Information on EC 2.3.1.87 - aralkylamine N-acetyltransferase

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The expected taxonomic range for this enzyme is: Eukaryota

EC NUMBER
COMMENTARY hide
2.3.1.87
-
RECOMMENDED NAME
GeneOntology No.
aralkylamine N-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + a 2-arylethylamine = CoA + an N-acetyl-2-arylethylamine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
serotonin and melatonin biosynthesis
-
-
Tryptophan metabolism
-
-
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
-
-
-
Manually annotated by BRENDA team
collected from NGM plates seeded with Escherichia coli NA22
UniProt
Manually annotated by BRENDA team
collected from NGM plates seeded with Escherichia coli NA22
UniProt
Manually annotated by BRENDA team
cDNA-coded arylalkylamine N-acetyltransferase
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
AANAT2
-
-
Manually annotated by BRENDA team
AANAT2
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Esox sp.
light regulation of circadian rhythm in melatonin secretion
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
giant freshwater prawn
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-
Manually annotated by BRENDA team
human filarial parasite
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Fischer
SwissProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
collected from an apple, Malus pumila, cv. Fuji, orchard at Akita, Japan
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-
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
trout
light regulation of circadian rhythm in melatonin secretion
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
the abnormal Bm-iAANAT is responsible for the mln mutant, phenotype, overview. The content of dopamine in the mln mutant is about 2times higher than in the wild-type. A greater accumulation of dopamine results from the functional deficiency of Bm-iAANAT in the mutant and that the excessive dopamine is converted into dopamine melanin, causing the darker color pattern of the sclerified regions in the mln mutant compared with the wild-type; the abnormal Bm-iAANAT is responsible for the mln mutant, phenotype, overview. The content of dopamine in the mln mutant is about 2times higher than in the wild-type. A greater accumulation of dopamine results from the functional deficiency of Bm-iAANAT in the mutant and that the excessive dopamine is converted into dopamine melanin, causing the darker color pattern of the sclerified regions in the mln mutant compared with the wild-type
metabolism
physiological function
additional information
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 + 2,5-dimethoxyphenylethylamine
CoA + N-acetyl-2,5-dimethoxyphenylethylamine
show the reaction diagram
-
68% 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
acetyl-CoA + 2-(2-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(2-chlorophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(3,4-dihydroxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dihydroxyphenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(3,4-dimethoxyphenyl)-ethylamine
CoA + N-acetyl-2-(3,4-dimethoxyphenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(3-chlorophenyl)-ethylamine
CoA + N-acetyl-2-(3-chlorophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(3-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(3-fluorophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(4-bromophenyl)-ethylamine
CoA + N-acetyl-2-(4-bromophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(4-chlorophenyl)ethylamine
CoA + N-acetyl-2-(4-chlorophenyl)ethylamine
show the reaction diagram
acetyl-CoA + 2-(4-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(4-fluorophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(p-fluorophenyl)-ethylamine
CoA + N-acetyl-2-(p-fluorophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(p-nitrophenyl)-ethylamine
CoA + N-acetyl-2-(p-nitrophenyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-(p-tolyl)-ethylamine
CoA + N-acetyl-2-(p-tolyl)-ethylamine
show the reaction diagram
acetyl-CoA + 2-fluorophenylethylamine
CoA + ?
show the reaction diagram
69% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-fluorophenylethylamine
CoA + N-acetyl-2-fluorophenylethylamine
show the reaction diagram
-
52% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 2-methoxyphenylethylamine
CoA + N-acetyl-2-methoxyphenylethylamine
show the reaction diagram
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-hydroxy-4-methoxyphenethylamine
CoA + N-acetyl-3-hydroxy-4-methoxyphenethylamine
show the reaction diagram
-
7.2% 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-hydroxyphenethylamine
CoA + N-acetyl-3-hydroxyphenethylamine
show the reaction diagram
-
36% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-indolebutylamine
CoA + N-acetyl-(3-indol-3-yl-butyl)-amine
show the reaction diagram
-
60-fold less efficiently than serotonin
-
-
?
acetyl-CoA + 3-indolepropylamine
CoA + N-acetyl-(3-indol-3-yl-propyl)-amine
show the reaction diagram
-
20-fold less efficiently than serotonin
-
-
?
acetyl-CoA + 3-methoxy-2-phenylethylamine
CoA + ?
show the reaction diagram
23% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxy-2-phenylethylamine
CoA + N-acetyl-3-methoxy-2-phenylethylamine
show the reaction diagram
-
55% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxytyramine
CoA + ?
show the reaction diagram
17% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 3-methoxytyramine
CoA + N-acetyl-3-methoxytyramine
show the reaction diagram
-
73% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonamide
CoA + ?
