2
0.3
1-deoxy-D-xylulose 5-phosphate
-
-
0.34
1-deoxy-D-xylulose 5-phosphate
-
-
0.39
1-deoxy-D-xylulose 5-phosphate
-
mutant W203Y, pH 7.5, 25°C
0.42
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
1.015
1-deoxy-D-xylulose 5-phosphate
-
mutant W203F, pH 7.5, 25°C
2.9
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204L
5
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204V
12
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204A
0.004
1-deoxy-D-xylulose-5-phosphate

-
cosubstrate NADPH, presence of Co2+, pH 7.5, 25°C
0.042
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADPH, presence of Mg2+, pH 7.5, 25°C
0.05
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Co2+, pH 7.5, 25°C
0.061
1-deoxy-D-xylulose-5-phosphate
-
-
0.063
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Co2+
0.073
1-deoxy-D-xylulose-5-phosphate
-
pH 7.7, presence of 1 mM MnCl2
0.097
1-deoxy-D-xylulose-5-phosphate
-
pH 7.7, presence of 3 mM MgCl2
0.1
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADPH, presence of Mn2+, pH 7.5, 25°C
0.134
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Mg2+
0.195
1-deoxy-D-xylulose-5-phosphate
-
pH 7.5, 37°C, presence of 1 mM Mn2+
0.21
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Mg2+, pH 7.5, 25°C
0.24
1-deoxy-D-xylulose-5-phosphate
-
cosubstrate NADH, presence of Mn2+, pH 7.5, 25°C
0.084
2-C-methyl-D-erythritol 4-phosphate

-
pH 7.5, 25°C, recombinant enzyme
0.174
2-C-methyl-D-erythritol 4-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.972
2-C-methyl-D-erythritol 4-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
0.042
methyl-D-erythritol-4-phosphate

-
presence of Mg2+, pH 7.5, 25°C
0.158
methyl-D-erythritol-4-phosphate
-
pH 7.7, presence of 3 mM MgCl2
0.294
methyl-D-erythritol-4-phosphate
-
pH 7.7, presence of 1 mM MnCl2
0.05
NADH

-
presence of Co2+, pH 7.5, 25°C
0.26
NADH
-
presence of Mn2+, pH 7.5, 25°C
0.41
NADH
-
presence of Mg2+, pH 7.5, 25°C
0.17
NADP+

-
presence of Mg2+, pH 7.5, 25°C
0.42
NADP+
-
pH 7.5, 25°C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
0.47 - 1
NADP+
pH 8.0, 37°C, recombinant pseudomature enzyme
0.561
NADP+
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.0004
NADPH

-
presence of Co2+, pH 7.5, 25°C
0.0005
NADPH
-
pH 7.6, 37°C, recombinant enzyme
0.001
NADPH
-
pH 7.5, 37°C, presence of 1 mM Co2+
0.0028
NADPH
pH 7.5, 50°C
0.0033
NADPH
-
presence of Mn2+, pH 7.5, 25°C
0.0033
NADPH
-
pH 7.5, 37°C, presence of 1 mM Mn2+
0.005
NADPH
-
presence of Mg2+, pH 7.5, 25°C
0.005
NADPH
-
pH 7.5, 37°C, presence of 1 mM Mg2+
0.007
NADPH
-
with 1 mM MnCl2
0.009
NADPH
-
with 1 mM CoCl2
0.0098
NADPH
-
pH 7.5, 25°C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
0.01
NADPH
-
pH 7.5, 25°C, recombinant enzyme
0.0105
NADPH
pH 7.5, 85°C
0.0127
NADPH
pH 7.8, 37°C
0.0133
NADPH
-
pH 7.8, 22°C
0.02
NADPH
-
with 1 mM MgCl2
0.0297
NADPH
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.03
NADPH
pH 8.0, 37°C, recombinant pseudomature enzyme
0.0825
NADPH
pH 8.0, 37°C, recombinant enzyme
additional information
additional information

