Information on EC 2.1.1.28 - phenylethanolamine N-methyltransferase

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The expected taxonomic range for this enzyme is: Euteleostomi

EC NUMBER
COMMENTARY hide
2.1.1.28
-
RECOMMENDED NAME
GeneOntology No.
phenylethanolamine N-methyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + phenylethanolamine = S-adenosyl-L-homocysteine + N-methylphenylethanolamine
show the reaction diagram
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
catecholamine biosynthesis
Metabolic pathways
-
-
noradrenaline and adrenaline degradation
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-
Tyrosine metabolism
-
-
SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:phenylethanolamine N-methyltransferase
Acts on various phenylethanolamines; converts noradrenaline into adrenaline.
CAS REGISTRY NUMBER
COMMENTARY hide
9037-68-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57BL/6 mice
-
-
Manually annotated by BRENDA team
-
-
-
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
2-hydroxyphenylethanolamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
i.e. o-octopamine
-
-
?
3,4-dichlorophenyl ethanolamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
3,4-dichlorophenylethanolamine + S-adenosyl-L-methionine
N-methyl-3,4-dichlorophenylethanolamine + S-adenosyl-L-homocysteine
show the reaction diagram
3,4-dichlorophenylethylenediamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
3,4-dihydroxynorephedrine + S-adenosyl-L-methionine
3,4-dihydroxyephedrine + S-adenosyl-L-homocysteine
show the reaction diagram
-
18% of the activity with normetanephrine
-
-
?
3-chloro-4-hydroxyphenylethanolamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
3-hydroxyphenylethanolamine + S-adenosyl-L-methionine
N-methyl-m-octopamine + S-adenosyl-L-homocysteine
show the reaction diagram
3-trifluoromethylphenylethanolamine + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
?
3-trifluoromethylphenylethanolamine + S-adenosyl-L-methionine
N-methyl-3-trifluoromethylphenylethanolamine + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
4-hydroxynorephedrine + S-adenosyl-L-methionine
4-hydroxyephedrine + S-adenosyl-L-homocysteine
show the reaction diagram
-
18% of the activity with normetanephrine
-
-
?
4-hydroxyphenylethanolamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
i.e. octopamine
-
-
?
9-methylnorharman + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
anti-9-amino-6-(trifluoromethyl)benzonorbornene + S-adenosyl-L-methionine
?
show the reaction diagram
-
-
-
?
cis-(1R,2S)-2-amino-1-tetralol + S-adenosyl-L-methionine
cis-(1R,2S)-2-methylamino-1-tetralol + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
D-norepinephrine + S-adenosyl-L-methionine
epinephrine + S-adenosyl-L-homocysteine
show the reaction diagram
DL-m-hydroxyphenylethanolamine + S-adenosyl-L-methionine
neosynephrine + S-adenosyl-L-homocysteine
show the reaction diagram
-
60% of the activity with normetanephrine
-
-
?
DL-neo-synephrine + S-adenosyl-L-methionine
3-hydroxy-alpha-[(dimethylamine)methyl]benzenemethanol + S-adenosyl-L-homocysteine
show the reaction diagram
-
20% of the activity with normetanephrine
-
-
?
DL-octopamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
18% of the activity with normetanephrine
-
-
?
dopamine + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
epinephrine + S-adenosyl-L-methionine
? + D-adenosylhomocysteine
show the reaction diagram
-
-
-
-
?
L-norephedrine + S-adenosyl-L-methionine
ephedrine + S-adenosyl-L-homocysteine
show the reaction diagram
-
14% of the activity with normetanephrine
-
-
?
L-norepinephrine + S-adenosyl-L-methionine
epinephrine + S-adenosyl-L-homocysteine
show the reaction diagram
norepinephrine + S-adenosyl-L-methionine
epinephrine + S-adenosyl-L-homocysteine
show the reaction diagram
normetanephrine + S-adenosyl-L-methionine
metanephrine + S-adenosyl-L-homocysteine
show the reaction diagram
octopamine + S-adenosyl-L-methionine
N-methyloctopamine + S-adenosyl-L-homocysteine
show the reaction diagram
-
-
-
-
?
phenylethanolamine + S-adenosyl-L-methionine
N-methylphenylethanolamine + S-adenosyl-L-homocysteine
show the reaction diagram
S-adenosyl-L-methionine + 4-aminomethyl-1,2,3,4-tetrahydroisoquinoline
S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
-
-
?