show the reaction diagram
-
1% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 4-(2-aminoethyl)-benzenesulfonyl fluoride
CoA + ?
show the reaction diagram
acetyl-CoA + 4-methoxyphenylethylamine
CoA + N-acetyl-4-methoxyphenylethylamine
show the reaction diagram
acetyl-CoA + 5-hydroxydopamine
CoA + N-acetyl-5-hydroxydopamine
show the reaction diagram
-
4.4% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 5-hydroxytryptamine
CoA + N-acetyl-5-hydroxytryptamine
show the reaction diagram
acetyl-CoA + 5-methoxytryptamine
CoA + N-acetyl-5-methoxytryptamine
show the reaction diagram
acetyl-CoA + 6-fluorotryptamine
CoA + N-acetyl-6-fluorotryptamine
show the reaction diagram
acetyl-CoA + 6-hydroxydopamine
CoA + ?
show the reaction diagram
51% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + 6-hydroxydopamine
CoA + N-acetyl-6-hydroxydopamine
show the reaction diagram
-
1.5% of the activity with 2-phenylethylamine
-
-
?
acetyl-CoA + a 2-arylethylamine
CoA + an N-acetyl-2-arylethylamine
show the reaction diagram
acetyl-CoA + alpha-methyltryptamine
CoA + N-acetyl-alpha-methyltryptamine
show the reaction diagram
-
racemic, 9:1 stereoselectivity for R-enantiomer, less efficiently than serotonin
-
-
?
acetyl-CoA + beta-phenylethylamine
CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
acetyl-CoA + dopamine
CoA + N-acetyldopamine
show the reaction diagram
acetyl-CoA + histamine
CoA + N-acetylhistamine
show the reaction diagram
-
-
-
?
acetyl-CoA + methoxytryptamine
CoA + N-acetylmethoxytryptamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + Nomega-methyltryptamine
CoA + ?
show the reaction diagram
-
less efficiently than serotonin
-
-
?
acetyl-CoA + norepinephrine
CoA + N-acetylnorepinephrine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + norepinephrine
CoA + N-acetyltyramine
show the reaction diagram
acetyl-CoA + octopamine
CoA + N-acetyloctopamine
show the reaction diagram
acetyl-CoA + p-phenetidine
CoA + N-(4-ethoxyphenyl)-aecetamide
show the reaction diagram
-
-
-
-
?
acetyl-CoA + phenylethylamine
CoA + N-acetyl-phenylethylamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + phenylethylamine
CoA + N-acetylphenylethylamine
show the reaction diagram
acetyl-CoA + phenylethylamine
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 + tryptamine
N-acetyltryptamine + CoA
show the reaction diagram
-
-
-
-
?
acetyl-CoA + tryptophol
CoA + N-acetyltryptophol
show the reaction diagram
-
structural analogue to tryptamine
-
-
?
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
additional information
?
-
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 + a 2-arylethylamine
CoA + an N-acetyl-2-arylethylamine
show the reaction diagram
acetyl-CoA + dopamine
CoA + N-acetyldopamine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + histamine
CoA + N-acetylhistamine
show the reaction diagram
Q16KL9
-
-
-
?
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
acetyl-CoA + tryptamine
CoA + N-acetyltryptamine
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
NaCl
optimal activity at 0.5 M
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-bromo-N-[2-(5-fluoro-1-benzothien-3-yl)ethyl]acetamide
-
IC50: 0.00039 mM
9-carboxy-11-nor-delta-9-tetrahydrocannabinol
-
significantly reduces norepinephrine-induced arylalkylamine N-acetyltransferase activity
acetyl-CoA-tryptamine
alpha-trifluoromethyltryptamine
-
modest, competitive
bromoacetyltryptamine
cannabidiol
-
significantly reduces norepinephrine-induced arylalkylamine N-acetyltransferase activity
cannabinoid
-
cannabinoids inhibit AANAT activity and attenuate melatonin biosynthesis through intracellular actions without involvement of classical cannabinoid receptor-dependent signaling cascades
cannabinol
-
significantly reduces norepinephrine-induced arylalkylamine N-acetyltransferase activity
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
-
fluorescent variant of CoA-T, a bisubstrate inhibitor, synthesis and enzyme binding structure, molecular modelling, overview
desulfo-CoA
-
dead end inhibitor analog, competitive versus CoA
Disulfides
glutathione
-
reversible, acetyl-CoA protects
Melatonin
methyl 3-[2-[(bromoacetyl)amino]ethyl]-1-benzothiophene-5-carboxylate
-
IC50: 0.00225 mM
N-acetylserotonin
IC50: 0.68 mM; very slightly