-
steady-state and single-turnover kinetics, primary kinetic isotope effects, overview
-
additional information
additional information
-
kinetics, recombinant His-tagged wild-type and mutant enzymes
-
additional information
additional information
-
transient kinetics and kinetic mechanism, stopped-flow fluorescence measurements, overview. Kinetics of pre-steady-state reactions and steady-state kinetics, comparison of simulated and experimental values, burst kinetics model for pre-steady-state kinetics
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.04
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
0.16 - 38
1-deoxy-D-xylulose 5-phosphate
0.00086 - 0.00155
1-deoxy-L-erythrulose
37
1-fluoro-1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.95 - 1.6
2-C-methyl-D-erythritol 4-phosphate
0.16
1-deoxy-D-xylulose 5-phosphate

-
pH 7.8, 37°C, recombinant mutant W204A
0.26
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204L
0.54
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204V
1.59
1-deoxy-D-xylulose 5-phosphate
-
mutant W203F, pH 7.5, 25°C
1.7
1-deoxy-D-xylulose 5-phosphate
pH 7.8, 37°C
2
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 22°C
3.54
1-deoxy-D-xylulose 5-phosphate
-
mutant W203Y, pH 7.5, 25°C
4.2
1-deoxy-D-xylulose 5-phosphate
-
wild-type, pH 7.5, 25°C
4.4
1-deoxy-D-xylulose 5-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
5.25
1-deoxy-D-xylulose 5-phosphate
-
pH 7.5, 25°C, recombinant enzyme
5.3
1-deoxy-D-xylulose 5-phosphate
-
-
10
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant mutant W204F
13.2
1-deoxy-D-xylulose 5-phosphate
-
-
13.7
1-deoxy-D-xylulose 5-phosphate
-
-
16.1
1-deoxy-D-xylulose 5-phosphate
-
-
17
1-deoxy-D-xylulose 5-phosphate
-
pH 7.8, 37°C, recombinant wild-type enzyme
29
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
33
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant His-tagged enzyme
38
1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.00086
1-deoxy-L-erythrulose

-
pH 7.5, 25°C, recombinant enzyme in presence of phosphite dianion
0.00155
1-deoxy-L-erythrulose
-
pH 7.5, 25°C, recombinant enzyme in absence of phosphite dianion
0.95
2-C-methyl-D-erythritol 4-phosphate

-
pH 7.5, 25°C, recombinant enzyme
1.6
2-C-methyl-D-erythritol 4-phosphate
pH 8.0, 37°C, recombinant pseudomature enzyme
0.95
NADP+

-
pH 7.5, 25°C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
1.6
NADP+
pH 8.0, 37°C, recombinant pseudomature enzyme
0.29
NADPH

pH 7.5, 50°C
4.4
NADPH
pH 8.0, 37°C, recombinant pseudomature enzyme
5.25
NADPH
-
pH 7.5, 25°C, recombinant enzyme
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.0041
(pyridin-2-ylmethyl)phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
2
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37°C, recombinant enzyme
3.4
1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37°C, recombinant enzyme
6.2
1,2-dideoxy-D-hexulose 6-phosphate
-
pH 7.6, 37°C, recombinant enzyme
0.63
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37°C, recombinant wild-type enzyme
1.1
1-deoxy-D-xylulose 5-phosphate
-
pH 7.9, 30°C, recombinant His-tagged enzyme
0.0014 - 0.0256
1-hydroxy-5-phenylpyridin-2(1H)-one
0.444
3-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.24
4-(N-formyl-N-hydroxy-amino)-butyric acid
-
pH 7.5, 37°C
0.0224
4-benzylbenzene-1,2-diol
-
pH not specified in the publication, temperature not specified in the publication
0.733
4-fluoro-1-deoxy-D-xylulose-5-phosphate
-
-
0.0447
biphenyl-3,4-diol
-
pH not specified in the publication, temperature not specified in the publication
0.000019
fosfoxacin
-
pH 7.5, 37°C
0.0000021 - 0.00097
fosmidomycin
0.000048 - 0.0009
FR900098
0.000002
phosphoric acid mono-[2-(N-acetyl-N-hydroxy-amino)-ethyl]-ester
-
pH 7.5, 37°C
2.8
sulfamic acid 2-(N-formyl-N-hydroxy-amino)-ethyl ester
-
pH 7.5, 37°C
0.0222 - 0.0224
theaflavin-3'-gallate
0.0133 - 0.0182
theaflavin-3,3'-digallate
0.0247 - 0.03
theaflavin-3-gallate
0.0021
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000077
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
3.6
[3-(N-acetyl-N-methyl-amino)propyl]-phosphonic acid
-
pH 7.5, 37°C
5
[3-(N-formyl-N-methyl-amino)-propyl]-phosphonic acid
-
pH 7.5, 37°C
0.00022
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.0000019 - 0.00097
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.000013 - 0.00053
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.000085 - 0.00093
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.000013 - 0.000087
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.0000089 - 0.000079
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.00048 - 0.0015
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
2.4
[4-(hydroxyamino)-4-oxobutyl]phosphonic acid
-
pH 7.5, 37°C
additional information
additional information
-
inhibition kinetics
-
0.0014
1-hydroxy-5-phenylpyridin-2(1H)-one