S-adenosyl-L-methionine + noradrenaline
S-adenosyl-L-homocysteine + epinephrine
show the reaction diagram
-
-
-
-
?
S-adenosyl-L-methionine + norepinephrine
S-adenosyl-L-homocysteine + epinephrine
show the reaction diagram
S-adenosyl-L-methionine + phenylethanolamine
S-adenosyl-L-homocysteine + N-methylphenylethanolamine
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
9-methylnorharman + S-adenosyl-L-methionine
? + S-adenosyl-L-homocysteine
show the reaction diagram
-
PNMT catalyzes the 2N-methylation of beta-carbolines, forming 2N-methylated beta-carbolinium cations, which are structural and functional analogs of the Parkinsonian-inducing toxin MPP+
-
-
?
S-adenosyl-L-methionine + norepinephrine
S-adenosyl-L-homocysteine + epinephrine
show the reaction diagram
S-adenosyl-L-methionine + phenylethanolamine
S-adenosyl-L-homocysteine + N-methylphenylethanolamine
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
S-adenosyl-L-methionine
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(6R)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
(6R)-6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
-
(6S)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
(6S)-6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
-
(7-nitro-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol
-
-
(R)-3-methyl-1,2,3,4-tetrahydroisoquinoline
-
-
(R)-7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
-
-
(S)-3-methyl-1,2,3,4-tetrahydroisoquinoline
-
-
1,2,3,4-tetrahydrobenz[h]isoquinoline
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid
-
-
1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
1,4-diaminonaphthalene-2,6-disulfonic acid
-
-
1-(2,3-dichlorophenyl)ethanamine
-
-
1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)ethanone
-
-
1-aminoisoquinoline
-
Kd: 14 microM
1-phenylmethanamine
-
-
1-thiophen-2-ylmethanamine
-
-
1-thiophen-3-ylmethanamine
-
-
2,3,4,5-tetrahydro-1H-2-benzazepine
-
-
2,3,4,5-tetrahydro-5H-1,4-benzodiazepine
-
-
2,3,4,5-tetrahydro-5H-1,4-benzothiazepine
-
-
2,3,4,5-tetrahydro-5H-1,4-benzoxazepine
-
-
2,3-dichloro-alpha-methylbenzylamine
-
2,5-Dimethyl-1-aminobenzimidazole
2-amino-1-methylbenzimidazole
-
Kd: 4.6 microM
2-amino-4(7)-hydroxy-benzimidazole
-
Kd: 20 microM
2-amino-5(6)-chloro-7(4)-hydroxy-benzimidazole
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Kd: 14 microM
2-amino-5(6)-chloro-benzimidazole
-
Kd: 1.8 microM
2-amino-5(6)-fluoro-benzimidazole
-
Kd: 7.2 microM
2-aminobenzimidazole
-
Kd: 6.3 microM
2-Aminotetralin
-
most effective inhibitor
2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
2-bromo-6-(trifluoromethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
2-chlorophenylethanolamine
-
-
2-fluorophenylethanolamine
-
-
2-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
2-phenylethanamine
-
-
2-Phenylethylamine
-
-
2-thiophen-2-ylethanamine
-
-
3,4-dichloroamphetamine
3,4-Dichlorophenylethanolamine
3,4-dichlorophenylethylenediamine
-
substrate inhibition
3,4-dihydroxyphenylethanolamine
-
-
3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
very high selectivity
3-(fluoromethyl)-7-(thiomorpholin-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-(fluoromethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline
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high selectivity
3-(fluoromethyl)-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
very high selectivity
3-(fluoromethyl)-N-(3,3,3-trifluoropropyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
-
3-(trifluoromethyl)-1,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine
-
-
3-bromophenylethanolamine
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-
3-butyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-(ethylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-(N-2,2,2-trifluoroethylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-(N-3-methoxypropylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-(N-4-nitrophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-(propylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-iodo-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-methylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
-
3-difluoromethyl-7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-ethyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
moderate selectivity
3-ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
moderate selectivity
3-ethyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
moderate selectivity
3-fluoromethyl-7-(2,2,2-trifluoroethylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-(3,3,3-trifluoropropylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-(4,4,4-trifluorobutylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-(4-chlorobenzylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-(N-benzylaminosulfonyl)-1,2,3,4-tetrahydrosioquinoline
