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Information on EC 1.17.99.2 - ethylbenzene hydroxylase
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1.17.99.2 ethylbenzene hydroxylaseIUBMB Comments
Involved in the anaerobic catabolism of ethylbenzene by denitrifying bacteria. Ethylbenzene is the preferred substrate; the enzyme from some strains oxidizes propylbenzene, 1-ethyl-4-fluorobenzene, 3-methylpent-2-ene and ethylidenecyclohexane. Toluene is not oxidized. p-Benzoquinone or ferrocenium can act as electron acceptor. Contains molybdopterin, [4Fe-4S] clusters and heme b.
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Word Map
- 1.17.99.2
- molybdenum
-
denitrifying
- aromaticum
- aromatoleum
- azoarcus
-
s-1-phenylethanol
-
oxygen-independent
-
heterotrimer
-
carbocation
-
nonactivated
- biotechnology
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
ethylbenzene dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EBDH
ethylbenzene dehydrogenase
EBDH
-
-
ethylbenzene dehydrogenase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
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ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation, quantitative structure-activity relationship modeling
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ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation, quantum chemical modelling and quantitative structure-activity relationship modelling
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ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
ethylbenzene oxidation mechanism involving active site residue His192, and two one-electron transfers and a radical-type intermediate have lower energy barriers than the corresponding two-electron transfer mechanisms, modeling, overview
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ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation, quantitative structure-activity relationship modeling
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ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
kinetics and mechanism of oxygen-independent hydrocarbon hydroxylation, quantum chemical modelling and quantitative structure-activity relationship modelling
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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-
-
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reduction
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-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
ethylbenzene:acceptor oxidoreductase
Involved in the anaerobic catabolism of ethylbenzene by denitrifying bacteria. Ethylbenzene is the preferred substrate; the enzyme from some strains oxidizes propylbenzene, 1-ethyl-4-fluorobenzene, 3-methylpent-2-ene and ethylidenecyclohexane. Toluene is not oxidized. p-Benzoquinone or ferrocenium can act as electron acceptor. Contains molybdopterin, [4Fe-4S] clusters and heme b.
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CAS REGISTRY NUMBER
COMMENTARY
249614-72-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1S)-1-(4-ethylphenyl)ethanol + H2O + ferricenium
(1S,1'S)-1,1'-(benzene-1,4-diyl)diethanol + ferrocene
-
-
-
-
?
1,2,3,4-tetrahydronaphthalene + H2O + ferricenium
(S)-1,2,3,4-tetrahydronaphthalen-1-ol + ferrocene
-
-
-
-
?
1,2-diethylbenzene + H2O + ferricenium
(S)-1-(2-ethylphenyl)ethanol + ferrocene
-
-
-
-
?
1,4-diethylbenzene + H2O + acceptor
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + acceptor
1,4-diethylbenzene + H2O + acceptor
? + reduced acceptor
-
35% of the activity with ethylbenzene
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-
?
1,4-diethylbenzene + H2O + ferricenium
(S)-1-(4-ethylphenyl)ethanol + ferrocene
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-
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocene
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocenium
1-ethyl-2-methylbenzene + H2O + acceptor
? + reduced acceptor
-
3.8% of the activity with ethylbenzene
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-
?
1-ethyl-2-methylbenzene + H2O + ferricenium
(S)-1-(2-methylphenyl)ethanol + ferrocene
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-
-
-
?
1-ethyl-3-fluorobenzene + H2O + acceptor
? + reduced acceptor
-
15% of the activity with ethylbenzene
-
-
?
1-ethyl-3-methylbenzene + H2O + acceptor
? + reduced acceptor
-
10% of the activity with ethylbenzene
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-
?
1-ethyl-3-methylbenzene + H2O + ferricenium
(S)-1-(3-methylphenyl)ethanol + ferrocene
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-
-
-
?
1-ethyl-4-fluorobenzene + H2O + ferricenium
(S)-1-(4-fluorophenyl)ethanol + ferrocene
-
-
-
-
?
1-ethyl-4-methoxybenzene + H2O + ferricenium
(S)-1-(4-methoxyphenyl)ethanol + ferrocene
-
-
-
-
?
1-ethyl-4-methylbenzene + H2O + acceptor
? + reduced acceptor
-
28% of the activity with ethylbenzene
-
-
?