-
pH not specified in the publication, temperature not specified in the publication
0.0256
1-hydroxy-5-phenylpyridin-2(1H)-one
-
pH 7.6, 30°C, recombinant enzyme
0.0000021
fosmidomycin

-
-
0.000014
fosmidomycin
-
mutant W203Y, pH 7.5, 25°C
0.000021
fosmidomycin
-
pH 7.5, 22°C
0.000034
fosmidomycin
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.000057
fosmidomycin
-
pH 7.5, 37°C
0.00006
fosmidomycin
-
mutant W203F, pH 7.5, 25°C
0.000085
fosmidomycin
pH 8.0, 37°C, recombinant pseudomature enzyme
0.00009
fosmidomycin
-
pH 7.6, 30°C, recombinant enzyme
0.000093
fosmidomycin
-
wild-type, pH 7.5, 25°C
0.0000989
fosmidomycin
-
pH 7.8, 22°C
0.00097
fosmidomycin
pH 7.8, 37°C
0.000048
FR900098

-
pH 7.6, 30°C, recombinant enzyme
0.00017
FR900098
pH 7.8, 37°C
0.0009
FR900098
-
pH 7.5, 37°C
0.0222
theaflavin-3'-gallate

-
substrate 1-deoxy-D-xylulose 5-phosphate, pH 7.4, 37°C
0.0224
theaflavin-3'-gallate
-
substrate NADPH, pH 7.4, 37°C
0.0133
theaflavin-3,3'-digallate

-
substrate 1-deoxy-D-xylulose 5-phosphate, pH 7.4, 37°C
0.0182
theaflavin-3,3'-digallate
-
substrate NADPH, pH 7.4, 37°C
0.0247
theaflavin-3-gallate

-
substrate NADPH, pH 7.4, 37°C
0.03
theaflavin-3-gallate
-
substrate 1-deoxy-D-xylulose 5-phosphate , pH 7.4, 37°C
0.0000019
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

-
pH 7.5, 22°C
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
0.00097
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000013
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

-
pH 7.5, 22°C
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
0.00053
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.000085
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

-
pH 7.5, 22°C
0.00093
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd8
0.000013
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

-
pH 7.5, 22°C
0.000055
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
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
0.0000089
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

-
pH 7.5, 22°C
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
0.000079
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
-
pH 7.6, 30°C, recombinant enzyme
0.00048
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

