Ligand salicylic acid

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Basic Ligand Information

Molecular Structure

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

Related pathways

KEGG

Bile secretion, Biosynthesis of phenylpropanoids, Biosynthesis of plant hormones, Biosynthesis of secondary metabolites, Biosynthesis of siderophore group nonribosomal peptides

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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S-adenosyl-L-methionine + salicylate = methyl salicylate + S-adenosyl-L-homocysteine

756883, 757709, 756767, 757953, 757984

2.1.1.274

2 entries

2.4.1.177

UDP-glucose + salicylate = UDP + salicoyl beta-D-glucoside

759563

4.1.1.91

salicylate = phenol + CO2

In Vivo Product in Enzyme-catalyzed Reactions (12 results)

acetylsalicylic acid + H2O = acetate + salicylate

3.1.2.23

2-hydroxybenzoyl-CoA + H2O = 2-hydroxybenzoate + CoA

3.7.1.8

2 entries

4.2.99.21

isochorismate = salicylate + pyruvate

6za5, 3D-view

Substrate in Enzyme-catalyzed Reactions (41 results)

salicylate + O2 = ?

salicylic acid + NAD(P)H + O2 + H2O = ?

659034

1.14.12.13

2-hydroxybenzoate + NADH + O2 = catechol + ? + NAD+ + CO2

2-hydroxybenzoic acid + NADPH + H+ + O2 = ? + NADP+ + H2O

2-hydroxybenzoate + [reduced NADPH-hemoprotein reductase] + O2 = 2,4-dihydroxybenzoate + [oxidized NADPH-hemoprotein reductase] + H2O

440261

1.2.1.30

salicylic acid + NADPH + ATP = salicyl aldehyde + NADP+ + AMP + H2O

UDP-glucose + salicylic acid = UDP + salicylic acid 7-O-beta-D-glucoside

663180

2.4.1.177

UDP-glucose + salicylate = UDP + salicoyl beta-D-glucoside

759563

2.4.1.35

UDPglucose + salicylic acid = UDP + 2-(beta-D-glucopyranosyloxy)benzoate

489108

4.1.1.46

salicylic acid = phenol + CO2

747588

4.1.1.91

salicylate = phenol + CO2

707400

6jqx, 3D-view

6.2.1.17

ATP + salicylate + CoA = AMP + diphosphate + salicyl-CoA

660

6.2.1.25

ATP + 2-hydroxybenzoate + CoA = AMP + diphosphate + 2-hydroxybenzoyl-CoA

ATP + salicylic acid + phosphopantetheinylated EntB = arylated EntB + AMP + diphosphate

726950

Product in Enzyme-catalyzed Reactions (97 results)

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1.1.1.274

2-carboxybenzaldehyde + NADPH = 2-hydroxybenzoate + NADP+

2-hydroxybenzaldehyde + NAD+ + H2O = 2-hydroxybenzoate + NADH + H+

salicylaldehyde + NAD+ + H2O = salicylate + NADH + 2 H+

1.2.1.7

salicylaldehyde + NADP+ + H2O = salicylic acid + NADPH

1.2.3.1

2 entries

1.2.3.9

salicylaldehyde + O2 + H2O = salicylic acid + H2O2

1.2.7.5

salicylaldehyde + H2O + oxidized benzyl viologen = salicylic acid + H+ + reduced benzyl viologen

2-methoxybenzoate + a [Co(I) methoxylated-aromatic-compound-specific corrinoid protein] = a [methyl-Co(III) methoxylated-aromatic-compound-specific corrinoid protein] + 2-hydroxybenzoate

3.1.1.1

13 entries

3.1.1.20

methyl salicylate + H2O = methanol + salicylate

3.1.1.55

10 entries

3.1.1.8

acetylsalicylic acid + H2O = acetate + salicylate

3.1.1.84

ethyl 2-hydroxybenzoate + H2O = ethanol + 2-hydroxybenzoate

3.1.2.20

2 entries

3.1.2.23

2-hydroxybenzoyl-CoA + H2O = 2-hydroxybenzoate + CoA

3.1.2.28

salicylyl-CoA + H2O = CoA + salicylate

3.1.3.1

o-carboxyphenyl phosphate + H2O = o-carboxyphenol + phosphate

3.1.3.2

o-carboxyphenyl phosphoric acid + H2O = o-carboxyphenol + phosphate

3.1.6.1

2-carboxyphenyl sulfate + H2O = 2-carboxyphenol + sulfate

o-hydroxy-benzonitrile + H2O = o-hydroxy-benzoic acid + NH3

3.7.1.8

3 entries

3.9.1.1

o-carboxyphenylphosphate + H2O = salicylic acid + phosphate + CO2

4.2.99.21

isochorismate = salicylate + pyruvate

6za5, 3D-view

Activator in Enzyme-catalyzed Reactions (25 results)

