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Information on EC 1.14.13.1 - salicylate 1-monooxygenase
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1.14.13.1 salicylate 1-monooxygenaseIUBMB Comments
A flavoprotein (FAD).
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Word Map
- 1.14.13.1
- catechol
- naphthalene
-
1,2-dioxygenase
- gentisate
-
sa-mediated
-
naphthalene-degrading
-
sa-deficient
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sa-independent
- analysis
- diagnostics
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
salicylate hydroxylase, salicylate 1-monooxygenase, sa hydroxylase, salicylate 1-hydroxylase, salicylate monooxygenase, fgshy1, fgsg_03657, saloh, fgshyc, salicylic acid hydroxylase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FAD_binding_3 domain-containing protein
FgShy1
FgShyC
flavin-dependent monooxygenase salicylate hydroxylase
NahG
NahU
NRRL3_9723
oxygenase, salicylate 1-mono-
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-
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-
SA hydroxylase
salA
SALH
salicylate 1-hydroxylase
Salicylate 1-monooxygenase
salicylate hydroxylase
salicylate hydroxylase (decarboxylating)
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salicylate monooxygenase
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-
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salicylate, NADH: oxygen oxidoreductase
salicylate, NADH: oxygen oxidoreductase (1-hydroxylating, decarboxylating)
salicylic acid hydroxylase
salicylic hydroxylase
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-
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Shy1
ShyA
ShyC
salicylate 1-hydroxylase
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salicylate, NADH: oxygen oxidoreductase (1-hydroxylating, decarboxylating)
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salicylate, NADH: oxygen oxidoreductase (1-hydroxylating, decarboxylating)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
salicylate + NADH + H+ + O2 = catechol + NAD+ + H2O + CO2
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-
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salicylate + NADH + H+ + O2 = catechol + NAD+ + H2O + CO2
analysis of the reaction mechanism of SALH using combined quantum mechanical/molecular mechanical (QM/MM) calculations, overview. The whole enzymatic reaction contains two parts: the hydroxylation and decarboxylation. The deprotonated substrate is the active form, whereas the neutral form of salicylate corresponds to very a high energy barrier (39.8 kcal/mol) for the hydroxylation process, which is in line with the experimental result that the optimum pH is 7.6. The calculated results with the deprotonated substrate indicate that the hydroxylation and decarboxylation occur in a stepwise manner and the decarboxylation process is calculated to be the rate-limiting step with an energy barrier of 14.5 kal/mol. The catalytic reaction is highly exothermic. It proceeds via a C4a-hydorperoxyflavin
salicylate + NADH + H+ + O2 = catechol + NAD+ + H2O + CO2
oxidative decarboxylation of salicylate catalyzed by NahG, catalytic mechanism, detailed overview. The salicylate carboxyl group lies near a hydrophobic region that aids decarboxylation. A conserved histidine residue is proposed to assist the reaction by general base/general acid catalysis
salicylate + NADH + H+ + O2 = catechol + NAD+ + H2O + CO2
oxidative decarboxylation of salicylate catalyzed by NahG, catalytic mechanism, detailed overview. The salicylate carboxyl group lies near a hydrophobic region that aids decarboxylation. A conserved histidine residue is proposed to assist the reaction by general base/general acid catalysis
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salicylate + NADH + H+ + O2 = catechol + NAD+ + H2O + CO2
analysis of the reaction mechanism of SALH using combined quantum mechanical/molecular mechanical (QM/MM) calculations, overview. The whole enzymatic reaction contains two parts: the hydroxylation and decarboxylation. The deprotonated substrate is the active form, whereas the neutral form of salicylate corresponds to very a high energy barrier (39.8 kcal/mol) for the hydroxylation process, which is in line with the experimental result that the optimum pH is 7.6. The calculated results with the deprotonated substrate indicate that the hydroxylation and decarboxylation occur in a stepwise manner and the decarboxylation process is calculated to be the rate-limiting step with an energy barrier of 14.5 kal/mol. The catalytic reaction is highly exothermic. It proceeds via a C4a-hydorperoxyflavin
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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oxidative decarboxylation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
salicylate,NADH:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
A flavoprotein (FAD).
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CAS REGISTRY NUMBER
COMMENTARY
9059-28-3
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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
1-hydroxy-2-naphthoate + NADH + 2 H+ + O2
?