-
pH 7.5, 22°C
0.0015
[3-[formyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd7
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.31
(2R,3R)-2,3,4-trihydroxybutyl dihydrogen phosphate
Escherichia coli
-
IC50: 0.310 mM
5
(2R,3R)-4-amino-2,3-dihydroxybutyl dihydrogen phosphate
Escherichia coli
-
very weak inhibitor, IC50: 5 mM, above
5
(2R,3S)-2,3-dihydroxy-4-(hydroxyamino)-4-oxobutyl dihydrogen phosphate
Escherichia coli
-
very weak inhibitor, IC50: 5 mM, above
0.253
(2R,3S)-4-amino-2,3-dihydroxy-4-oxobutyl dihydrogen phosphate
Escherichia coli
-
IC50: 0.253 mM
0.551
(2S,3R)-2,3-dihydroxy-4-phosphonooxybutyric acid
Escherichia coli
-
IC50: 0.551 mM
1.024
(2S,3R)-methyl 2,3-dihydroxy-4-phosphonooxybutyrate
Escherichia coli
-
IC50: 1.024 mM
0.0013
(3-(hydroxy[(pentafluorophenyl)carbonyl]amino)propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30°C
0.0074
(3-(N-hydroxyacetamido)-1-phenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.0054
(3-[hydroxy(5-oxohexanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30°C
0.0051
(3-[hydroxy(6-phenylhexanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30°C
0.0056
(3-[hydroxy(hexadecanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30°C
0.03
(3S,4R)-3,4-dihydroxy-4-methyl-5-oxohexylphosphonic acid
Escherichia coli
-
-
0.0038 - 0.0061
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
0.0093 - 0.02
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0096 - 0.012
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0004 - 0.001
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
0.019 - 0.02
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
0.0007
3-(N-hydroxyacetamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.0056
3-(N-hydroxyformamido)-1-(2-bromophenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.00015
3-(N-hydroxyformamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.03
3-([(1H-indol-3-yl)acetyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([2-(methoxycarbonyl)benzoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([3-(1H-indol-3-yl)propanoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.03
3-([4-(1H-indol-3-yl)butanoyl]amino)propylphosphonic acid
Escherichia coli
-
-
0.012 - 0.014
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
0.03
3-[(2-hydroxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(3,4-diethoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(3,4-dimethoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(4-methylpentanoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.03
3-[(4-phenoxybenzoyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.0033 - 0.0071
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
0.0029 - 0.0051
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
0.0066 - 0.017
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
0.1
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyacetamido)propyl)phosphonate
Mycobacterium tuberculosis
-
above, pH 7,5, 22°C
0.1
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyformamido)propyl)phosphonate
Mycobacterium tuberculosis
-
above, pH 7,5, 22°C
0.038
ethyl hydrogen [1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonate
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.022
ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonate
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.000032 - 107
fosmidomycin
0.000018 - 0.000051
FR-900098
0.000035 - 0.118
FR900098
0.0031 - 0.0044
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
0.0021
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid 3-methylbutyl ester
Escherichia coli
-
at 0.03 mM
0.0024
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-1-yl-ethyl) ester
Escherichia coli
-
at 0.03 mM
0.0016
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono(2-naphthalen-2-yl-ethyl) ester
Escherichia coli
-
at 0.03 mM
0.0039
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-butyl ester
Escherichia coli
-
at 0.03 mM
0.016
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid mono-n-propyl ester
Escherichia coli
-
at 0.03 mM
0.05
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monomethyl ester
Escherichia coli
-
at 0.03 mM
0.00049
[3-(acetyl(hydroxy)amino)propyl]phosphonic acid monophenethyl ester
Escherichia coli
-
at 0.03 mM
0.023
[3-(acetyl(hydroxy)amino)propyl]phosphonic monoethyl ester
Escherichia coli
-
at 0.03 mM
0.21
[3-[acetyl(hydroxy)amino]-1-(2-bromophenyl)propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.205
[3-[acetyl(hydroxy)amino]-1-(2-methylphenyl)propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.00031 - 0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00046 - 0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.0017 - 0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
0.15
[3-[acetyl(hydroxy)amino]-1-[2-(2-hydroxyethyl)phenyl]propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.465
[3-[acetyl(hydroxy)amino]-1-[2-(hydroxymethyl)phenyl]propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22°C
0.00018 - 0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
0.00017 - 0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
0.0178
[3-[hydroxy(3-phenylpropanoyl)amino]propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0038
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide

Escherichia coli
Q1RG16
pH 7.5, 37°C
0.0061
2-[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-hydroxyacetamide
Escherichia coli
Q1RG16
presence of 0.01% Triton X-100, pH 7.5, 37°C
0.0093
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid

Plasmodium falciparum
-
-
0.02
3-(hydroxy([(2-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.0096
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid

Plasmodium falciparum
-
-
0.012
3-(hydroxy([(3-methylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.0004
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid

Plasmodium falciparum
-
-
0.001
3-(hydroxy([(4-phenoxybutanoyl)amino]acetyl)amino)propylphosphonic acid
Escherichia coli
-
-
0.019
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid

