Information on EC 2.1.1.49 - amine N-methyltransferase

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The expected taxonomic range for this enzyme is: Eutheria

EC NUMBER
COMMENTARY hide
2.1.1.49
-
RECOMMENDED NAME
GeneOntology No.
amine N-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + an amine = S-adenosyl-L-homocysteine + a methylated amine
show the reaction diagram
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-
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-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
methyl group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
beta-alanine betaine biosynthesis
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nicotine degradation IV
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Tryptophan metabolism
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:amine N-methyltransferase
An enzyme of very broad specificity; many primary, secondary and tertiary amines can act as acceptors, including tryptamine, aniline, nicotine and a variety of drugs and other xenobiotics.
CAS REGISTRY NUMBER
COMMENTARY hide
51377-47-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
amine N-methyltransferase A
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-
Manually annotated by BRENDA team
Oryctolagus cuniculus New Zealand
strain New Zealand, 10-16 week old
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-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(R)-isosalsoline + methyl group donor
N-methyl-(R)-isosalsoline + demethylated methyl group donor
show the reaction diagram
-
-
N-methyl-(R)-isosalsoline is enzymatically formed in liver and can be transported into the brain from blood, it may act as neurotransmitter
?
S-adenosyl-L-methionine + 1,2,3,4-tetrahydroisoquinoline
S-adenosyl-L-homocysteine + N-methyl-1,2,3,4-tetrahydroisoquinoline
show the reaction diagram
-
amine N-methyltransferase A
-
?
S-adenosyl-L-methionine + 5-methyloxytryptamine
?
show the reaction diagram
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
?
show the reaction diagram
-
substrate with highest apparent kcat
-
-
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
show the reaction diagram
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
show the reaction diagram
S-adenosyl-L-methionine + aniline
?
show the reaction diagram
-
poor substrate
-
-
?
S-adenosyl-L-methionine + anisidine
?
show the reaction diagram
-
higher activity with transferase B
-
-
?
S-adenosyl-L-methionine + beta-phenylethylamine
?
show the reaction diagram
-
5-methyltetrahydrofolate can replace S-adenosyl-L-methionine as methyl donor
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-
?
S-adenosyl-L-methionine + desmethylimipramine
?
show the reaction diagram
S-adenosyl-L-methionine + imidazole
?
show the reaction diagram
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + isosalsoline
S-adenosyl-L-homocysteine + N-methylisosalsoline
show the reaction diagram
-
isosalsoline is identical with 7-hydroxy-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline, stereospecific N-methylation by amine N-methyltransferase A, (+)-(R)-enantiomer is preferentially methylated
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?
S-adenosyl-L-methionine + N-methylbutylamine
S-adenosyl-L-homocysteine + N,N-dimethylbutylamine
show the reaction diagram
-
only transferase A
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-
?
S-adenosyl-L-methionine + N-methylcyclohexylamine
S-adenosyl-L-homocysteine + N,N-dimethylcyclohexylamine
show the reaction diagram
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only transferase A
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-
?
S-adenosyl-L-methionine + N-methyltryptamine
S-adenosyl-L-homocysteine + N,N-dimethyltryptamine
show the reaction diagram
S-adenosyl-L-methionine + phenyltetrahydropyridine
?
show the reaction diagram
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + pyrazole
?
show the reaction diagram
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + salsolidine
S-adenosyl-L-homocysteine + N-methylsalsolidine
show the reaction diagram
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salsolidine is identical with 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline, stereospecific N-methylation by amine N-methyltransferase A, (-)-(S)-enantiomer is preferentially methylated
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?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
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
(R)-isosalsoline + methyl group donor
N-methyl-(R)-isosalsoline + demethylated methyl group donor
show the reaction diagram
-
-
N-methyl-(R)-isosalsoline is enzymatically formed in liver and can be transported into the brain from blood, it may act as neurotransmitter
?
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
N,N-Dimethyltryptamine
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competitive inhibitor
additional information
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substrate inhibition, but not by tryptamine and 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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biosynthesis of enzyme is induced in response to obstructive jaundice
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01 - 2
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
7.6 - 7.8
aniline
6.25
beta-phenylethylamine
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5-methyltetrahydrofolate as methyl donor
0.24 - 0.3
desmethylimipramine
0.2 - 5.1
imidazole
1.5 - 3.2
pyrazole
0.015
S-adenosyl-L-methionine
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1 mM tryptamine as methyl acceptor, pH 8.5
0.12 - 35.6
tryptamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.667 - 3.67
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
0.0333 - 0.367
aniline
0.233
desmethylimipramine
Oryctolagus cuniculus
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transferase A, pH 8.5
0.0833 - 0.167
imidazole
0.1 - 0.25
pyrazole
0.117 - 0.2
S-adenosyl-L-methionine
0.4 - 0.45
tryptamine
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.006 - 0.01
N,N-Dimethyltryptamine
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00000038
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beta-phenylethylamine + S-adenosyl-L-methionine
0.00000118
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tryptamine + S-adenosyl-L-methionine
0.0000012
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N-methyltransferase A, (-)-(S)-isosalsoline
0.0000021
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N-methyltransferase A, (-)-(S)-salsolidine
0.0000033
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N-methyltransferase A, (+)-(R)-isosalsoline
0.000065
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beta-phenylethylamine + 5-methyltetrahydrofolate
0.000068
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N-methyltransferase A, aniline
0.000198
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tryptamine + 5-methyltetrahydrofolate
0.00022
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N-methyltransferase B, desmethylimipramine
0.00026
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N-methyltransferase A, desmethylimipramine
0.00044
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N-methyltransferase A, tryptamine
0.00127
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N-methyltransferase B, aniline
0.0031
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N-methyltransferase B, tryptamine
additional information
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specific activities of serum, control and cholestatic liver in cytosolic, mitochondrial and microsomal preparations for 0.5, 1, 2, 3, 7, 14, 28 and 42 days after common bile duct ligation, activities of mitochondrial and microsomal enzyme in cholestatic liver and of serum enzyme increase after common bile duct ligation, Vmax-values
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
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5-methyltetrahydrofolate as donor
7.9
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S-adenosyl-L-methionine as donor
additional information
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transferase A: pI 4.9, transferase B: pI 5.1
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2 - 8.9
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tryptamine, about half-maximal activity at pH 7.2 and 8.9, transferase A
7.5 - 8.8
-
tryptamine, about half-maximal activity at pH 7.5 and 90% at pH 8.8, transferase B
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
investigation of enzyme in serum, after common bile duct ligation for a period of 42 days
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
hepatic membrane-bound enzyme
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
-
gel filtration
additional information
-
amino acid composition of transferase A
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
-
optimal for transferase A
441354
7.8
-
optimal for transferase B
441354
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80°C, partially purified, per month, less than 10% loss of activity
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-80°C, purified, per month, about 25% loss of activity
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2°C, per week, 25% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
amine N-methyltransferase A
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two N-methyltransferases A and B separable by ammonium sulfate fractionation, HPLC-ion exchange chromatography
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