1-ethyl-4-methylbenzene + H2O + ferricenium
(S)-1-(4-methylphenyl)ethanol + ferrocene
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-
-
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?
2,3-dihydro-1H-indene + H2O + ferricenium
(S)-2,3-dihydro-1H-inden-1-ol + ferrocene
-
-
-
-
?
2-ethyl-1H-pyrrole + H2O + acceptor
? + reduced acceptor
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234.5% of the activity with ethylbenzene
-
-
?
2-ethyl-1H-pyrrole + H2O + ferricenium
(S)-1-(1H-pyrrol-2-yl)ethanol + ferrocene
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-
-
-
?
2-ethyl-aniline + H2O + acceptor
? + reduced acceptor
-
94.5% of the activity with ethylbenzene
-
-
?
2-ethylfuran + H2O + acceptor
? + reduced acceptor
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133.9% of the activity with ethylbenzene
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-
?
2-ethylfuran + H2O + ferricenium
(S)-1-(furan-2-yl)ethanol + ferrocene
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-
-
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?
2-ethylnaphthalene + H2O + acceptor
? + reduced acceptor
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9.3% of the activity with ethylbenzene
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-
?
2-ethylnaphthalene + H2O + ferricenium
(S)-1-(naphthalen-2-yl)ethanol + ferrocene
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-
-
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?
2-ethylnaphthalene + H2O + ferricenium
? + ferrocene
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9.3% activity compared to ethylbenzene
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-
?
2-ethylphenol + H2O + acceptor
2-(1-hydroxyethyl)phenol + reduced acceptor
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-
-
-
?
2-ethylphenol + H2O + acceptor
? + reduced acceptor
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56.7% of the activity with ethylbenzene
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-
?
2-ethylphenol + H2O + ferricenium
2-(1-hydroxyethyl)phenol + ferrocene
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55% activity compared to ethylbenzene
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?
2-ethylphenol + H2O + ferricenium
2-(1-hydroxyethyl)phenol + ferrocenium
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-
-
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?
2-ethylpyrrole + H2O + ferricenium
? + ferrocene
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228% activity compared to ethylbenzene
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?
2-ethylthiophene + H2O + acceptor
? + reduced acceptor
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242.9% of the activity with ethylbenzene
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-
?
2-ethylthiophene + H2O + ferricenium
(S)-1-(thiophen-2-yl)ethanol + ferrocene
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-
-
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?
2-ethylthiophene + H2O + ferricenium
1-thien-2-ylethanol + ferrocene
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236% activity compared to ethylbenzene
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?
2-ethylthiophene + H2O + ferricenium
1-thien-2-ylethanol + ferrocenium
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-
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?
2-ethyltoluene + H2O + acceptor
1-(2-methylphenyl)ethanol + reduced acceptor
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-
-
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?
2-ethyltoluene + H2O + ferricenium
? + ferrocene
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3.8% activity compared to ethylbenzene
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-
?
3-ethylphenol + H2O + acceptor
? + reduced acceptor
-
24.3% of the activity with ethylbenzene
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-
?
3-ethylphenol + H2O + ferricenium
3-(1-hydroxyethyl)phenol + ferrocene
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19% activity compared to ethylbenzene
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?
3-ethylphenol + H2O + ferricenium
3-(1-hydroxyethyl)phenol + ferrocenium
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?
3-ethylpyridine + H2O + acceptor
? + reduced acceptor
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16.9% of the activity with ethylbenzene
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-
?
3-ethylpyridine + H2O + ferricenium
? + ferrocene
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16% activity compared to ethylbenzene
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?
3-ethyltoluene + H2O + ferricenium
? + ferrocene
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10% activity compared to ethylbenzene
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?
3-phenylprop-1-ene + H2O + ferricenium
(S)-1-phenylprop-2-en-1-ol + ferrocene
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?
3-phenylprop-1-yne + H2O + ferricenium
(S)-1-phenylprop-2-yn-1-ol + ferrocene
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?
4-ethyl-1,1'-biphenyl + H2O + ferricenium
(S)-1-([1,1'-biphenyl]-4-yl)ethanol + (R)-1-([1,1'-biphenyl]-4-yl)ethanol + ferrocene
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-
-
-
?
4-ethylaniline + H2O + ferricenium
? + ferrocene
-
130% activity compared to ethylbenzene
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?
4-ethylanisole + H2O + ferricenium
1-(4-methoxyphenyl)ethanol + ferrocene
-
22% activity compared to ethylbenzene
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?
