Ligand syringic acid

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Basic Ligand Information

Molecular Structure
Picture of syringic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H10O5
syringic acid
JMSVCTWVEWCHDZ-UHFFFAOYSA-N
Synonyms:
3,5-Dimethoxy-4-hydroxy-benzoate, 3,5-Dimethoxy-4-hydroxybenzoate, 3,5-dimethoxy 4-hydroxybenzoic acid, 4-hydroxy-3,5-dimethoxybenzoic acid, 4-hydroxy-3,5-dimethoxy benzoic acid, syringate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
syringate + NADH + O2 = ?
show the reaction diagram
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syringate + tetrahydrofolate = 3-O-methylgallate + 5-methyltetrahydrofolate
show the reaction diagram
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UDP-glucose + syringate = UDP + syringoyl beta-D-glucoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
syringaldehyde + NAD+ + H2O = syringate + NADH + H+
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
syringic acid + H2O2 = ?
show the reaction diagram
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syringic acid + O2 = ?
show the reaction diagram
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S-adenosyl-L-methionine + 4-hydroxy-3,5-dimethoxybenzoic acid = S-adenosyl-L-homocysteine + 3,4,5-trimethoxybenzoic acid
show the reaction diagram
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UDP-glucose + syringic acid = UDP + 4-O-glucosyl syringic acid
show the reaction diagram
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UDP-alpha-D-glucose + syringic acid = UDP + 1-O-syringoyl-beta-D-glucose
show the reaction diagram
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UDP-glucose + syringate = UDP + syringoyl beta-D-glucoside
show the reaction diagram
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UDP-glucose + syringic acid = UDP + syringoyl 3-O-beta-D-glucoside
show the reaction diagram
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3,5-Dimethoxy-4-hydroxybenzoate = 1,3-Dimethoxy-2-hydroxybenzene + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxy-3,5-dimethoxybenzaldehyde + NAD+ + H2O = 4-hydroxy-3,5-dimethoxybenzoic acid + NADH + H+
show the reaction diagram
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syringaldehyde + O2 + H2O = syringic acid + H2O2
show the reaction diagram
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3,5-Dimethoxy-4-hydroxy-benzaldehyde + carbamoyl methyl viologen = 3,5-Dimethoxy-4-hydroxy-benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
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1-O-syringoyl-beta-D-glucose + H2O = 4-hydroxy-3,5-dimethoxy benzoic acid + beta-D-glucose
show the reaction diagram
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N-syringoylglycine + H2O = syringate + glycine
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
111.4% activity at 2.5 mM with cellobioside as substrate
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Inhibitor in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
uncompetitive inhibition
-
48% inhibition at 5 mM, mixed-type inhibition in vitro
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syringic acid
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inhibition of P-PST and M-PST
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inhibitory in micromolar concentrations
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95.2% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside as substrate
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (3 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
10.1
-
pH 4.5, 25°C

KM Value (8 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.028
-
-

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0214
-
-
0.0214
-
at 25°C
1.94
-
pH 6.8, 37°C
0.00171
-
pH 8.5, 37°C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.4
-
-
0.4
-
at 25°C
4.16
-
pH not specified in the publication, temperature not specified in the publication, MAO-A
0.00181
-
pH 8.5, 37°C
0.037
-
pH 6.5, 37°C

References & Links

Links to other databases for syringic acid

ChEBI
PubChem
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PubChem