N-ethylmaleimide
-
irreversible, acetyl-CoA protects
N-[2-(2-benzyl-5-methoxy-benzofuran-3-yl)ethyl]iodoacetamide
-
IC50: 0.0087 mM
N-[2-(2-phenyl-benzo [b]thiophen-3-yl)ethyl]bromoacetamide
-
IC50: 0.001 mM
N-[2-(3-ethyl-7-methoxy-napht-1-yl)ethyl]iodoacetamide
-
IC50: 0.0006 mM
N-[2-(5-bromo-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
-
IC50: 0.00378 mM
N-[2-(5-chloro-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
-
IC50: 0.00018 mM
N-[2-(5-ethyl-1-benzothien-3-yl)ethyl]-2-iodoacetamide
-
IC50: 0.002 mM
N-[2-(5-ethyl-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
-
IC50: 0.00071 mM
N-[2-(5-fluoro-1H-indol-3-yl)ethyl]bromoacetamide
-
IC50: 0.0056 mM
N-[2-(5-hydroxy-benzo[b]thiophen-3-yl)ethyl]bromoacetamide
-
IC50: 0.00018 mM
N-[2-(7-ethyl-1,2,3,4-tetrahydronapht-1-yl)ethyl]iodooacetamide
-
IC50: above 0.1 mM
N-[2-(7-ethyl-napht-1-yl)ethyl]-bromoacetamide
-
IC50: 0.00177 mM
N-[2-(7-hydroxy-naphth-1-yl)ethyl]bromoacetamide
-
IC50: 0.00072 mM
N-[2-(7-methoxy-3-(3-trifluoromethylphenyl)-napht-1-yl)ethyl]iodoacetamide
-
IC50: 0.045 mM
N-[2-(7-methoxy-8-propenyl-napht-1-yl)ethyl]-iodoacetamide
-
IC50: above 0.1 mM
N-[2-(7-methoxy-napht-1-yl)ethyl]bromoacetamide
-
IC50: 0.002 mM
N-[2-(7-propoxy-napht-1-yl)ethyl]iodoacetamide
-
IC50: 0.0042 mM
oxygen
-
reversible, acetyl-CoA protects
p-chloro-mercuribenzoate
-
-
Peptides containing a disulfide bond
S 20251
S 23823
S 27244
S 27481
S 28036
serotonin
tryptamine
tryptamine-coenzyme A
-
a bisubstrate inhibitor, enzyme binding structure, molecular modelling, overview
tryptophol
-
dead end inhibitor analog, competitive versus tryptamine
UV light
-
NAT activity and melatonin content are suppressed by blue light of 450 nm wavelength, no effects of red light at 650 nm.UV radiation has intensity-dependent dual effects on the NAT activity and melatonin content: it is supressing at low intensity and activating at high intensity irradiation, overview
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14-3-3 protein
-
14-3-3zeta, interaction with the phosphorylated enzyme activates activity, binding analysis, overview
-
4beta-phorbol 12-myristate 13-acetate
-
stimulates activity on a posttranscriptional level in a cAMP-independent manner
5-hydroxytryptophan
-
activates, best at 0.1 mM
forskolin
-
decreases KM-value for tryptamine by 32%
leptin
-
increases enzyme activity only in fed fish not in fasted fish, independently of the seasons
-
Melatonin
-
activates, best at 0.1 mM
N-acetylserotonin
-
activates, best at 0.1 mM
phorbol 12,13-dibutyrate
-
stimulates activity on a posttranscriptional level
phorbol 12-myristate 13-acetate
-
decreases KM-value for tryptamine by 44%
phosphate
optimal activity at 0.1 M; optimal activity at 0.3 M
serotonin
-
activates, best at 0.1 mM
UV light
-
NAT activity and melatonin content are suppressed by blue light of 450 nm wavelength, no effects of red light at 650 nm.UV radiation has intensity-dependent dual effects on the NAT activity and melatonin content: it is supressing at low intensity and activating at high intensity irradiation, overview
-
additional information
-
the enzyme is activated by Ser and Thr phosphorylations, e.g. AANAT Thr31 phosphorylation on its own can enhance catalytic efficiency up to 7fold
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.47
2,5-dimethoxyphenylethylamine
-
pH 6.8, 37C
0.34 - 3.46
2-(2,3-dichlorophenyl)-ethylamine
0.9 - 2.74
2-(2-chlorophenyl)-ethylamine
1.76
2-(3,4-dihydroxyphenyl)-ethylamine
-
pH 6.8, 37C
0.62 - 1.31
2-(3-chlorophenyl)-ethylamine
1.1 - 1.65
2-(3-fluorophenyl)-ethylamine
0.75 - 1.55
2-(4-bromophenyl)-ethylamine
2.33
2-(4-chlorophenyl)ethylamine
-
pH 6.8, 37C
1.28 - 2.2
2-(4-fluorophenyl)-ethylamine
0.98 - 1.91
2-(p-fluorophenyl)-ethylamine
1.405
2-(p-nitrophenyl)-ethylamine
-
pH 6.8, 37C
1.17 - 1.58
2-(p-tolyl)-ethylamine
1.37
2-fluorophenylethylamine
0.49 - 1.3
2-methoxyphenylethylamine
0.17 - 9.5
2-Phenylethylamine
2.07
3-methoxy-2-phenylethylamine
-
pH 6.8, 37C
1.815
3-methoxytyramine
-
pH 6.8, 37C
0.024
5-hydroxytryptamine
-
-
0.2
5-methoxytryptamine
-
-
1.9
6-Hydroxydopamine
pH 6.8, 37C
0.00031 - 1.11
acetyl-CoA
0.009 - 0.173
beta-phenylethylamine
0.19 - 0.48
dopamine
0.18 - 0.23
methoxytryptamine
0.16 - 0.17
norepinephrine
0.002 - 0.14