4-ethylanisole + H2O + ferricenium
1-(4-methoxyphenyl)ethanol + ferrocenium
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-
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?
4-ethylbiphenyl + H2O + ferricenium
? + ferrocene
-
30% activity compared to ethylbenzene
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-
?
4-ethylphenol + H2O + acceptor
? + reduced acceptor
-
259% of the activity with ethylbenzene
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?
4-ethylphenol + H2O + ferricenium
4-(1-hydroxyethyl)phenol + ferrocene
-
251% activity compared to ethylbenzene
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?
4-ethylphenol + H2O + ferricenium
4-(1-hydroxyethyl)phenol + ferrocenium
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best substrate
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?
4-ethylpyridine + H2O + acceptor
?
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substrate shows 50fold decreased activities of hydroxylation, relative specific activity: 2%
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-
?
4-ethyltoluene + H2O + ferricenium
1-(4-methylphenyl)ethanol + ferrocene
-
28% activity compared to ethylbenzene
-
-
?
4-ethyltoluene + H2O + ferricenium
1-(4-methylphenyl)ethanol + ferrocenium
-
-
-
-
?
4-fluoroethylbenzene + H2O + ferricenium
? + ferrocene
-
15% activity compared to ethylbenzene
-
-
?
4-propylphenol + H2O + ferricenium
4-(1-hydroxypropyl)phenol + ferrocene
-
175% activity compared to ethylbenzene
-
-
?
4-propylphenol + H2O + ferricenium
4-(1-hydroxypropyl)phenol + ferrocenium
-
-
-
-
?
5-methoxy-2,3-dihydro-1H-indene + H2O + ferricenium
(S)-5-methoxy-2,3-dihydro-1H-inden-1-ol + (S)-6-methoxy-2,3-dihydro-1H-inden-1-ol + ferrocene
-
-
-
-
?
allylbenzene + H2O + acceptor
?
-
allylbenzene is hydroxylated 2.8fold faster than ethylbenzene. The introduced CH=CH2 group of the allyl chain may exert both steric and electronic effects on the energetic profile of the reaction. Relative specific activity: 281%
-
-
?
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocenium
-
EBDH catalyzes the oxygen-independent, stereospecific hydroxylation of ethylbenzene to (S)-1-phenylethanol, the direct anaerobic oxidation of a nonactivated hydrocarbon
-
-
?
ethylbenzene + H2O + ferricyanide
(S)-1-phenylethanol + ferrocyanide
-
-
-
-
?
ethylbenzene + H2O + ferrocenium
(S)-1-phenylethanol + ferrocene
-
-
-
-
?
ethylbenzene + H2O + phenazine methosulfate
(S)-1-phenylethanol + reduced phenazine methosulfate
n-propylbenzene + H2O + ferricenium
1-phenylpropanol + ferrocene
-
14% activity compared to ethylbenzene
-
-
?
propylbenzene + H2O + acceptor
? + reduced acceptor
-
15% of the activity with ethylbenzene
-
-
?
propylbenzene + H2O + ferricenium
(S)-1-phenylpropan-1-ol + ferrocene
-
-
-
-
?
rac-1-(4-ethylphenyl)ethanol + H2O + ferricenium
(1S)-1,1'-(benzene-1,4-diyl)diethanol + ferrocene
-
-
-
-
?
1,4-diethylbenzene + H2O + acceptor
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + acceptor
-
-
-
-
?
1,4-diethylbenzene + H2O + acceptor
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + acceptor
-
-
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocene
-
35% activity compared to ethylbenzene
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocene
-
35% activity compared to ethylbenzene
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocenium
-
-
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocenium
-
-
-
-
?
2-ethylaniline + H2O + ferricenium
? + ferrocene
-
92% activity compared to ethylbenzene
-
-
?
2-ethylaniline + H2O + ferricenium
? + ferrocene
-
92% activity compared to ethylbenzene
-
-
?
2-ethylfuran + H2O + ferricenium
1-(2-furyl)ethanol + ferrocene
-
130% activity compared to ethylbenzene
-
-
?
2-ethylfuran + H2O + ferricenium
1-(2-furyl)ethanol + ferrocene
-
130% activity compared to ethylbenzene
-
-
?
2-ethylthiophene + ferricyanide
(S)-1-(2-thienyl)-ethanol + ferrocyanide
-
-
-
-
?