-
-
3-fluoromethyl-7-(N-methylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-aminosulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-azido-1,2,3,4-tetrahydrosioquinoline
-
-
3-fluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-iodo-1,2,3,4-tetrahydroisoquinoline
3-fluoromethyl-7-isothiocyanato-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-methanesulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-propylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-fluoromethyl-7-[N-(4-chlorophenyl)aminosulfonyl]-1,2,3,4-tetrahydroisoquinoline
-
-
3-hydroxyethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
3-hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
3-hydroxymethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
high selectivity
3-hydroxypropyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
extension of the 3-hydroxyalkyl chain by just one carbon results in a significant loss in phenylethanolamine N-methyltransferse inhibitory potency
3-hydroxypropyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
3-isopropyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
3-methyl-1,2,3,4-tetrahydroisoquinoline
3-methyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
high selectivity
3-methyl-1,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine
-
-
3-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
3-methyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
high selectivity
3-Phenylpropylamine
-
-
3-propyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
high selectivity
3-propyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
moderate selectivity
3-thienylmethylamine
-
inhibits the enzyme and is selective toward the alpha2-adrenoceptor
3-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
3-trifluoromethyl-1,2,3,4-tetrahydroisoquinolines
-
several 3-trifluoromethyl-1,2,3,4-tetrahydroisoquinolines and some enantiomers of 3-trifuoromethyl-1,2,3,4-tetrahydroisoquinolines. For the phenylethanolamine N-methyltransferase inhibitory potency of different 3-trifuoromethyl-1,2,3,4-tetrahydroisoquinolines, compounds bearing a lipophilic 7-substituent show higher potency than compounds bearing a hydrophilic 7-substituent. Comparison to the inhibitory activity of the entantiomers of the most potent racemates show that the R-enantiomers are approximately 4fold as potent as their corresponding S-enantiomers.
-
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
3-trifluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
-
3-trifluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
-
4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
-
4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide
-
-
4-(benzo[d][1,3]dioxol-5-ylamino)-4-oxobutanoic acid
-
-
4-bromo-1H-imidazole
-
Kd: 170 microM
4-bromophenylethanolamine
-
-
4-fluorophenylethanolamine
-
-
4-hydroxyphenylethanolamine
-
-
4-oxo-1,4-dihydroquinoline-3,7-dicarboxylic acid
-
-
4-quinolinol
-
Kd: 690 microM
5,6-Dichloro-2-aminotetralin
-
0.00093 mM, 50% inhibition, competitive with norepinephrine as substrate
5-chlorobenzimidazole
-
Kd: 97 microM
6-(trifluoromethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
6-Aminoquinoline
-
Kd: 380 microM
6-Chloropurine
-
Kd: 140 microM
6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
-
6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
-
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
7-(3-methoxypropylsulfonyl)-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-(N-4-chlorophenylaminosulfonyl)-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-(N-butylaminosulfonyl)-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-acetamido-1,2,3,4-tetrahydroisoquinoline
-
-
7-allylsulfonyl-1,2,3,4-tetrahydrosioquinoline
-
-
7-aminocarbonyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-aminomethyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride
-
-
7-aminosulfonyl-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
7-aminosulfonyl-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-aminosulfonyl-1,2,3,4-tetrahydroisoquinoline
-
i.e. SK&F 29661
7-aminosulfonyl-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-benzoyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-benzyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-bromo-1,2,3,4-tetrahydrobenzo[h]isoquinoline
-
7-bromo-1,2,3,4-tetrahydroben[h]isoquinoline is 2fold more potent as an inhibitor of phenylethanolamine N-methyltransferase than 1,2,3,4-tetrahydroben[h]isoquinoline.
