Information on EC 2.3.1.87 - aralkylamine N-acetyltransferase and Organism(s) Homo sapiens

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The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.87
-
RECOMMENDED NAME
GeneOntology No.
aralkylamine N-acetyltransferase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
serotonin and melatonin biosynthesis
-
-
Tryptophan metabolism
-
-
Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:2-arylethylamine N-acetyltransferase
Narrow specificity towards 2-arylethylamines, including serotonin (5-hydroxytryptamine), tryptamine, 5-methoxytryptamine and phenylethylamine. This is the penultimate enzyme in the production of melatonin (5-methoxy-N-acetyltryptamine) and controls its synthesis (cf. EC 2.1.1.4, acetylserotonin O-methyltransferase). Differs from EC 2.3.1.5 arylamine N-acetyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
92941-56-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + 2,5-dimethoxyphenylethylamine
CoA + ?
show the reaction diagram
24% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(2,3-dichlorophenyl)-ethylamine
CoA + N-acetyl-2-(2,3-dichlorophenyl)-ethylamine
show the reaction diagram
78% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(2-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(2-chlorophenyl)-ethylamine
show the reaction diagram
130% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3,4-dihydroxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dihydroxyphenyl)-ethylamine
show the reaction diagram
7% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3,4-dimethoxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dimethoxyphenyl)-ethylamine
show the reaction diagram
4.4% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(3-chlorophenyl)-ethylamine
show the reaction diagram
67% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(3-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(3-fluorophenyl)-ethylamine
show the reaction diagram
65% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-bromophenyl)-ethylamine
CoA + N-acetyl-2-(4-bromophenyl)-ethylamine
show the reaction diagram
48% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-chlorophenyl)ethylamine
CoA + N-acetyl-2-(4-chlorophenyl)ethylamine
show the reaction diagram
68% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(4-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(4-fluorophenyl)-ethylamine
show the reaction diagram
116% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(p-fluorophenyl)-ethylamine
show the reaction diagram
56% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-nitrophenyl)-ethylamine
CoA + N-acetyl-2-(p-nitrophenyl)-ethylamine
show the reaction diagram
9% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-(p-tolyl)-ethylamine
CoA + N-acetyl-2-(p-tolyl)-ethylamine
show the reaction diagram
60% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-fluorophenylethylamine
CoA + ?
show the reaction diagram
69% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-methoxyphenylethylamine
CoA + N-acetyl-2-methoxyphenylethylamine
show the reaction diagram
52% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-phenylethylamine
CoA + N-acetyl-2-phenylethylamine
show the reaction diagram
-
-
-
?
acetyl-CoA + 3-hydroxy-4-methoxyphenethylamine
CoA + ?
show the reaction diagram
1% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-hydroxyphenethylamine
CoA + ?
show the reaction diagram
24% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxy-2-phenylethylamine
CoA + ?
show the reaction diagram
23% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxytyramine
CoA + ?
show the reaction diagram
17% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonyl fluoride
CoA + ?
show the reaction diagram
8% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-methoxyphenylethylamine
CoA + N-acetyl-4-methoxyphenylethylamine
show the reaction diagram
11% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 5-methoxytryptamine
CoA + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 6-hydroxydopamine
CoA + ?
show the reaction diagram
51% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + beta-phenylethylamine
CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
-
-
-
-
?
acetyl-CoA + phenylethylamine
CoA + N-acetyl-phenylethylamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
acetyl-CoA + tryptamine
CoA + N-acetyltryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + tyramine
CoA + ?
