Ligand salicylic acid

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Basic Ligand Information

Molecular Structure
Picture of salicylic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O3
salicylic acid
YGSDEFSMJLZEOE-UHFFFAOYSA-N
Synonyms:
2-Carboxyphenol, 2-Hydroxybenzoate, 2-hydroxybenzoic acid, o-carboxyphenol, o-hydroxy-benzoic acid, o-hydroxybenzoate, o-hydroxybenzoic acid, salicylate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + salicylate = S-adenosyl-L-homocysteine + methyl salicylate
show the reaction diagram
-
salicylate = phenol + CO2
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetylsalicylic acid + H2O = acetate + salicylate
show the reaction diagram
-
-
2-hydroxybenzoyl-CoA + H2O = 2-hydroxybenzoate + CoA
show the reaction diagram
-
-
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O = 2-oxopent-4-enoate + salicylate + H+
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
salicylate + O2 = ?
show the reaction diagram
-
salicylic acid + NAD(P)H + O2 + H2O = ?
show the reaction diagram
-
2-hydroxybenzoate + NADH + O2 = catechol + ? + NAD+ + CO2
show the reaction diagram
-
2-hydroxybenzoic acid + NADPH + H+ + O2 = ? + NADP+ + H2O
show the reaction diagram
-
2-hydroxybenzoate + [reduced NADPH-hemoprotein reductase] + O2 = 2,4-dihydroxybenzoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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salicylic acid + NADPH + ATP = salicyl aldehyde + NADP+ + AMP + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + salicylate = S-adenosyl-L-homocysteine + methyl salicylate
show the reaction diagram
-
UDP-glucose + salicylic acid = UDP + salicylic acid 7-O-beta-D-glucoside
show the reaction diagram
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UDPglucose + salicylic acid = UDP + 2-(beta-D-glucopyranosyloxy)benzoate
show the reaction diagram
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ATP + 2-hydroxybenzoic acid = diphosphate + (2-hydroxybenzoyl)adenylate
show the reaction diagram
-
salicylic acid = phenol + CO2
show the reaction diagram
-
salicylate = phenol + CO2
show the reaction diagram
-
ATP + salicylate + CoA = AMP + diphosphate + salicyl-CoA
show the reaction diagram
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ATP + 2-hydroxybenzoate + CoA = AMP + diphosphate + 2-hydroxybenzoyl-CoA
show the reaction diagram
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ATP + salicylic acid + phosphopantetheinylated EntB = arylated EntB + AMP + diphosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (107 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-carboxybenzaldehyde + NADPH = 2-hydroxybenzoate + NADP+
show the reaction diagram
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-
2-hydroxybenzaldehyde + NAD+ + H2O = 2-hydroxybenzoate + NADH + H+
show the reaction diagram
-
-
salicylaldehyde + NAD+ + H2O = salicylate + NADH + 2 H+
show the reaction diagram
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-
salicylaldehyde + NADP+ + H2O = salicylic acid + NADPH
show the reaction diagram
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-
salicylaldehyde + O2 + H2O = salicylic acid + H2O2
show the reaction diagram
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-
salicylaldehyde + H2O + oxidized benzyl viologen = salicylic acid + H+ + reduced benzyl viologen
show the reaction diagram
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methyl salicylate + H2O = methanol + salicylate
show the reaction diagram
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-
acetylsalicylic acid + H2O = acetate + salicylate
show the reaction diagram
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ethyl 2-hydroxybenzoate + H2O = ethanol + 2-hydroxybenzoate
show the reaction diagram
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-
2-hydroxybenzoyl-CoA + H2O = 2-hydroxybenzoate + CoA
show the reaction diagram
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-
salicylyl-CoA + H2O = CoA + salicylate
show the reaction diagram
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o-carboxyphenyl phosphate + H2O = o-carboxyphenol + phosphate
show the reaction diagram
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o-carboxyphenyl phosphoric acid + H2O = o-carboxyphenol + phosphate
show the reaction diagram
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2-carboxyphenyl sulfate + H2O = 2-carboxyphenol + sulfate
show the reaction diagram
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isochorismate + H2O = salicylate + pyruvate
show the reaction diagram
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-
o-hydroxy-benzonitrile + H2O = o-hydroxy-benzoic acid + NH3
