Ligand tyramine

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Basic Ligand Information

Molecular Structure
Picture of tyramine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H11NO
tyramine
DZGWFCGJZKJUFP-UHFFFAOYSA-N
Synonyms:
4-(2-aminoethyl)phenol, 4-hydroxy-beta-phenylethylamine, 4-hydroxyphenylethylamine, 4-tyramine, beta,beta-dideuterated tyramine, p-tyramine


Show all pahtways known for Show all BRENDA pathways known for tyramine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
tyramine + NADPH + O2 = tyramine N-oxide + NADP+ + H2O
show the reaction diagram
-
tyramine + H2O + O2 = 4-hydroxyphenylethanal + NH3 + H2O2
show the reaction diagram
-
feruloyl-CoA + tyramine = CoA + feruloyltyramine
show the reaction diagram
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ATP + tyramine + L-glutamate = ADP + phosphate + gamma-glutamyltyramine
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-Tyrosine = Tyramine + CO2
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-(2-aminoethyl)phenol + H2O2 = ?
show the reaction diagram
-
tyramine + NADPH + H+ + O2
show the reaction diagram
-
tyramine + NADPH + O2 = tyramine N-oxide + NADP+ + H2O
show the reaction diagram
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tyramine + FMNH + O2 = dopamine + FMN + H2O
show the reaction diagram
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tyramine + tetrahydrobiopterin + O2 = dopamine + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
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tyramine + ascorbate + O2 = 4-(2-aminoethyl)cyclohexa-3,5-diene-1,2-dione + dehydroascorbate + H2O
show the reaction diagram
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tyramine + O2 + H2O = (4-hydroxyphenyl)acetaldehyde + NH3 + H2O2
show the reaction diagram
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S-adenosyl-L-methionine + tyramine = N-methyltyramine + S-adenosyl-L-homocysteine
show the reaction diagram
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acetyl-CoA + p-tyramine = CoA + N-acetyl-p-tyramine
show the reaction diagram
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3'-phosphoadenylylsulfate + tyramine = adenosine 3',5'-bisphosphate + tyramine O-sulfate
show the reaction diagram
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3'-phosphoadenylylsulfate + tyramine = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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ATP + detyrosinated alpha-tubulin + tyramine = ?
show the reaction diagram
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ATP + tyramine + L-glutamate = ADP + phosphate + gamma-glutamyltyramine
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
tyramine-O-sulfate + H2O = tyramine + sulfate
show the reaction diagram
-
-
L-Tyrosine = Tyramine + CO2
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
typical inhibitors of catecholoxidase, also inhibit the phenoloxidase activity of activated hemocyanin
-
rate of ascorbate reduction of the E-Cu(II) form of TbetaM is also reduced at high tyramine
-
23% inhibition at 0.1 mM
-
competitive with L-Phe
-
at high concentrations
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and the hydroxyl derivative
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about 53% inhibition at 100 mM
-
13% inhibition with tyrosine at 3 mM and tyramine at 12 mM
-
inhibitor of hydrolysis for charged substrates
-
at concentration of 0.1 g/l about 2% less putrescine production
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1 mM inhibits Nalpha-gamma-L-glutamylhistamine synthesis by 94%; 1 mM inhibits synthesis of Nalpha-gamma-L-glutamylhistamine by 94%
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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) (40 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
121
-
-

KM Value (132 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.1
-
pH 7.0, 37°C
0.02
-
-
3.5
-
with 4-nitrophenyl sulfate as second substrate, pH 8, 37°C
8
-
-

Ki Value (43 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.2782
-
with dopamine as a substrate
13.7
-
-
0.039
-
-
1.08
-
substrate inhibition

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.04
-
IC50: 0.04 mM
20
-
IC50 above 20 mM, in the presence of 0.5 mM MnCl2, at 37°C

References & Links

Links to other databases for tyramine

ChEBI
PubChem
ChEBI
PubChem