Information on EC 2.1.1.4 - acetylserotonin O-methyltransferase

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The expected taxonomic range for this enzyme is: Euteleostomi

EC NUMBER
COMMENTARY
2.1.1.4
-
RECOMMENDED NAME
GeneOntology No.
acetylserotonin O-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
reaction sequence is ordered bi-bi type
-
S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
reaction sequence is ordered bi-bi type
-
S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
addition of S-adenosyl-L-methionine occuring first followed by N-acetylserotonin
-
S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
addition of S-adenosyl-L-methionine occuring first followed by N-acetylserotonin
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
-
-
-
-
O-methylation
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
serotonin and melatonin biosynthesis
-
-
Tryptophan metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:N-acetylserotonin O-methyltransferase
Some other hydroxyindoles also act as acceptor, but more slowly.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
acetylserotonin methyltransferase
-
-
-
-
ASMT
-
-
-
-
HIOMT
-
-
-
-
HIOMT
-
-
HIOMT
Rattus norvegicus Wistar
-
-
-
hydroxindole-O-methyltransferase
-
-
hydroxyindole methyltransferase
-
-
-
-
hydroxyindole O-methyltransferase
-
-
-
-
hydroxyindole-O-methyl transferase
-
-
-
-
hydroxyindole-O-methyltransferase
-
isoenzyme 2
hydroxyindole-O-methyltransferase
-
-
hydroxyindole-O-methyltransferase
-
-
hydroxyindole-O-methyltransferase
-
-
hydroxyindole-O-methyltransferase
P46597
-
hydroxyindole-O-methyltransferase
-
-
methyltransferase, acetylserotonin
-
-
-
-
N-acetylserotonin O-methyltransferase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9029-77-0
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
black rhinoceros
-
-
Manually annotated by BRENDA team
Frog
-
-
-
Manually annotated by BRENDA team
tissues and Y79 retinoblastoma cells
-
-
Manually annotated by BRENDA team
Y79 retinoblastoma cells
-
-
Manually annotated by BRENDA team
monkey
-
-
Manually annotated by BRENDA team
rainbow trout
-
-
Manually annotated by BRENDA team
Chinook salmon
-
-
Manually annotated by BRENDA team
Rattus norvegicus Wistar
Wistar
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
HIOMT is a key enzyms involved in melatonin synthesis
metabolism
-
last enzyme of the melatonin-synthesis pathway
physiological function
-
HIOMT is required for full transcriptional activation in chicken embryonic retinal cells
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-hydroxy-N-acetyltryptamine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-4-methoxytryptamine
show the reaction diagram
-
8% of the activity with N-acetylserotonin
-
-
?
5-hydroxyindoleacetic acid + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 5-methoxyindoleacetic acid
show the reaction diagram
-
12% of the activity with N-acetylserotonin
-
-
?
bufotenine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N,N-dimethyl-5-hydroxytryptamine
show the reaction diagram
-
-
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-methylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-methyl-5-methoxytryptamine
show the reaction diagram
-
9% of the activity with N-acetylserotonin
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
Frog
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
-
the enzyme is involved in melatonin biosynthesis in egg yolk, overview
-
-
?
serotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
serotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + 5-methoxytryptamine
show the reaction diagram
-
7% of the activity with N-acetylserotonin
-
-
?
bufotenine + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N,N-dimethyl-5-hydroxytryptamine
show the reaction diagram
-
14% of the activity with N-acetylserotonin
-
-
?
additional information
?
-
-
absolute requirement for S-adenosylmethionine
-
-
-
additional information
?
-
-
activity is controlled by the endogenous clock
-
-
-
additional information
?
-
-
bovine enzyme has high specificity towards N-acetylserotonin, chicken enzyme methylates N-acetylserotonin and to some extent serotonin and bufotenine
-
-
-
additional information
?
-
Rattus norvegicus, Rattus norvegicus Wistar
-
in pineal glands isolated in the morning 4 h magnetic field exposure changes melatonin release by affecting the signal transduction pathway leading from the norepinephrine receptor to N-acetyltransferase and hydroxyindole-O-methyltransferase and not via a direct effect at the enzyme levels
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
-
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
N-acetylserotonin + S-adenosyl-L-methionine
S-adenosyl-L-homocysteine + N-acetyl-5-methoxytryptamine
show the reaction diagram
-
formation of the hormone melatonin
-
-
?
S-adenosyl-L-methionine + N-acetylserotonin
S-adenosyl-L-homocysteine + melatonin
show the reaction diagram
-
the enzyme is involved in melatonin biosynthesis in egg yolk, overview
-
-
?
additional information
?