show the reaction diagram
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-
o-carboxyphenylphosphate + H2O = salicylic acid + phosphate + CO2
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
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
-
produces a slight and transient increase in transcript levels of COX19
-
activates best at 20 mM, pH changes
-
0.25 mM
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2 mM, induction of RdRp gene expression
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induces enzyme expression in the liver and stimulates enzymatic activity in blood plasma
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enhanced enzyme penetration, activation above the normal cutoff pressure of PLA2
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rapid activation
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44.6% increase of enzyme activity after treatment with 1 mmol/l salicylic acid for 5 h
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activates phenylalanine ammonia-lyase in grape berry in response to high temperature stress, it also induces the accumulation of PAL mRNA and the synthesis of new PAL protein, in addition to increasing the enzyme activity, under high temperature stress
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stimulates
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Inhibitor in Enzyme-catalyzed Reactions (93 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.5 mM, 12% inhibition of hepatic allotype ADH1B*1/*1 activity, 31% inhibition of hepatic allotype ADH1B*2/*2 activity
-
at pH 9.9
-
non-competitive
-
46.0% inhibition at 0.015 mM, active site binding structure
-
competitive with respect to 2-oxoglutarate and ascorbate, noncompetitive with respect to Fe2+
-
over 70% inhibition at 10 mM
-
1 mM, 62% inhibition
-
10% inhibition
-
weak inhibition of IKK-2
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i.e. 2-hydroxybenzoate
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250 ng/microl, 38% inhibition of enzyme activity in microsomal fraction of mesangial cells
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competitive with respect to 1-napththalenemethanol
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of 14 recombinant methyl esterase proteins tested, five show preference for methyl salicylate as a substrate and display salicylate inhibition of methyl salicylate esterase activity in vitro, i.e. AtMES1, -2, -4, -7, and -9
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competitive
-
inhibition below the normal cutoff pressure of PLA2
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competitive inhibition of hydrolysis of p-nitrophenyl phosphate, no effect on hydrolysis of 3'-AMP
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complete inhibition at 10 mM, 61.4% inhibition at 1 mM
-
50% inhibition at 1.65 mM
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and its m-analogs and p-analogs
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97% inhibition at 1 mM
-
92% residual activity at 0.5 mM
-
causes inactivation by dissociation of the apoenzyme into its subunits
-
PAL activity decreases with prolonged exposure to 0.25 mM salicylic acid indicating its inhibition
-
treatment of plants suppresses the enhancement of enzyme expression by O3
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salicylic acid suppresses the ATPase and decatenation but not relaxation activity of the enzyme
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inhibition of propanoyl-CoA formation in solubilized mitochondria
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competitive
-
0.5 mM, 45% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (31 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.6
-
pH not specified in the publication, 25C
4.17
-
-
2.5
-
pH 9.0, 37C
0.034
-
pH 5.5, 40C
0.63
-
pH 8.0, 31C, recombinant wild-type enzyme
0.8
-
pH 7.8, 25C, recombinant EntE

KM Value (32 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.1071
-
in 50 mM MES buffer (pH 6.4), at 22C
0.28
-
-
0.167
-
-
0.091
-
pH 9.0, 37C
1.08
-
pH 5.5, 40C
0.0016
-
pH 8.0, 31C, recombinant wild-type enzyme
0.07
-
pH 7.8, 25C, recombinant EntE

Ki Value (23 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0078
-
-
0.115
0.75
-
0.1905
-
-
5.2
-
-
2.3
-
-
2.2
-
-
3.1
-
-
0.067
-
pH 7, 37C
0.0196
-
pH 8.5, 37C
0.016
-
-
0.0183
-
pH 8.0, 37C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.77
-
;
3.6
-
-
4.3
-
-
0.15
-
pH 7.4, 37C, versus 4-nitrophenol
0.91
-
pH 6.5, 37C, versus beta-estradiol

References & Links

Links to other databases for salicylic acid

ChEBI
PubChem
ChEBI
PubChem