2-ethylthiophene + ferricyanide
(S)-1-(2-thienyl)-ethanol + ferrocyanide
-
-
-
-
?
3-phenyl-1-propene + H2O + ferricyanide
? + ferrocyanide
-
-
-
-
?
3-phenyl-1-propyne + H2O + ferricyanide
? + ferrocyanide
-
-
-
-
?
4-ethylbiphenyl + ferricenium + H2O
1-(1,1'-biphenyl-4-yl)ethanol + ferrocene
-
-
-
-
?
4-ethylbiphenyl + ferricenium + H2O
1-(1,1'-biphenyl-4-yl)ethanol + ferrocene
-
-
-
-
?
4-ethylbiphenyl + H2O + acceptor
1-(1,1'-biphenyl-4-yl)ethanol + reduced acceptor
-
-
-
-
?
4-ethylbiphenyl + H2O + acceptor
1-(1,1'-biphenyl-4-yl)ethanol + reduced acceptor
-
-
-
-
?
4-ethylbiphenyl + H2O + ferricenium
1-(1,1'-biphenyl-4-yl)ethanol + reduced ferrocenium
-
-
-
-
?
4-ethylbiphenyl + H2O + ferricenium
1-(1,1'-biphenyl-4-yl)ethanol + reduced ferrocenium
-
-
-
-
?
4-ethylphenol + H2O + acceptor
4-(1-hydroxyethyl)phenol + acceptor
-
substrate shows 2.5fold increased activities of hydroxylation, relative specific activity: 251%
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
relative specific activity: 100%
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
ir
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
EBDH catalyzes the oxygen-independent, stereospecific hydroxylation of ethylbenzene to (S)-1-phenylethanol
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
ir
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
EBDH catalyzes the oxygen-independent, stereospecific hydroxylation of ethylbenzene to (S)-1-phenylethanol
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
initial step of the degradation pathway from the toxic ethylbenzene to benzoyl-CoA
-
-
?
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocene
-
-
-
-
?
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocene
-
100% activity
-
-
?
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocene
-
-
-
-
?
ethylbenzene + H2O + molybdopterin
(S)-1-phenylethanol + molybdopterin (reduced form)
-
-
-
?
ethylbenzene + H2O + molybdopterin
(S)-1-phenylethanol + molybdopterin (reduced form)
-
-
-
?
ethylbenzene + H2O + phenazine methosulfate
(S)-1-phenylethanol + reduced phenazine methosulfate
-
-
-
-
?
ethylbenzene + H2O + phenazine methosulfate
(S)-1-phenylethanol + reduced phenazine methosulfate
-
-
-
-
?
ethylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylethanol + [Fe(II) (C5H5)2]
-
-
-
ir
ethylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylethanol + [Fe(II) (C5H5)2]
-
-
-
ir
n-propylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylpropanol + [Fe(II) (C5H5)2]
-
-
-
?
n-propylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylpropanol + [Fe(II) (C5H5)2]
-
-
-
?
propylbenzene + H2O + ferricenium
(S)-1-phenylpropanol + ferrocene
-
-
-
-
?
propylbenzene + H2O + ferricenium
(S)-1-phenylpropanol + ferrocene
-
-
-
-
?
additional information
?
-
-
EBDH is a bacterial molybdopterin enzyme capable of stereospecific anaerobic hydroxylation of alkylaromatic compounds to secondary alcohols
-
-
?
additional information
?
-
-
no activity with ethylidenecyclohexane, n-propylbenzene and 2-ethylpyrazine
-
-
?
additional information
?
-
-
no activity with ethylidenecyclohexane, n-propylbenzene and 2-ethylpyrazine
-
-
?
additional information
?
-
-
substrate specificity, product identification by GC- and LC-MS, overview
-
-
?
additional information
?
-
-
substrate specificity, product identification by GC- and LC-MS, overview
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
EBDH is a bacterial molybdopterin enzyme capable of stereospecific anaerobic hydroxylation of alkylaromatic compounds to secondary alcohols
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
ir
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
anaerobic degradation of ethylbenzene in bacteria
-
ir
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
-
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
-
initial step of the degradation pathway from the toxic ethylbenzene to benzoyl-CoA
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
bis(molybdopterin guanine dinucleotide)molybdenum
-
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Molybdenum
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.