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 ACCESSION NO.
LITERATURE
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 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
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
methyl group transfer
-
-
-
-
O-methylation
-
-
-
-
PATHWAY
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 ACCESSION NO.
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
SEQUENCE CODE
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 ACCESSION NO.
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 ACCESSION NO.
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 ACCESSION NO.
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 ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
Arginine vasotocin
-
-
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
-
-
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
additional information
-
not inhibitory: dexamethasone
-
additional information
-
not inhibitory: (2S,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
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]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
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]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.042
-
N-acetylserotonin
-
-
0.0059
-
pyridoxal 5'-phosphate
-
S-adenosylmethionine
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
enzyme assay
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
8.3
-
-
7.9
8.4
-
-
7.9
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.8
8.4
-
-
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
assay at
37
-
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
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
-
highest activity in liver
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
additional information
-
not: liver, kidney, heart, lung, adrenal gland, pancreas, salivary gland, skin
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
76000
78000
-
-
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
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 ACCESSION NO.
LITERATURE
immobilized metal ion affinity chromatography (Ni2+)
-, P46597
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
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
-