-
137% of the activity with salicylate
-
-
?
1-hydroxy-2-naphthoate + NADH + O2
1,2-dihydroxynaphthalene + CO2 + H2O + NAD+
-
-
-
-
?
2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurzitane + NADH
NO2- + N2O + formate + NH4+
-
the enzyme catalyzes two oxygen-sensitive single-electron transfer steps necessary to release two nitrite ions from 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurzitane and this is followed by the secondary decomposition of this energetic chemical
N2O is abiotically produced from NO2-NH2
-
?
2,4-dihydroxybenzoate + NAD(P)H + O2
benzene-1,2,4-triol + CO2 + H2O + NAD(P)+
-
-
-
?
2,4-dihydroxybenzoate + NADH + 2 H+ + O2
1,2,4-trihydroxybenzene + NAD+ + H2O + CO2
-
91% of the activity with salicylate
-
-
?
2,4-dihydroxybenzoate + NADPH + H+ + O2
benzene-1,2,4-triol + NAD+ + H2O + CO2
-
-
-
-
r
2,5-dihydroxybenzoic acid + NADH + H+ + O2
2,5-dihydroxyphenol + NAD+ + H2O + CO2
146% activity compared to salicylate
-
-
?
2,6-dihydroxybenzoate + NADH + 2 H+ + O2
1,2,3-trihydroxybenzene + NAD+ + H2O + CO2
-
70% of the activity with salicylate
-
-
?
2-hydroxy-1-naphthoate + NADH + 2 H+ + O2
?
-
160% of the activity with salicylate
-
-
?
3-chlorosalicylate + NADH + H+ + O2
3-chlorocatechol + NAD+ + H2O + CO2
-
-
-
?
3-methylsalicylate + NADH + H+ + O2
3-methylcatechol + NAD+ + H2O + CO2
-
-
-
?
4-(3-benzothiazol-2-yl-4-cyano-2-oxo-2H-chromen-7-yloxymethyl)-2-hydroxy-benzoic acid + O2 + NADH + 2 H+
?
-
i.e. SHLF, two-step synthesis of a long-wavelength latent fluorogenic substrate SHLF. In the presence of NADH and under aerobic conditions, SHL catalyzes the decarboxylative hydroxylation of SHLF followed by a quinonemethide-type rearrangement reaction concomitant with the ejection of a fluorescence coumarin 2, which is spontaneous and irreversible at physiological temperatures in aqueous media. The fluorescence signal generated by this process is specific and, in the near red spectral region with an emission maximum at 595 nm, is suppressed by salicylic acid
-
-
?
4-chlorosalicylate + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O + CO2
-
-
-
?
4-chlorosalicylate + NADH + O2
4-chlorocatechol + NAD+ + H2O + CO2
-
-
-
-
?
4-methylsalicylate + NADH + O2
1,2-dihydroxy-4-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-aminosalicylate + NADH + O2
5-aminocatechol + CO2 + NAD+ + H2O
-
-
-
-
?
5-chlorosalicylate + NADH + 2 H+ + O2
4-chlorocatechol + NAD+ + H2O + CO2
-
46% of the activity with salicylate
-
-
?
5-chlorosalicylate + NADH + H+ + O2
5-chlorocatechol + NAD+ + H2O + CO2
-
-
-
?
5-fluorosalicylate + NADH + O2
1,2-dihydroxy-5-fluorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methoxysalicylate + NADH + O2
1,2-dihydroxy-5-methoxybenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + 2 H+ + O2
4-methylcatechol + NAD+ + H2O + CO2
-
68.5% of the activity with salicylate
-
-
?
5-nitrosalicylate + NADH + 2 H+ + O2
4-nitrocatechol + NAD+ + H2O + CO2
-
32% of the activity with salicylate
-
-
?
anthranilate + NADH + 2 H+ + O2
2-aminophenol + NAD+ + H2O + CO2
-
67% of the activity with salicylate
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-
?
gentisate + NADH + 2 H+ + O2
hydroxyquinol + NAD+ + H2O + CO2
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93% activity compared to salicylate
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-
?
m-hydroxybenzoate + NADH + O2
1,3-dihydroxybenzene + CO2 + NAD+ + H2O
-
6% of the reaction with salicylate
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-
?
1-hydroxy-2-naphthoate + NADH + H+ + O2
?