7-bromo-1,2,3,4-tetrahydrobenz[h]isoquinoline
7-bromo-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-bromo-1,2,3,4-tetrahydroisoquinoline
7-bromo-3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline
-
high selectivity
7-bromo-3-butyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-3-ethyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-3-hydroxyethyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
-
moderate selectivity
7-bromo-3-hydroxypropyl-1,2,3,4-tetrahydroisoquinoline
-
little selcetivity
7-bromo-3-isopropyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline
7-bromo-3-pentyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-3-propyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-bromo-N-triphenylmethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-butylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-cyano-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
7-cyano-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-ethylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-hydroxy-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
7-hydroxy-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline oxalate
-
-
7-iodo-1,2,3,4-tetrahydroisoquinoline
7-methoxy-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
7-methoxy-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-methylsulfinyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-methylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-methylsulfonyl-3-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-methylthio-1,2,3,4-tetrahydroisoquinoline
-
-
7-nitro-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
7-nitro-1,2,3,4-tetrahydrobenz[h]isoquinoline hydrochloride
7-nitro-1,2,3,4-tetrahydroisoquinoline
7-nitro-3-pentyl-1,2,3,4-tetrahydroisoquinoline
-
little selectivity
7-nitro-3-propyl-1,2,3,4-tetrahydroisoquinoline
-
moderate selectivity
7-phenylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-sulfonamido-1,2,3,4-tetrahydroisoquinoline
-
-
7-trichloromethylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline
-
-
7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
8,9-dichloro-2,3,4,5-tetrahydro-1H-2-benzazepine
adenine
-
Kd: 180 microM
benzylamine
-
-
D-norepinephrine
-
substrate inhibition
dopamine
-
competitive inhibition with respect to phenylethanolamine
epinephrine
human cerebrospinal fluid
-
-
-
L-norepinephrine
-
substrate inhibition
LY134046
methanol
-
at nonsaturating concentrations of phenylethanolamine, methanol inhibits in a competitive fashion. With respect to S-adenosyl-L-methionine inhibition by methanol is noncompetitive
N-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
-
N-(4-chlorophenyl)-3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
-
N-(4-chlorophenyl)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
-
norepinephrine
octopamine
-
at high concentrations
p-hydroxymercuribenzoate
-
0.00001 mM, 75% loss of activity
phenylethanolamine
-
at high concentrations
Phenylethylamine
-
competitive inhibition with respect to phenylethanolamine
R-(+)-7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
-
-
S-adenosyl-L-methionine
S-adenosylhomocysteine
sinefungin
-
-
SK&F 29661
-
-
SKF 29661
SKF 64139
1,2,3,4-tetrahydroisoquinoline derivate with two chloro substituents on the aromatic ring. Is able to cross the blood-brain barrier.
trans-(1S,2S)-2-amino-1-tetralol
-
-
tyramine
-
at high concentrations
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.676
2-hydroxyphenylethanolamine
-
-
0.0008 - 0.00159
3,4-Dichlorophenylethanolamine
0.012 - 0.0131
3,4-dichlorophenylethylenediamine
0.013
3,4-dihydroxyphenylethanolamine
-
-
0.0024
3-chloro-4-hydroxyphenylethanolamine
-
-
0.089
3-hydroxyphenylethanolamine
-
-
0.366
3-methoxy-4-hydroxy-phenylethanolamine
-
-
0.00054 - 0.055
3-trifluoromethylphenylethanolamine
0.047
4-aminomethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.017
4-hydroxyphenylethanolamine
-
-
0.0015 - 0.025
anti-9-amino-6-(trifluoromethyl)benzonorbornene
0.0053
cis-(1R,2S)-2-amino-1-tetralol
-
wild type enzyme, assay mixture consists of 25 microl of 0.5 M phosphate buffer (pH 8.0), 5 microl of [methyl-3H]S-adenosyl-L-methionine containing approximately 2.5 X 10 00000 dpm, varying amounts of phenylethanolamine and unlabeled S-adenosyl-L-methionine, 20 microl enzyme and water at 30C.