-
Rattus norvegicus, Rattus norvegicus Wistar
-
in pineal glands isolated in the morning 4 h magnetic field exposure changes melatonin release by affecting the signal transduction pathway leading from the norepinephrine receptor to N-acetyltransferase and hydroxyindole-O-methyltransferase and not via a direct effect at the enzyme levels
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Arginine vasotocin
-
-
Ca2+
-
-
Cu2+
-
-
cysteamine
-
rat enzyme inhibited to 50% at 0.128 mM, bovine and ovine enzyme not
cysteic acid
-
-
glutathione
-
-
Homocysteic acid
-
-
L-glutamate
-
inhibition is reversible, dose-dependent, no inhibition of mRNA expression
N-acetylserotonin
-
-
N-acetylserotonin
-
activation
N-acetylserotonin
-
-
N-acetylserotonin
-
-
Oxytocin
-
-
p-chloromercuribenzoate
-
-
pyridoxal 5'-phosphate
-
-
S-adenosyl-L-homocysteine
-
-
S-adenosyl-L-homocysteine
-
-
S-adenosyl-L-homocysteine
-
-
S-adenosyl-L-methionine
-
-
S-adenosyl-L-methionine
-
activation
Selenocysteamine
-
50% inhibition at 0.013 mM
Vasopressin
-
-
Mg2+
-
-
additional information
-
not inhibitory: dexamethasone
-
additional information
-
not inhibitory: (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
N-acetylserotonin
-
inhibition
N-acetylserotonin
-
activation
oxaloacetate
-
activation
S-adenosyl-L-methionine
-
inhibition
S-adenosyl-L-methionine
-
activation
bicarbonate
-
activation
additional information
-
citric acid cycle intermediates are good activators
-
additional information
-
retinoic acid stereoisomers induce an increase in activity and mRNA level
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005
N-acetylserotonin
-
-
0.015
N-acetylserotonin
-
-
0.0291
N-acetylserotonin
-
-
0.04
N-acetylserotonin
-
-
0.054
N-acetylserotonin
-
-
0.1
N-acetylserotonin
-
-
0.005
S-adenosyl-L-methionine
-
-
0.00856
S-adenosyl-L-methionine
-
-
0.04
S-adenosyl-L-methionine
-
-
0.046
S-adenosyl-L-methionine
-
-
0.11
S-adenosyl-L-methionine
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.042
N-acetylserotonin
-
-
0.0059
pyridoxal 5'-phosphate
-
S-adenosylmethionine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
enzyme assay
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5 - 8.3
-
-
7.9 - 8.4
-
-
7.9
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.8 - 8.4
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
-
assay at
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Frog
-
low activity
Manually annotated by BRENDA team
-
fertile egg yolk
Manually annotated by BRENDA team
-
no activity in early embryos
Manually annotated by BRENDA team
-
postovulatory, no activity in preovulatory ovarian follicle
Manually annotated by BRENDA team
-
CD19+ cell, CD14-CD4+ cell, CD56-CD8+ cell, CD56+ cell
Manually annotated by BRENDA team
-
not surrounding areas
Manually annotated by BRENDA team
P46597
pineal parenchymal cell tumor
Manually annotated by BRENDA team
Rattus norvegicus Wistar
-
-
-
Manually annotated by BRENDA team
Frog
-
-
Manually annotated by BRENDA team
-
very low levels
Manually annotated by BRENDA team
-
embryonic retina
Manually annotated by BRENDA team
-
lowest activity in spleen
Manually annotated by BRENDA team
-
mucosa from the ulcer margin
Manually annotated by BRENDA team
-
highest activity in liver
Manually annotated by BRENDA team
additional information
-
not: liver, kidney, heart, lung, adrenal gland, pancreas, salivary gland, skin
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
76000 - 78000
-
-
441483
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 38000, SDS-PAGE
?
-
x * 38000, SDS-PAGE
?
-
x * 42000, SDS-PAGE
dimer
-
2 * 39000, SDS-PAGE
polymer
-
x * 21800
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 96 h, pineal enzyme stable
-
frozen, stable for several weeks
-
4°C, 96 h, pineal enzyme stable
-
4°C, 96 h, inactivated
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
immobilized metal ion affinity chromatography (Ni2+)
P46597
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene sequenced
-
expression analysis in eggs
-
expressed in HEK-293 cells
-
FreeStyle 293 expression system used for cellular expression, His-tagged protein synthesized in the Rapid translation system RTS500
P46597
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
significant daily rhythms of mRNA in pineal gland, liver and hindgut
-
In retinal cells the mutation of the YY1-binding site decreases the HIOMT promoter activity by 70%
-
the rat Crx transcription factor is able to activate the HIOMT promoter in transfected HEK-293 cells
-
there is an age-related decline in rat extrapineal melatonin synthesis with a consequent HIOMT functionality decrease in spleen, liver and heart during physiological aging, in the thymus HIOMT expression reveals no significant alterations with age
-
the mRNA expression for HIOMT is only slightly increased at day 0 upon ulcer induction when compared with that in the intact mucosa, but at day 8 after ulcer formation, this expression of HIOMT is significantly enhanced, particularly at the ulcer areas in rats treated with melatonin or L-tryptophan
-
the expression level in submandibular gland is higher in the dark period compared with the light period
-