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Information on EC 2.3.1.87 - aralkylamine N-acetyltransferase and Organism(s) Rattus norvegicus and UniProt Accession Q64666

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IUBMB Comments
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.
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Rattus norvegicus
UNIPROT: Q64666
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The taxonomic range for the selected organisms is: Rattus norvegicus
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
aanat, aa-nat, snat2, arylalkylamine n-acetyltransferase, snat1, aanat2, aanat1, serotonin-n-acetyltransferase, aralkylamine n-acetyltransferase, bm-iaanat, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
AA-NAT
-
-
-
-
AANAT
acetyl-CoA:aralkylamine N-acetyltransferase
-
-
-
-
acetyltransferase, arylalkylamine N-
-
-
-
-
arylalkylamine N-acetyltransferase
-
-
-
-
N-acetyltransferase
-
-
-
-
serotonin acetylase
-
-
-
-
serotonin acetyltransferase
-
-
-
-
serotonin N-acetyltransferase
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
-
-
-
-
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
-
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-phenylethylamine
CoA + N-acetyl-2-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 + 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 + beta-phenylethylamine
CoA + N-(2-phenylethyl)-acetaminde
show the reaction diagram
acetyl-CoA + serotonin
CoA + N-acetylserotonin
show the reaction diagram
acetyl-CoA + tryptamine
CoA + N-acetyltryptamine
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
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
-
initial reaction in melatonin synthesis from serotonin
-
-
?
additional information
?
-
overexpression of inducible cAMP early repressor can suppress the norepinephrine induction of aa-nat
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
activation by salts as a function of ionic strength
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9-carboxy-11-nor-delta-9-tetrahydrocannabinol
significantly reduces norepinephrine-induced arylalkylamine N-acetyltransferase activity
acetyl-CoA-tryptamine
IC50: 0.0008 mM, GST-AANAT fusion protein
bromoacetyltryptamine
IC50: 0.0051 mM, GST-AANAT fusion protein
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
glutathione
reversible, acetyl-CoA protects
N-ethylmaleimide
irreversible, acetyl-CoA protects
oxygen
reversible, acetyl-CoA protects
S 20251
IC50: 0.0024 mM, GST-AANAT fusion protein
S 23823
IC50: 0.031 mM, GST-AANAT fusion protein
-
S 27244
IC50: 0.00036 mM, GST-AANAT fusion protein
S 27481
IC50: 0.0004 mM, GST-AANAT fusion protein
S 28036
IC50: 0.0017 mM, GST-AANAT fusion protein
Disulfides
-
in vivo and in vitro, reversible by dithiothreitol
Peptides containing a disulfide bond
-
-
-
Zn2+
-
at low concentration
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
forskolin
-
decreases KM-value for tryptamine by 32%
phorbol 12-myristate 13-acetate
-
decreases KM-value for tryptamine by 44%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9.5
2-Phenylethylamine
pH 6.8, 37°C
0.65
acetyl-CoA
pH 6.8, 37°C
1.7
serotonin
pH 6.8, 37°C
0.05 - 0.125
acetyl-CoA
2
serotonin
-
-
0.24 - 0.6
tryptamine
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0008
acetyl-CoA-tryptamine
Rattus norvegicus
IC50: 0.0008 mM, GST-AANAT fusion protein
0.0051
bromoacetyltryptamine
Rattus norvegicus
IC50: 0.0051 mM, GST-AANAT fusion protein
0.0024
S 20251
Rattus norvegicus
IC50: 0.0024 mM, GST-AANAT fusion protein
0.031
S 23823
Rattus norvegicus
IC50: 0.031 mM, GST-AANAT fusion protein
-
0.00036
S 27244
Rattus norvegicus
IC50: 0.00036 mM, GST-AANAT fusion protein
0.0004
S 27481
Rattus norvegicus
IC50: 0.0004 mM, GST-AANAT fusion protein
0.0017
S 28036
Rattus norvegicus
IC50: 0.0017 mM, GST-AANAT fusion protein
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
treatment of pinealocytes with norepinephrine causes an increase in the mRNA and protein levels of MKP-1 and AA-NAT, as well as in the AA-NAT activity