0.0297 - 0.109
D-norepinephrine
0.015 - 0.101
L-norepinephrine
0.089
m-octopamine
-
-
0.0184
norepinephrine
-
wild-type enzyme
0.05
normetanephrine
-
-
0.0055
octopamine
0.07 - 2.05
phenylethanolamine
0.0012 - 0.045
S-adenosyl-L-methionine
additional information
additional information
-
Km-value of mutant enzymes
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.001 - 0.0083
3-trifluoromethylphenylethanolamine
0.0043 - 0.0062
anti-9-amino-6-(trifluoromethyl)benzonorbornene
0.0048
cis-(1R,2S)-2-amino-1-tetralol
Homo sapiens
-
wild type enzyme, assay mixture consists of 25 microl of 0.5 M phosphate buffer (pH 8.0), 5 microl of [methyl-3H]S-adenosyl-L-methionine containing approximately 2.5 X 10 00000 dpm, varying amounts of phenylethanolamine and unlabeled S-adenosyl-L-methionine, 20 microl enzyme and water at 30C.
0.02 - 0.021
octopamine
0.00017 - 0.0483
phenylethanolamine
0.0017 - 0.0658
S-adenosyl-L-methionine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15.5
3-trifluoromethylphenylethanolamine
Homo sapiens
-
pH 8.0, 30C
18257
3.67
octopamine
Homo sapiens
-
pH 8.0, 30C
1759
0.467
phenylethanolamine
Homo sapiens
-
pH 8.0, 30C
2578
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0096
(6R)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
R-isomer, pH 8.0, 37C
0.15
(6R)-6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
R-isomer, pH 8.0, 37C
0.00031
(6S)-6-methyl-2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
S-isomer, pH 8.0, 37C
0.0033
(6S)-6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
S-isomer, pH 8.0, 37C
0.000017 - 0.000145
(7-nitro-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol
0.0383
(R)-3-methyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00101
(S)-3-methyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00049
1,2,3,4-tetrahydrobenz[h]isoquinoline
0.0058
1,2,3,4-tetrahydroisoquinoline
0.47
1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid
-
-
0.00012 - 0.0069
1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
0.00009
1-(2,3-dichlorophenyl)ethanamine
-
pH 8.0
0.061
1-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl)ethanone
-
pH 8.0, 37C
0.45
1-thiophen-2-ylmethanamine
-
pH 8.0, 37C
0.11
1-thiophen-3-ylmethanamine
-
pH 8.0, 37C
0.00334
2,3,4,5-tetrahydro-1H-2-benzazepine
-
-
0.028
2,3,4,5-tetrahydro-5H-1,4-benzodiazepine
-
-
0.0041
2,3,4,5-tetrahydro-5H-1,4-benzothiazepine
-
-
0.0212
2,3,4,5-tetrahydro-5H-1,4-benzoxazepine
-
-
0.000072 - 0.00133
2,3-dichloro-alpha-methylbenzylamine
0.0012
2-bromo-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.00073 - 0.021
2-bromo-6-(trifluoromethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
0.025
2-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.0026
2-nitro-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.22
2-Phenylethylamine
-
pH 8.0, 37C
0.3
2-thiophen-2-ylethanamine
-
pH 8.0, 37C
0.00227 - 0.0148
3,4-dichloroamphetamine
0.508 - 0.909
3,4-Dichlorophenylethanolamine
1.138 - 1.522
3,4-dichlorophenylethylenediamine
0.00082
3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00015
3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.0000018 - 0.000315
3-(fluoromethyl)-7-(thiomorpholin-4-ylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
0.00015
3-(fluoromethyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00013
3-(fluoromethyl)-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.000017 - 0.000035
3-(fluoromethyl)-N-(3,3,3-trifluoropropyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
0.017
3-(trifluoromethyl)-1,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.0066
3-butyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.0034
3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0032
3-difluoromethyl-7-(ethylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.00025
3-difluoromethyl-7-(N-2,2,2-trifluoroethylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0053
3-difluoromethyl-7-(N-3-methoxypropylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.037
3-difluoromethyl-7-(N-4-nitrophenylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0021
3-difluoromethyl-7-(propylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.000094
3-difluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0031
3-difluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0002
3-difluoromethyl-7-iodo-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.006
3-difluoromethyl-7-methylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.00017
3-difluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.000067
3-difluoromethyl-7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0018
3-ethyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.00049
3-ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00051
3-ethyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.0014
3-fluoromethyl-7-(2,2,2-trifluoroethylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.0013
3-fluoromethyl-7-(3,3,3-trifluoropropylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.067
3-fluoromethyl-7-(4,4,4-trifluorobutylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.032
3-fluoromethyl-7-(4-chlorobenzylsulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.0065