octopamine
0.011
p-phenetidine
-
-
0.34
Phenylethylamine
-
0.05 - 2.05
serotonin
0.0017 - 4
tryptamine
0.0015 - 1.25
tyramine
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.65 - 7.3
dopamine
3.74 - 7.69
methoxytryptamine
3.17 - 7.76
norepinephrine
2.56 - 7.26
octopamine
3.47 - 25.9
serotonin
3.05 - 7.345
tryptamine
3.16 - 6.775
tyramine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
210 - 290
serotonin
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0003
CoA-S-N-acetyl-7-hydroxynaphthylethylamine
-
-
0.00015
tryptamine-CoA
-
-
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 - 0.0008
acetyl-CoA-tryptamine
0.00128 - 0.0051
bromoacetyltryptamine
0.16 - 0.26
Melatonin
0.00225
methyl 3-[2-[(bromoacetyl)amino]ethyl]-1-benzothiophene-5-carboxylate
Homo sapiens
-
IC50: 0.00225 mM
0.68
N-acetylserotonin
Sparus aurata
Q68SL6
IC50: 0.68 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
0.0013 - 0.0024
S 20251
0.005 - 0.031
S 23823
0.00026 - 0.00072
S 27244
0.00018 - 0.0004
S 27481
0.00073 - 0.0056
S 28036
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000027
-
enzyme activity on pineal in pineal gland from quiescent phase, pH 6.5, 25C
0.000036
-
enzyme activity on pineal in pineal gland from progressive phase, pH 6.5, 25C
0.000039
-
enzyme activity on pineal in pineal gland from breeding phase, pH 6.5, 25C
0.000043
-
enzyme activity on pineal in pineal gland from regressive phase, pH 6.5, 25C
0.000195
-
-
7.17
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3
-
assay at
7.6
-
assay at
9.5
-
two pH optima, pH 6.0 and pH 9.5, which change during oocyte maturation
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8
-
pH 6.5: about 30% of maximal activity, pH 8.0: about 50% of maximal activity
7 - 8
pH 7.0: abut 40% of maximal activity, pH 8.0: about 50% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperature
30
-
assay at
additional information
-
pineal AANAT responds to temperature in a species-specific manner
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 40
0C: about 55% of maximal activity, 47C: about 50% of maximal activity
20 - 47
20C: about 40% of maximal activity, 47C: about 35% of maximal activity
additional information
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
female. The left gland contains higher activity than the right gland
Manually annotated by BRENDA team
-
non-diapause eggs and diapause eggs
Manually annotated by BRENDA team
AANAT2 is expressed only in the muscular layer
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
AANAT2 is expressed only in the muscular layer
Manually annotated by BRENDA team
esophagus, stomach, pyloric ceca, foregut, midgut, hindgut. AANAT2 is expressed only in the muscular layer of all segments. No significant differences are obtained among the different segments evaluated
Manually annotated by BRENDA team
AANAT2 is expressed only in the muscular layer
Manually annotated by BRENDA team
-
isozyme AANAT2 developmental expression pattern, overview
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
photoreceptor cells, ependymal cells of the 3rd ventricle and discrete cells of the suprachiasmatic area. Expression of AANAT2 and absence of AANAT2
Manually annotated by BRENDA team
-
mainly pars tuberalis, much less than in pineal gland, probably different regulation
Manually annotated by BRENDA team
AANAT2 is expressed only in the muscular layer
Manually annotated by BRENDA team
AANAT2 is expressed only in the muscular layer
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26000
-
liver, gel filtration
37000
-
gel filtration
39000
-
pineal gland, gel filtration
80000 - 100000
-
gel filtration
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 28000, SDS-PAGE
tetramer
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
additional information
-
lacks cAMP-dependent protein kinase phosphorylation sites in the N- and C-terminal regions
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging-drop vapor diffusion method, mixing of 0.001 ml of both protein and reservoir solution, equilibration against 0.15 ml of reservoir solution containing 0.17 M ammonium acetate, 25.5% PEG 4000, and 17% glycerol, and 0.1 M sodium citrate, pH 5.6, X-ray diffraction structure determination and analysis, molecular replacement, modeling