Manually annotated by BRENDA team
-
suprachiasmatic nucleus
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
N-terminally acetylated Ac-AANAT is degraded through the recognition of its N-terminally acetylated N-terminal Met residue by the Ac/N-end rule pathway, whereas the non-N-terminally acetylated AANAT is targeted by the Arg/N-end rule pathway, which recognizes the unacetylated N-terminal Met-Leu sequence of rat AANAT. Degradation of Lys8Arg mutants of rat AANAT is mediated by polyubiquitylation of its Lys residue(s)
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SNAT_RAT
205
0
23142
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10000
-
4 * 10000, pineal gland, gel filtration in the presence of cysteamine
11000
-
x * 11000, SDS-PAGE
12000
-
2 * 12000, liver, gel filtration in the presence of cysteamine
26000
-
liver, gel filtration
30000
-
gel filtration with sodium citrate
39000
-
pineal gland, gel filtration
additional information
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 11000, SDS-PAGE
dimer
-
2 * 12000, liver, gel filtration in the presence of cysteamine
tetramer
-
4 * 10000, pineal gland, gel filtration in the presence of cysteamine
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
-
phosphorylated at Thr29 by protein kinase C activation through the alpha1-adrenergic receptor in rat pineal glands. Phosphorylation may contribute to the stability and activity of the enzyme
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA stabilizes
-
ATP stabilizes
-
cysteamine stabilizes
-
freezing markedly decreases activity
-
polyanions stabilize
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-2°C, up to 72 h
-
4°C, t1/2: 24 h
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in HEK293 cells and in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
nocturnal elevation of AANAT protein is dependent on the rhythmic changes of heterogeneous ribonucleoprotein R, whose levels are elevated in the pineal gland during nighttime. Increases in heterogeneous ribonucleoprotein R additionally improve AANAT production in rat pinealocytes under norepinephrine treatment
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fajardo, N.; Abreu, P.; Alonso, R.
Determination of kinetic properties of serotonin-N-acetyltransferase in bovine pineal gland using HPLC with fluorimetric detection
J. Pineal Res.
13
80-84
1992
Bos taurus, Rattus norvegicus
Manually annotated by BRENDA team
Morrissey, J.J.; Edwards, S.B.; Lovenberg, W.
Comparison of rat pineal gland and rat liver serotonin-N-acetyltransferase
Biochem. Biophys. Res. Commun.
77
118-123
1977
Rattus norvegicus
Manually annotated by BRENDA team
Namboodiri, M.A.A.; Dubbels, R.; Klein, D.C.
Arylalkylamine N-acetyltransferase from mammalian pineal gland
Methods Enzymol.
142
583-590
1987
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Voisin, P.; Namboodiri, M.A.A.; Klein, D.C.
Arylamine N-acetyltransferase and arylalkylamine N-acetyltransferase in the mammalian pineal gland
J. Biol. Chem.
259
10913-10918
1984
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Namboodiri, M.A.A.; Brownstein, M.J.; Voisin, P.; Weller, J.L.; Klein, D.C.
A simple and rapid method for the purification of ovine pineal arylalkylamine N-acetyltransferase
J. Neurochem.
48
580-585
1987
Ovis aries, Rattus norvegicus
Manually annotated by BRENDA team
Namboodiri, M.A.A.; Brownstein, M.J.; Weller, J.L.; Voisin, P.; Klein, D.C.
Multiple forms of arylalkylamine N-acetyltransferases in the rat pineal gland: purification of one molecular form
J. Pineal Res.
4
235-246
1987
Rattus norvegicus
Manually annotated by BRENDA team
Deguchi, T.
Characteristics of serotonin-acetyl coenzyme A N-acetyltransferase in pineal gland of rat
J. Neurochem.
24
1083-1085
1975
Rattus norvegicus
Manually annotated by BRENDA team
Hamada, T.; Ootomi, M.; Horikawa, K.; Niki, T.; Wakamatu, H.; Ishida, N.
The expression of the melatonin synthesis enzyme: arylalkylamine N-acetyltransferase in the suprachiasmatic nucleus of rat brain
Biochem. Biophys. Res. Commun.
