Information on EC 1.1.1.267 - 1-deoxy-D-xylulose-5-phosphate reductoisomerase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.1.1.267
-
RECOMMENDED NAME
GeneOntology No.
1-deoxy-D-xylulose-5-phosphate reductoisomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-C-methyl-D-erythritol 4-phosphate + NADP+ = 1-deoxy-D-xylulose 5-phosphate + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
Metabolic pathways
-
-
methylerythritol phosphate pathway I
-
-
methylerythritol phosphate pathway II
-
-
Terpenoid backbone biosynthesis
-
-
isoprenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
2-C-methyl-D-erythritol-4-phosphate:NADP+ oxidoreductase (isomerizing)
The enzyme requires Mn2+, Co2+ or Mg2+ for activity, with the first being most effective. The enzyme from several eubacteria, including Escherichia coli, forms part of an alternative nonmevalonate pathway for terpenoid biosynthesis (for diagram, {terp/nonMVA}). The mechanism has been shown to be a retroaldol/aldol reaction [2].
CAS REGISTRY NUMBER
COMMENTARY hide
210756-42-6
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
from medicinal garden of Guangzhou University of Chinese Medicine, China
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
DXR-like mRNA
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
no activity in Homo sapiens
-
-
-
Manually annotated by BRENDA team
i.e. Plectranthus barbatus
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Vitis vinifera x Vitis vinifera
-
-
-
Manually annotated by BRENDA team
upregulation in root during mycorrhization
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3R,4S)-dihydroxy-5-oxohexylphosphonic acid + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
1,2-dideoxy-D-threo-3-hexulose 6-phosphate + NADPH + H+
2-C-ethyl-D-erythritol 4-phosphate + NADP+
show the reaction diagram
-
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)+
show the reaction diagram
1-deoxy-D-xylulose 5-phosphate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
show the reaction diagram
1-deoxy-D-xylulose-5-phosphate + NADH
methyl-D-erythritol-4-phosphate + NAD+
show the reaction diagram
-
-
-
-
r
1-deoxy-D-xylulose-5-phosphate + NADPH
methyl-D-erythritol-4-phosphate + NADP+
show the reaction diagram
1-deoxy-L-erythrulose + NADPH + H+
? + NADP+
show the reaction diagram
-
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
?
show the reaction diagram
1-fluoro-1-deoxy-D-xylulose-5-phosphate + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
2C-methyl-D-erythritol 4-phosphate + 2C-methyl-D-erythritol 4-phosphate + NADP+
? + NADPH
show the reaction diagram
2C-methyl-D-erythritol 4-phosphate + hydroxyacetone + NADP+
? + NADPH
show the reaction diagram
3-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
-
-
-
?
4-[2H]-D-1-deoxyxylulose-5-phosphate + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
-
-
-
?
glycolaldehyde phosphate + hydroxyacetone + NADPH
? + NADP+
show the reaction diagram
methyl-D-erythritol-4-phosphate + NADP+
1-deoxy-D-xylulose-5-phosphate + NADPH
show the reaction diagram
-
-
-
-
r
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-deoxy-D-xylulose 5-phosphate + NADPH + H+
2-C-methyl-D-erythritol 4-phosphate + NADP+
show the reaction diagram
additional information
?
-
Q9XFS9
participation in the control of the 2-C-methyl-D-erythritol 4-phosphate pathway
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADP+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
activates, a divalent cation is required for activity, can partially substitute for Mn2+
phosphite dianion
-
activation by phosphite dianion
Zn2+
activates, a divalent cation is required for activity, can partially substitute for Mn2+
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
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
-
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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-benzylbenzene-1,2-diol
4-fluoro-1-deoxy-D-xylulose-5-phosphate
-
noncompetitive
Arbutus andrachne plant extract
-
-
-
biphenyl-3,4-diol
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
fosmidomycin analogues
-
synthesis, stereochemistry, and analysis of inhibitory potency of several fosmidomycin analogues, overview
-
FR 900098
-
N-acetyl analogue of fosmidomycin
FR-900098
FR900098
Geranium molle plant extract
-
-
-
Helianthemum ventosum plant extract
-
-
-
Helianthemum vesicarium plant extract
-
-
-
methyl jasmonate
-
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
-
-
[(1-isoquinolinylamino)methylene]-1,1-bisphosphonate
-
50% inhibition at 0.004 mM
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
-
[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-[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
[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
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
chitosan
induces expression; induces expression
methyl jasmonate
salicylic acid
strongly induces DXR in leaves, reaches the highest level after 48 h of the treatment, and gradually decreases after. Is induced by salicylic acid at least at transcriptional level
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.69
(3R,4S)-dihydroxy-5-oxohexylphosphonic acid
-
-
1.3
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37C, 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, 25C, recombinant enzyme in absence or presence of phosphite dianion
0.227
1-fluoro-1-deoxy-D-xylulose 5-phosphate
-
pH 7.6, 37C, 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
0.05 - 0.41
NADH
0.17 - 1
NADP+
0.0004 - 0.0825
NADPH
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
Synechocystis sp.