show the reaction diagram
8% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + tyramine
CoA + N-acetyltyramine
show the reaction diagram
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very poor substrate
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-
?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
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-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-bromo-N-[2-(5-fluoro-1-benzothien-3-yl)ethyl]acetamide
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IC50: 0.00039 mM
acetyl-CoA-tryptamine
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IC50: 0.00041 mM, GST-AANAT fusion protein
bromoacetyltryptamine
Melatonin
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IC50 0.16 mM
methyl 3-[2-[(bromoacetyl)amino]ethyl]-1-benzothiophene-5-carboxylate
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IC50: 0.00225 mM
N-[2-(2-benzyl-5-methoxy-benzofuran-3-yl)ethyl]iodoacetamide
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IC50: 0.0087 mM
N-[2-(2-phenyl-benzo [b]thiophen-3-yl)ethyl]bromoacetamide
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IC50: 0.001 mM
N-[2-(3-ethyl-7-methoxy-napht-1-yl)ethyl]iodoacetamide
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IC50: 0.0006 mM
N-[2-(5-bromo-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
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IC50: 0.00378 mM
N-[2-(5-chloro-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
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IC50: 0.00018 mM
N-[2-(5-ethyl-1-benzothien-3-yl)ethyl]-2-iodoacetamide
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IC50: 0.002 mM
N-[2-(5-ethyl-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
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IC50: 0.00071 mM
N-[2-(5-fluoro-1H-indol-3-yl)ethyl]bromoacetamide
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IC50: 0.0056 mM
N-[2-(5-hydroxy-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
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IC50: 0.00018 mM
N-[2-(7-ethyl-1,2,3,4-tetrahydronapht-1-yl)ethyl]iodooacetamide
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IC50: above 0.1 mM
N-[2-(7-ethyl-napht-1-yl)ethyl]-bromoacetamide
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IC50: 0.00177 mM
N-[2-(7-hydroxy-naphth-1-yl)ethyl]bromoacetamide
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IC50: 0.00072 mM
N-[2-(7-methoxy-3-(3-trifluoromethylphenyl)-napht-1-yl)ethyl]iodoacetamide
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IC50: 0.045 mM
N-[2-(7-methoxy-8-propenyl-napht-1-yl)ethyl]-iodoacetamide
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IC50: above 0.1 mM
N-[2-(7-methoxy-napht-1-yl)ethyl]bromoacetamide
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IC50: 0.002 mM
N-[2-(7-propoxy-napht-1-yl)ethyl]iodoacetamide
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IC50: 0.0042 mM
S 20251
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IC50: 0.002 mM, GST-AANAT fusion protein
S 23823
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IC50: 0.005 mM, GST-AANAT fusion protein
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S 27244
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IC50: 0.00072 mM, GST-AANAT fusion protein
S 27481
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IC50: 0.00018 mM, GST-AANAT fusion protein
S 28036
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IC50: 0.0056 mM,GST-AANAT fusion protein
additional information
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inhibition values of peptide inhibitors
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14-3-3 protein
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14-3-3zeta, interaction with the phosphorylated enzyme activates activity, binding analysis, overview
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additional information
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the enzyme is activated by Ser and Thr phosphorylations, e.g. AANAT Thr31 phosphorylation on its own can enhance catalytic efficiency up to 7fold
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.34
2-(2,3-dichlorophenyl)-ethylamine
-
pH 6.8, 37C
2.74
2-(2-chlorophenyl)-ethylamine
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pH 6.8, 37C
0.62
2-(3-chlorophenyl)-ethylamine
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pH 6.8, 37C
1.1
2-(3-fluorophenyl)-ethylamine
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pH 6.8, 37C
0.75
2-(4-bromophenyl)-ethylamine
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pH 6.8, 37C
2.2
2-(4-fluorophenyl)-ethylamine
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pH 6.8, 37C
0.98
2-(p-fluorophenyl)-ethylamine
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pH 6.8, 37C
1.17
2-(p-tolyl)-ethylamine
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pH 6.8, 37C