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
stable for 3 h
45 - 65
-
5 min, complete inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA stabilizes
ATP stabilizes
cysteamine stabilizes
-
freezing markedly decreases activity
polyanions stabilize
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-2C, up to 72 h
4C, 25% loss of activity within 48 h
-
4C, t1/2: 24 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography on Sepharose CoA
-
denaturation/renaturation process in which the enzyme is immobilized on an affinity chromatography column
partial
recombinant aaNAT1-4, aaNAT5b, aaNAT7, aaNAT9, and aaNAT11 by chinin affinity and ion exchange chromatography, and gel filtration
-
recombinant N-terminally GST-tagged AANAT from Escherichia coli strain BL21 by glutathione affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AANAT, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic tree, expression in Micro-Tom, a model cultivar of Solanum lycopersicum, transgenic Micro-Tom exhibits higher melatonin content compared with wild type. Expression of N-terminally GST-tagged AANAT in Escherichia coli strain BL21
-
aaNAT1-4, aaNAT5b, aaNAT7, aaNAT9, and aaNAT11, homology sequence analysis, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression profiling of aaNAT1 aaNAT2 based on real time quantitative reverse transcriptase PCR, individual recombinant expression
-
AANAT2, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression of the GST-tagged enzyme from pGEX4T1 expression vector
baculovirus infection of Tn5 insect cells
DNA and amino acid sequence determination and analysis, phylogenetic tree
DNA and amino acid sequence determination and analysis, quantitative expression analysis; DNA and amino acid sequence determination and analysis, quantitative expression analysis; DNA and amino acid sequence determination and analysis, quantitative expression analysis
expression in Escherichia coli
expression in HEK293 cells and in Escherichia coli
expression of AANAT-(2207) and mutant enzymes in Escherichia coli strain BL21(DE3)
-
expression of truncation mutants in Escherichia coli strain BL21(DE3)
-
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
-
gene AANAT2, DNA and amino acid sequence determination and analysis, developmental expression analysis by quantitative real time PCR analysis, phylogenetic analysis, overview
-
genotyping in Caucasian population, screening for AANAT mutations
-
phylogenetic tree and analysis
recombinant Bm-iAANAT protein is expressed in Sf9 cells by a baculovirus expression system
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H120Q
-
crystallographic studies, role in enzymic reaction
H122Q
-
crystallographic studies, role in enzymic reaction
H122Q/H120Q
-
crystallographic studies, role in enzymic reaction
I57A/V59A
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64A
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64G
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
P64W
-
site-directed mutagenesis, the mutant shows reduced enzyme activity and altered inhibitor binding compared to the wild-type enzyme
S205A
-
1.6fold increase in Km-value for tryptamine compared to wild-type enzyme
T31A
-
1.7fold increase in KM-value for tryptamine compared to wild-type enzyme
Y168F
-
crystallographic studies, role in enzymic reaction
C177A
-
fully active, not sensitive to oxidation or N-ethylmaleimide
C61A
-
fully active, not sensitive to oxidation or N-ethylmaleimide
H28Y
H28Y mutation in NAT is the cause of reduced NAT levels in vivo
S192V
-
decrease in Km-value obtained by treatment with phorbol 12-myristate 13-acetate or forskolin is similar to the decrease observed in wild-type cells
T127V
-
decrease in Km-value obtained by treatment with phorbol 12-myristate 13-acetate or forskolin is similar to the decrease observed in wild-type cells
T29V
-
mutant enzyme shows an increase in Km-value obtained by treatment with phorbol 12-myristate 13-acetate or forskolin, decrease in Km-value is observed in wild-type cells
T29V/S203G
-
mutant enzyme shows an increase in Km-value obtained by treatment with phorbol 12-myristate 13-acetate or forskolin, decrease in Km-value is observed in wild-type cells
additional information