258
772-777
1999
Rattus norvegicus
Manually annotated by BRENDA team
Tsuboi, S.; Kotani, Y.; Ogawa, K.i.; Hatanaka, T.; Yatsushiro, S.; Otsuka, M.; Moriyama, Y.
An Intramolecular Disulfide Bridge as a Catalytic Switch for Serotonin N-Acetyltransferase
J. Biol. Chem.
277
44229-44235
2002
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Choi, B.H.; Chae, H.D.; Park, T.J.; Oh, J.; Lim, J.; Kang, S.S.; Ha, H.; Kim, K.T.
Protein kinase C regulates the activity and stability of serotonin N-acetyltransferase
J. Neurochem.
90
442-454
2004
Rattus norvegicus
Manually annotated by BRENDA team
Ferry, G.; Ubeaud, C.; Dauly, C.; Mozo, J.; Guillard, S.; Berger, S.; Jimenez, S.; Scoul, C.; Leclerc, G.; Yous, S.; Delagrange, P.; Boutin, J.A.
Purification of the recombinant human serotonin N-acetyltransferase (EC 2.3.1.87): further characterization of and comparison with AANAT from other species
Protein Expr. Purif.
38
84-98
2004
Ovis aries, Homo sapiens (Q16613), Homo sapiens, Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Tosini, G.; Chaurasia, S.S.; Michael Iuvone, P.
Regulation of arylalkylamine N-acetyltransferase (AANAT) in the retina
Chronobiol. Int.
23
381-391
2006
Macaca mulatta (O97756), Gallus gallus (P79774), Rattus norvegicus (Q64666), Rattus norvegicus Fischer (Q64666)
Manually annotated by BRENDA team
Ho, A.K.; Terriff, D.L.; Price, D.M.; Wloka, M.T.; Chik, C.L.
The role of inducible repressor proteins in the adrenergic induction of arylalkylamine-N-acetyltransferase and mitogen-activated protein kinase phosphatase-1 in rat pinealocytes
Endocrinology
148
743-751
2007
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Han, S.; Kim, T.D.; Ha, D.C.; Kim, K.T.
Rhythmic expression of adenylyl cyclase VI contributes to the differential regulation of serotonin N-acetyltransferase by bradykinin in rat pineal glands
J. Biol. Chem.
280
38228-38234
2005
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Koch, M.; Dehghani, F.; Habazettl, I.; Schomerus, C.; Korf, H.W.
Cannabinoids attenuate norepinephrine-induced melatonin biosynthesis in the rat pineal gland by reducing arylalkylamine N-acetyltransferase activity without involvement of cannabinoid receptors
J. Neurochem.
98
267-278
2006
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Huang, Z.; Deng, J.; Borjigin, J.
A novel H28Y mutation in LEC rats leads to decreased NAT protein stability in vivo and in vitro
J. Pineal Res.
39
84-90
2005
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Iuvone, P.M.; Tosini, G.; Pozdeyev, N.; Haque, R.; Klein, D.C.; Chaurasia, S.S.
Circadian clocks, clock networks, arylalkylamine N-acetyltransferase, and melatonin in the retina
Prog. Retin. Eye Res.
24
433-456
2005
Gallus gallus, Rattus norvegicus, Xenopus laevis
Manually annotated by BRENDA team
Lee, H.R.; Kim, T.D.; Kim, H.J.; Jung, Y.; Lee, D.; Lee, K.H.; Kim, D.Y.; Woo, K.C.; Kim, K.T.
Heterogeneous ribonucleoprotein R regulates arylalkylamine N-acetyltransferase synthesis via internal ribosomal entry site-mediated translation in a circadian manner
J. Pineal Res.
59
518-529
2015
Rattus norvegicus (Q64666)
Manually annotated by BRENDA team
Wadas, B.; Borjigin, J.; Huang, Z.; Oh, J.H.; Hwang, C.S.; Varshavsky, A.
Degradation of serotonin N-acetyltransferase, a circadian regulator, by the N-end rule pathway
J. Biol. Chem.
291
17178-17196
2016
Homo sapiens (Q16613), Homo sapiens, Rattus norvegicus (Q64666)
Manually annotated by BRENDA team