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1.1.1.267

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

activates best at 20 mM, pH changes

0.25 mM

2 mM, induction of RdRp gene expression

694100

3.1.1.2

induces enzyme expression in the liver and stimulates enzymatic activity in blood plasma

693517

3.1.1.4

enhanced enzyme penetration, activation above the normal cutoff pressure of PLA2

rapid activation

44.6% increase of enzyme activity after treatment with 1 mmol/l salicylic acid for 5 h

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

694663

7.1.1.9

produces a slight and transient increase in transcript levels of COX19

694694

7.6.2.1

stimulates

246838

Inhibitor in Enzyme-catalyzed Reactions (94 results)

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1.1.1.1

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

isoform LOX2 exhibits 96% residual activity at 2.8 mM

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

661547

2.7.2.3

i.e. 2-hydroxybenzoate

642248

2.7.8.2

250 ng/microl, 38% inhibition of enzyme activity in microsomal fraction of mesangial cells

competitive with respect to 1-naphththalenemethanol

644831

3.1.1.1

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

competitive

inhibition below the normal cutoff pressure of PLA2

133911

3.1.3.2

competitive inhibition of hydrolysis of p-nitrophenyl phosphate, no effect on hydrolysis of 3'-AMP

complete inhibition at 10 mM, 61.4% inhibition at 1 mM

50% inhibition at 1.65 mM

670640

3.4.22.15

and its m-analogs and p-analogs

97% inhibition at 1 mM

733611

3.5.1.98

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

682471

6za5, 3D-view

5.6.2.2

salicylic acid suppresses the ATPase and decatenation but not relaxation activity of the enzyme

751612

6.2.1.17

inhibition of propanoyl-CoA formation in solubilized mitochondria

competitive

0.5 mM, 45% inhibition

675654

3D Structure of Enzyme-Ligand-Complex (PDB) (218 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (37 results)

4.17

0.0163

pH 7.5, 30°C

0.034

pH 5.5, 40°C

707400

6.2.1.25

0.63

pH 8.0, 31°C, recombinant wild-type enzyme

0.8

pH 7.8, 25°C, recombinant EntE

726950

K_M Value (50 results)

0.28

0.167

0.0068

pH 7.5, 30°C

1.08

pH 5.5, 40°C

707400

6.2.1.25

0.0016

pH 8.0, 31°C, recombinant wild-type enzyme

0.07

pH 7.8, 25°C, recombinant EntE

726950

K_i Value (24 results)

0.0078

0.115

0.75

0.1905

5.2

0.81

pH 8.5, 25°C

2.3

2.2

3.1

0.067

pH 7, 37°C

0.0196

pH 8.5, 37°C

0.016

0.0183

pH 8.0, 37°C

692840

IC₅₀ Value (7 results)

0.77

3.6

4.3

0.15

pH 7.4, 37°C, versus 4-nitrophenol

673189

2.8.2.4

0.91

pH 6.5, 37°C, versus beta-estradiol

673189

4.2.1.1

2 entries

References & Links

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Show Reference (246 entries)

Links to other databases for salicylic acid

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Ligand salicylic acid

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

In Vivo Product in Enzyme-catalyzed Reactions (12 results)

Substrate in Enzyme-catalyzed Reactions (41 results)

Product in Enzyme-catalyzed Reactions (97 results)

Activator in Enzyme-catalyzed Reactions (25 results)

Inhibitor in Enzyme-catalyzed Reactions (94 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (218 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (37 results)

KM Value (50 results)

Ki Value (24 results)

IC50 Value (7 results)

References & Links

Literature References (246)

Links to other databases for salicylic acid

k_cat Value (Turnover Number) (37 results)

K_M Value (50 results)

K_i Value (24 results)

IC₅₀ Value (7 results)