-
25% activity compared to salicylate
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-
?
1-hydroxy-2-naphthoate + NADH + H+ + O2
?
-
25% activity compared to salicylate
-
-
?
1-hydroxy-2-naphthoate + NADH + H+ + O2
?
-
83% activity compared to salicylate
-
-
?
1-hydroxy-2-naphthoate + NADH + H+ + O2
?
-
83% activity compared to salicylate
-
-
?
2,3-dihydroxybenzoate + NADH + 2 H+ + O2
pyrogallol + NAD+ + H2O + CO2
-
82% activity compared to salicylate
-
-
?
2,3-dihydroxybenzoate + NADH + 2 H+ + O2
pyrogallol + NAD+ + H2O + CO2
-
82% activity compared to salicylate
-
-
?
2,3-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
?
2,3-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
2,3-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
2,3-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
?
2,3-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
2,5-dihydroxybenzoate + NADH + O2
benzene-1,2,5-triol + CO2 + H2O + NAD+
-
or NADPH
-
?
2,5-dihydroxybenzoate + NADH + O2
benzene-1,2,5-triol + CO2 + H2O + NAD+
-
-
-
-
?
2,5-dihydroxybenzoate + NADH + O2
benzene-1,2,5-triol + CO2 + H2O + NAD+
-
-
-
-
?
2,5-dihydroxybenzoate + NADH + O2
benzene-1,2,5-triol + CO2 + H2O + NAD+
-
-
-
-
?
2,6-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
?
2,6-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
2,6-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
2,6-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
?
2,6-dihydroxybenzoate + NADH + O2
pyrogallol + CO2 + H2O + NAD+
-
-
-
-
?
3-aminosalicylate + NADH + H+ + O2
3-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
11% activity compared to salicylate
-
-
?
3-aminosalicylate + NADH + H+ + O2
3-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
11% activity compared to salicylate
-
-
?
3-aminosalicylate + NADH + H+ + O2
3-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
62% activity compared to salicylate
-
-
?
3-aminosalicylate + NADH + H+ + O2
3-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
62% activity compared to salicylate
-
-
?
3-chlorosalicylate + NADH + H+ + O2
3-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
15% activity compared to salicylate
-
-
?
3-chlorosalicylate + NADH + H+ + O2
3-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
15% activity compared to salicylate
-
-
?
3-chlorosalicylate + NADH + H+ + O2
3-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
23% activity compared to salicylate
-
-
?
3-chlorosalicylate + NADH + H+ + O2
3-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
23% activity compared to salicylate
-
-
?
3-methylsalicylate + NADH + 2 H+ + O2
3-methylcatechol + NAD+ + H2O + CO2
-
-
-
r
3-methylsalicylate + NADH + 2 H+ + O2
3-methylcatechol + NAD+ + H2O + CO2
-
-
-
r
3-methylsalicylate + NADH + 2 H+ + O2
3-methylcatechol + NAD+ + H2O + CO2
-
76% of the activity with salicylate
-
-
?
3-methylsalicylate + NADH + H+ + O2
3-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
47% activity compared to salicylate
-
-
?
3-methylsalicylate + NADH + H+ + O2
3-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
86% activity compared to salicylate
-
-
?
3-methylsalicylate + NADH + O2
1,2-dihydroxy-3-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
3-methylsalicylate + NADH + O2
1,2-dihydroxy-3-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
3-methylsalicylate + NADH + O2
1,2-dihydroxy-3-methylbenzene + NAD+ + H2O + CO2
-
-
-
-
?
3-methylsalicylate + NADH + O2
1,2-dihydroxy-3-methylbenzene + NAD+ + H2O + CO2
-
-
-
-
?
4-aminosalicylate + NADH + 2 H+ + O2
4-aminocatechol + NAD+ + H2O + CO2
-
72% activity compared to salicylate
-
-
?
4-aminosalicylate + NADH + 2 H+ + O2
4-aminocatechol + NAD+ + H2O + CO2
-
72% activity compared to salicylate
-
-
?
4-aminosalicylate + NADH + H+ + O2
4-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
94% activity compared to salicylate
-
-
?
4-aminosalicylate + NADH + H+ + O2
4-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
130% activity compared to salicylate
-
-
?
4-aminosalicylate + NADH + O2
4-aminocatechol + CO2 + NAD+ + H2O
-
-
-
-
?