3-fluoromethyl-7-(N-benzylaminosulfonyl)-1,2,3,4-tetrahydrosioquinoline
-
-
0.0024
3-fluoromethyl-7-(N-methylaminosulfonyl)-1,2,3,4-tetrahydroisoquinoline
-
-
0.00066
3-fluoromethyl-7-aminosulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.0017
3-fluoromethyl-7-azido-1,2,3,4-tetrahydrosioquinoline
-
-
0.00064
3-fluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
0.0011
3-fluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
-
0.000073 - 0.00021
3-fluoromethyl-7-iodo-1,2,3,4-tetrahydroisoquinoline
0.00057
3-fluoromethyl-7-isothiocyanato-1,2,3,4-tetrahydroisoquinoline
-
-
0.0016
3-fluoromethyl-7-methanesulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.54
3-fluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
-
0.0024
3-fluoromethyl-7-propylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.00032
3-fluoromethyl-7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00074
3-fluoromethyl-7-[N-(4-chlorophenyl)aminosulfonyl]-1,2,3,4-tetrahydroisoquinoline
-
-
0.00035
3-hydroxyethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
0.00051
3-hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
0.000047
3-hydroxymethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0
0.0017
3-hydroxypropyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
0.0014
3-hydroxypropyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
0.0046
3-isopropyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.0014
3-methyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.000077
3-methyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.000067
3-methyl-1,2,3,4-tetrahydro[1]benzothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.000072
3-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.000034
3-methyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.00012
3-propyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.00092
3-propyl-N-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
-
pH 8.0, 37C
0.015
3-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00052
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
-
-
0.013
3-trifluoromethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline
-
-
0.002
3-trifluoromethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
-
0.037
4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.015
4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbonitrile
-
pH 8.0, 37C
0.1
4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide
-
pH 8.0, 37C
0.00027
5,6-Dichloro-2-aminotetralin
-
-
0.04
6-(trifluoromethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.0058
6-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine
-
pH 8.0, 37C
0.0000016 - 0.0000031
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
0.072
7-(3-methoxypropylsulfonyl)-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamnie as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.0009
7-(N-4-chlorophenylaminosulfonyl)-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0056
7-(N-butylaminosulfonyl)-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.19
7-acetamido-1,2,3,4-tetrahydroisoquinoline
-
-
0.0098
7-allylsulfonyl-1,2,3,4-tetrahydrosioquinoline
-
-
0.064
7-aminocarbonyl-1,2,3,4-tetrahydroisoquinoline
-
-
1.9
7-aminomethyl-1,2,3,4-tetrahydroisoquinoline dihydrochloride
-
-
0.033
7-aminosulfonyl-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
0.00068
7-aminosulfonyl-3-difluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
radiochemical assay, inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate, and three concentrations of inhibitor
0.0029
7-benzoyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.061
7-benzyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00022
7-bromo-1,2,3,4-tetrahydrobenzo[h]isoquinoline
0.000056
7-bromo-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.000023
7-bromo-3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.0076
7-bromo-3-butyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00048
7-bromo-3-ethyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00035
7-bromo-3-hydroxyethyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0
0.000012
7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0
0.0017
7-bromo-3-hydroxypropyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0
0.0044
7-bromo-3-isopropyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.000017
7-bromo-3-methyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.011
7-bromo-3-pentyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00048
7-bromo-3-propyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00029
7-bromo-N-triphenylmethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.018
7-butylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determined using four concentrations of phenylethanolamine as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.0023
7-cyano-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
0.014
7-ethylsulfonyl-3-fluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
inhibition constants are determine using four concentrations of phenylethanolamnie as the variable substrate and three concentrations of inhibitor with a radiochemical assay.