Escherichia coli
-
-
0.02
3-(hydroxy([(4-phenylbutanoyl)amino]acetyl)amino)propylphosphonic acid
Plasmodium falciparum
-
-
0.012
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid

Plasmodium falciparum
-
-
0.014
3-[(([(3,4-dimethoxyphenyl)acetyl]amino)acetyl)(hydroxy)amino]propylphosphonic acid
Escherichia coli
-
-
0.0033
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid

Plasmodium falciparum
-
-
0.0071
3-[([(cyclopropylcarbonyl)amino]acetyl)(hydroxy)amino]propylphosphonic acid
Escherichia coli
-
-
0.0029
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid

Plasmodium falciparum
-
-
0.0051
3-[hydroxy(([3-(trifluoromethoxy)benzoyl]amino)acetyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.0066
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid

Plasmodium falciparum
-
-
0.017
3-[hydroxy(([4-(1H-indol-3-yl)butanoyl]amino)acetyl)amino]propylphosphonic acid
Escherichia coli
-
-
0.000032
fosmidomycin

Plasmodium falciparum
-
-
0.000035
fosmidomycin
Escherichia coli
-
pH 7.5, 30°C
0.000035
fosmidomycin
Escherichia coli
-
at 0.03 mM
0.00005
fosmidomycin
Escherichia coli
-
-
0.000054
fosmidomycin
Mycobacterium tuberculosis
-
pH 7.5, 25°C, recombinant enzyme
0.00008
fosmidomycin
Mycobacterium tuberculosis
-
pH 7.5, 22°C
0.000247
fosmidomycin
Francisella tularensis
-
pH 7.8, 22°C
0.000301
fosmidomycin
Plasmodium falciparum
O96693
-
0.00031
fosmidomycin
Mycobacterium tuberculosis
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteri
0.00044
fosmidomycin
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00045
fosmidomycin
Plectranthus barbatus
Q6R3F4
IC50: 450 nM, recombinant enzyme, inhibition of growth and forskolin production in vivo
0.00071
fosmidomycin
Yersinia pestis
Q8ZH62
pH 7.8, 37°C
0.00117
fosmidomycin
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.0027
fosmidomycin
Mycobacterium tuberculosis
-
IC50: 310 nM for the forward reaction, 0.0027 mM for the reverse reaction, Gram positive bacteria, including Mycobacterium tuberculosis, are resistant against the antibiotic fosmidomycin, which is an inhibitor of the enzyme from most gram-negative bacteri
93
fosmidomycin
Thermotoga maritima
Q9WZZ1
pH 7.5, 50°C
107
fosmidomycin
Thermotoga maritima
Q9WZZ1
pH 7.5, 85°C
0.000018
FR-900098

Plasmodium falciparum
-
-
0.000051
FR-900098
Escherichia coli
-
-
0.000035
FR900098

Escherichia coli
-
pH 7.5, 30°C
0.000035
FR900098
Escherichia coli
-
at 0.03 mM
0.00016
FR900098
Mycobacterium tuberculosis
-
pH 7.5, 22°C
0.00023
FR900098
Yersinia pestis
Q8ZH62
pH 7.8, 37°C
0.118
FR900098
Plasmodium falciparum
O96693
-
0.0031
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid

Escherichia coli
Q1RG16
pH 7.5, 37°C
0.0044
[(5Z)-5-(3,4-dihydroxybenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
Escherichia coli
Q1RG16
presence of 0.01% Triton X-100, pH 7.5, 37°C
0.00031
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00044
[3-[acetyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00046
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00063
[3-[acetyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.0017
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid

Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.0035
[3-[acetyl(hydroxy)amino]-1-phenylpropyl]phosphonic acid
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid

Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00034
[3-[formyl(hydroxy)amino]-1-(pyridin-3-yl)propyl]phosphonic acid
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
0.00017
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid

Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain Dd2
0.00018
[3-[formyl(hydroxy)amino]-1-(pyridin-4-yl)propyl]phosphonic acid
Plasmodium falciparum
-
pH 7.5, 22°C, IC50 versus proliferation of Plasmodium falciparum strain 3D7
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.