1.37
2-fluorophenylethylamine
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pH 6.8, 37C
1.3
2-methoxyphenylethylamine
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pH 6.8, 37C
0.17
2-Phenylethylamine
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pH 6.8, 37C
0.2
5-methoxytryptamine
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-
1.9
6-Hydroxydopamine
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pH 6.8, 37C
0.53 - 0.55
acetyl-CoA
0.173
beta-phenylethylamine
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-
0.06 - 1.35
serotonin
0.91
tryptamine
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-
additional information
additional information
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kinetics of recombinant partially phosphorylated wild-type and mutant enzymes, overview
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17.3 - 25.9
serotonin
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
210 - 290
serotonin
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00039
2-bromo-N-[2-(5-fluoro-1-benzothien-3-yl)ethyl]acetamide
Homo sapiens
-
IC50: 0.00039 mM
0.00041
acetyl-CoA-tryptamine
Homo sapiens
-
IC50: 0.00041 mM, GST-AANAT fusion protein
0.0014 - 0.00143
bromoacetyltryptamine
0.16
Melatonin
Homo sapiens
-
IC50 0.16 mM
0.00225
methyl 3-[2-[(bromoacetyl)amino]ethyl]-1-benzothiophene-5-carboxylate
Homo sapiens
-
IC50: 0.00225 mM
0.0087
N-[2-(2-benzyl-5-methoxy-benzofuran-3-yl)ethyl]iodoacetamide
Homo sapiens
-
IC50: 0.0087 mM
0.001
N-[2-(2-phenyl-benzo [b]thiophen-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.001 mM
0.0006
N-[2-(3-ethyl-7-methoxy-napht-1-yl)ethyl]iodoacetamide
Homo sapiens
-
IC50: 0.0006 mM
0.00378
N-[2-(5-bromo-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.00378 mM
0.00018
N-[2-(5-chloro-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.00018 mM
0.002
N-[2-(5-ethyl-1-benzothien-3-yl)ethyl]-2-iodoacetamide
Homo sapiens
-
IC50: 0.002 mM
0.00071
N-[2-(5-ethyl-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.00071 mM
0.0056
N-[2-(5-fluoro-1H-indol-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.0056 mM
0.00018
N-[2-(5-hydroxy-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.00018 mM
0.1
N-[2-(7-ethyl-1,2,3,4-tetrahydronapht-1-yl)ethyl]iodooacetamide
Homo sapiens
-
IC50: above 0.1 mM
0.00177
N-[2-(7-ethyl-napht-1-yl)ethyl]-bromoacetamide
Homo sapiens
-
IC50: 0.00177 mM
0.00072
N-[2-(7-hydroxy-naphth-1-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.00072 mM
0.045
N-[2-(7-methoxy-3-(3-trifluoromethylphenyl)-napht-1-yl)ethyl]iodoacetamide
Homo sapiens
-
IC50: 0.045 mM
0.1
N-[2-(7-methoxy-8-propenyl-napht-1-yl)ethyl]-iodoacetamide
Homo sapiens
-
IC50: above 0.1 mM
0.002
N-[2-(7-methoxy-napht-1-yl)ethyl]bromoacetamide
Homo sapiens
-
IC50: 0.002 mM
0.0042
N-[2-(7-propoxy-napht-1-yl)ethyl]iodoacetamide
Homo sapiens
-
IC50: 0.0042 mM
0.002
S 20251
Homo sapiens
-
IC50: 0.002 mM, GST-AANAT fusion protein
0.005
S 23823
Homo sapiens
-
IC50: 0.005 mM, GST-AANAT fusion protein
-
0.00072
S 27244
Homo sapiens
-
IC50: 0.00072 mM, GST-AANAT fusion protein
0.00018
S 27481
Homo sapiens
-
IC50: 0.00018 mM, GST-AANAT fusion protein
0.0056
S 28036
Homo sapiens
-
IC50: 0.0056 mM,GST-AANAT fusion protein
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
-
phosphorylation on key AANAT Ser and Thr residues by protein kinase A results in 14-3-3 protein recruitment and changes in catalytic activity and protein stability. AANAT Thr31 phosphorylation on its own can enhance catalytic efficiency up to 7fold, but the catalytic profile is largely abolished by double phosphorylation at Thr31 and Ser205. Influence of phosphorylations on enzyme activity, overview
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular modeling, docking of N-acetylserotonin and screening for potential ligands. N-[2-(5-hydroxy-1H-indol-3-yl)ethy1]-3-(4-hydroxyphenyl)-2-propenamide show least binding energy, i.e. -9.38 Kcal/mol
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
denaturation/renaturation process in which the enzyme is immobilized on an affinity chromatography column
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
baculovirus infection of Tn5 insect cells
-
expression in Escherichia coli
-
expression of truncation mutants in Escherichia coli strain BL21(DE3)
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functional ectopic overexpression of human serotonin N-acetyltransferase under the constitutive ubiquitin promoter in transgenic Oryza sativa cv. Dongjin seedlings using Agrobacterium-mediated gene transformation leading to elevated synthesis of N-acetylserotonin and melatonin in the transgenic rice plants, phenotype, overview
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genotyping in Caucasian population, screening for AANAT mutations
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information