-
pH 7.8, 37C, 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
Escherichia coli
-
pH 7.6, 37C, recombinant enzyme
0.95 - 1.6
2-C-methyl-D-erythritol 4-phosphate
0.95 - 1.6
NADP+
0.29 - 5.5
NADPH
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7.5 - 50
1-deoxy-D-xylulose 5-phosphate
1263
0.0000292 - 0.000163
1-deoxy-L-erythrulose
17775
11.3
2-C-methyl-D-erythritol 4-phosphate
Mycobacterium tuberculosis
-
pH 7.5, 25C, recombinant enzyme
2166
5.7
NADP+
Mycobacterium tuberculosis
-
pH 7.5, 25C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
10
540
NADPH
Mycobacterium tuberculosis
-
pH 7.5, 25C, recombinant enzyme, with substrate 1-deoxy-D-xylulose 5-phosphate
5
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0041
(pyridin-2-ylmethyl)phosphonic acid
-
pH 7.6, 30C, recombinant enzyme
2
1,1,1-trifluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37C, recombinant enzyme
3.4
1,1-difluoro-1-deoxy-D-xylulose 5-phosphoric acid
-
pH 7.6, 37C, recombinant enzyme
6.2
1,2-dideoxy-D-hexulose 6-phosphate
-
pH 7.6, 37C, recombinant enzyme
0.63
1,2-dideoxy-D-threo-3-hexulose 6-phosphate
-
pH 7.8, 37C, recombinant wild-type enzyme
1.1
1-deoxy-D-xylulose 5-phosphate
-
pH 7.9, 30C, 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, 37C
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, 37C
0.0000021 - 0.0000989
fosmidomycin
0.000048 - 0.0009
FR900098
0.000002
phosphoric acid mono-[2-(N-acetyl-N-hydroxy-amino)-ethyl]-ester
-
pH 7.5, 37C
2.8
sulfamic acid 2-(N-formyl-N-hydroxy-amino)-ethyl ester
-
pH 7.5, 37C
0.0021
[(5-phenylpyridin-2-yl)methyl]phosphonic acid
-
pH 7.6, 30C, recombinant enzyme
0.000077
[1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonic acid
-
pH 7.6, 30C, recombinant enzyme
3.6
[3-(N-acetyl-N-methyl-amino)propyl]-phosphonic acid
-
pH 7.5, 37C
5
[3-(N-formyl-N-methyl-amino)-propyl]-phosphonic acid
-
pH 7.5, 37C
0.00022
[3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonic acid
-
pH 7.6, 30C, 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, 37C
additional information
additional information
-
inhibition kinetics
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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, 30C
0.0074
(3-(N-hydroxyacetamido)-1-phenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22C
0.0054
(3-[hydroxy(5-oxohexanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30C
0.0051
(3-[hydroxy(6-phenylhexanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30C
0.0056
(3-[hydroxy(hexadecanoyl)amino]propyl)phosphonic acid
Escherichia coli
-
pH 7.5, 30C
0.03
(3S,4R)-3,4-dihydroxy-4-methyl-5-oxohexylphosphonic acid
Escherichia coli
-
-
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, 22C
0.0056
3-(N-hydroxyformamido)-1-(2-bromophenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22C
0.00015
3-(N-hydroxyformamido)-1-(3,4-dichlorophenyl)propylphosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22C
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, 22C
0.1
diethyl (1-(3,4-dichlorophenyl)-3-(N-hydroxyformamido)propyl)phosphonate
Mycobacterium tuberculosis
-
above, pH 7,5, 22C
0.038
ethyl hydrogen [1-(3,4-dichlorophenyl)-3-[formyl(hydroxy)amino]propyl]phosphonate
Mycobacterium tuberculosis
-
pH 7,5, 22C
0.022
ethyl hydrogen [3-[acetyl(hydroxy)amino]-1-(3,4-dichlorophenyl)propyl]phosphonate
Mycobacterium tuberculosis
-
pH 7,5, 22C
0.000032 - 107
fosmidomycin
0.000018 - 0.000051
FR-900098
0.000035 - 0.118
FR900098
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, 22C
0.205
[3-[acetyl(hydroxy)amino]-1-(2-methylphenyl)propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22C
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, 22C
0.465
[3-[acetyl(hydroxy)amino]-1-[2-(hydroxymethyl)phenyl]propyl]phosphonic acid
Mycobacterium tuberculosis
-
pH 7,5, 22C
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
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.1
purified recombinant pseudomature enzyme, reverse reaction
3
presence of Mn2+, 50C, pH 7.5
5
presence of Mg2+, 50C, pH 7.5
5.6
purified recombinant pseudomature enzyme, forward reaction
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 8.5
-
-
7.5 - 8
-
-
7.5
-
assay at
7.5 - 7.9
-
forward and reverse reaction
7.5
-
assay at
7.8 - 8.3
recombinant enzyme
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37 - 45
recombinant enzyme
50 - 60
-
-
70
optimum in presence of Mn2+
85
or above, optimum in presence of Mg2+
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35 - 42
90% of maximal activity within this range
40 - 60
-
-
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
high level of mRNA expression for 1-deoxy-D-xylulose 5-phosphate synthase and 2C-methyl-D-erythritol 4-phosphate synthase in leaf and twig
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Acinetobacter baumannii (strain AB307-0294)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Moraxella catarrhalis (strain BBH18)
Moraxella catarrhalis (strain BBH18)
Moraxella catarrhalis (strain BBH18)
Moraxella catarrhalis (strain BBH18)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Yersinia pseudotuberculosis serotype O:3 (strain YPIII)
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39000
-
2 * 39000, SDS-PAGE
41700
-
2 * 41700, calculated and crystallization data
42000
-
4 * 42000, SDS-PAGE
42500
-
x * 42500, SDS-PAGE
42700
-
2 * 42700, calculated
43500
-
sequence analysis
47000
-
x * 47000, SDS-PAGE
50970
-
sequence analysis
51300
x * 51300, calculated
51400
x * 51400, calculated
51600
X * 51600, calculated
54000
x * 54000, recombinant enzyme, SDS-PAGE
63000
-
gel filtration
75000
-
PAGE
76400
-
x * 76400, calculated
94000
-
gel filtration
108000
-
gel filtration
150000
-
gel filtration