4-aminosalicylate + NADH + O2
4-aminocatechol + CO2 + NAD+ + H2O
-
-
-
-
?
4-aminosalicylate + NADH + O2
4-aminocatechol + CO2 + NAD+ + H2O
-
-
-
-
?
4-chlorosalicylate + NADH + H+ + O2
4-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
43% activity compared to salicylate
-
-
?
4-chlorosalicylate + NADH + H+ + O2
4-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
78% activity compared to salicylate
-
-
?
4-chlorosalicylate + NADH + O2
1,2-dihydroxy-4-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
4-chlorosalicylate + NADH + O2
1,2-dihydroxy-4-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
4-chlorosalicylate + NADH + O2
1,2-dihydroxy-4-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
4-chlorosalicylate + NADH + O2
1,2-dihydroxy-4-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
4-methylsalicylate + NADH + 2 H+ + O2
4-methylcatechol + NAD+ + H2O + CO2
-
-
-
?
4-methylsalicylate + NADH + 2 H+ + O2
4-methylcatechol + NAD+ + H2O + CO2
-
108% of the activity with salicylate
-
-
?
4-methylsalicylate + NADH + H+ + O2
4-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
166% activity compared to salicylate
-
-
?
4-methylsalicylate + NADH + H+ + O2
4-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
164% activity compared to salicylate
-
-
?
5-aminosalicylate + NADH + 2 H+ + O2
5-aminocatechol + NAD+ + H2O + CO2
-
-
-
r
5-aminosalicylate + NADH + 2 H+ + O2
5-aminocatechol + NAD+ + H2O + CO2
-
-
-
r
5-aminosalicylate + NADH + H+ + O2
5-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
80% activity compared to salicylate
-
-
?
5-aminosalicylate + NADH + H+ + O2
5-aminobenzene-1,2-diol + NAD+ + H2O + CO2
-
50% activity compared to salicylate
-
-
?
5-chlorosalicylate + NADH + H+ + O2
5-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
14% activity compared to salicylate
-
-
?
5-chlorosalicylate + NADH + H+ + O2
5-chlorobenzene-1,2-diol + NAD+ + H2O + CO2
-
18% activity compared to salicylate
-
-
?
5-chlorosalicylate + NADH + O2
1,2-dihydroxy-5-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-chlorosalicylate + NADH + O2
1,2-dihydroxy-5-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-chlorosalicylate + NADH + O2
1,2-dihydroxy-5-chlorobenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-chlorosalicylate + NADH + O2
1,2-dihydroxy-5-chlorobenzene + NAD+ + H2O + CO2
-
-
-
-
?
5-chlorosalicylate + NADH + O2
1,2-dihydroxy-5-chlorobenzene + NAD+ + H2O + CO2
-
-
-
-
?
5-hydroxysalicylate + NADH + H+ + O2
2,5-dihydroxyphenol + NAD+ + H2O + CO2
-
132% activity compared to salicylate
-
-
?
5-hydroxysalicylate + NADH + H+ + O2
2,5-dihydroxyphenol + NAD+ + H2O + CO2
-
84% activity compared to salicylate
-
-
?
5-methylsalicylate + NADH + 2 H+ + O2
5-methylcatechol + NAD+ + H2O + CO2
-
-
-
r
5-methylsalicylate + NADH + 2 H+ + O2
5-methylcatechol + NAD+ + H2O + CO2
-
-
-
r
5-methylsalicylate + NADH + 2 H+ + O2
5-methylcatechol + NAD+ + H2O + CO2
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
1,2-dihydroxy-5-methylbenzene + CO2 + NAD+ + H2O
-
-
-
-
?
5-methylsalicylate + NADH + H+ + O2
4-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
81% activity compared to salicylate
-
-
?
5-methylsalicylate + NADH + H+ + O2
4-methylbenzene-1,2-diol + NAD+ + H2O + CO2
-
40% activity compared to salicylate
-
-
?
p-aminosalicylate + NADH + O2
1,2-dihydroxy-4-aminobenzene + NAD+ + CO2 + H2O
-
-
-
-
?
p-aminosalicylate + NADH + O2
1,2-dihydroxy-4-aminobenzene + NAD+ + CO2 + H2O
-
-
-
-
?
salicylate + NADH + 2 H+ + O2
cat