0.00091
7-hydroxy-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
0.011
7-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline oxalate
-
-
0.00004 - 0.00074
7-iodo-1,2,3,4-tetrahydroisoquinoline
0.0021
7-methoxy-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
0.0067
7-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.045
7-methylsulfinyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.0013
7-methylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.036
7-methylsulfonyl-3-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00061
7-methylthio-1,2,3,4-tetrahydroisoquinoline
-
-
0.0009
7-nitro-1,2,3,4-tetrahydrobenz[h]isoquinoline
-
-
0.00004 - 0.067
7-nitro-1,2,3,4-tetrahydroisoquinoline
0.0098
7-nitro-3-pentyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.00053
7-nitro-3-propyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0, 37C
0.014
7-phenylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00028 - 0.00056
7-sulfonamido-1,2,3,4-tetrahydroisoquinoline
0.0013
7-trichloromethylsulfonyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.0057
7-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.00018
7-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline
-
-
0.0000044 - 0.00026
8,9-dichloro-2,3,4,5-tetrahydro-1H-2-benzazepine
0.17
benzylamine
-
pH 8.0, 37C
0.109 - 8.298
D-norepinephrine
8
dopamine
-
competitive with phenylethanolamine
0.054
epinephrine
-
-
0.165 - 0.631
L-norepinephrine
0.0000044 - 0.00312
LY134046
0.0000013 - 0.00021
N-(4-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
0.000001 - 0.00027
N-(4-chlorophenyl)-3-(fluoromethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
0.0000014 - 0.000039
N-(4-chlorophenyl)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonamide
0.0059
norepinephrine
-
noncompetitive with phenylethanolamine
3.6
Phenylethylamine
-
competitive with phenylethanolamine
0.0000049
R-(+)-7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
-
pH 8.0
0.0124 - 0.0894
S-adenosyl-L-methionine
0.000057 - 0.321
SKF 29661
0.00000155 - 0.001375
SKF 64139
0.0021
trans-(1S,2S)-2-amino-1-tetralol
-
wild type enzyme, assay mixture consists of 25 microl of 0.5 M phosphate buffer (pH 8.0), 5 microl of [methyl-3H]S-adenosyl-L-methionine containing approximately 2.5 X 10 00000 dpm, varying amounts of phenylethanolamine and unlabeled S-adenosyl-L-methionine, 20 microl enzyme and water at 30C. The concentration of S-adenosyl-L-methionine is fixed on 5 microM.
additional information
additional information
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0019
LY134046
Homo sapiens
-
selective inhibitor, IC50: 0.0019 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000137
-
pH 8.5, 37C
0.00658
-
-
9.42
-
enzyme form E-5 from young rabbit
11.5
-
enzyme form E-5 from adult
35.9
-
enzyme form E-1 from young rabbit
51.6
-
enzyme form E-1 from adult
53.5
-
enzyme form E-4 from young rabbit
89.4
-
enzyme form E-4 from adult
175
-
enzyme form E-3 from young rabbit
188
-
enzyme form E-2 from adult
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8.2
-
phosphate buffer
7.7
-
assay at, docking to alpha-adenosyl receptor
7.9
-
Tris or borate buffer
8 - 9
-
Tris buffer
8.5
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
pheochromocytoma cell line
Manually annotated by BRENDA team
-
pheochromocytoma cell line
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
-
SDS-PAGE
30280
-
analytical ultracentrifugation, non tagged phenylethanolamine N-methyltransferase, monomer
34000
-
gel filtration
37000
-
gel filtration
38000
-
sucrose density gradient centrifugation
60550
-
analytical ultracentrifugation, non tagged phenylethanolamine N-methyltransferase, dimer
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
gel filtration reveals the presence of two species at elution volumes consistent with monomeric and dimeric human phenylethanolamine N-methyltransferase. The more prominent peak corresponds to the dimer form. The amount of dimer can be reduced either by using a more elute concentration of the protein or by the addition of 0.5 mM DTT to the running buffer. SDS-PAGE can not distinguish between the two forms. Native PAGE clearly distinguishes between the two forms of human phenylethanolamine N-methyltransferase. Crystals from the dimer fraction grow faster. Monomer and dimer human phenylethanolamine N-methyltransferase have similar kinetic constatns. The monomer-dimer equilibruim in analytical ultracentrifugation for the dimer frations of phenylethanolamine N-methyltransferase-His and C48A phenylethanolamine N-methyltransferase is 10fold lower than for the monomer fractions (Kd 35-64 microM and 305-551 microM, respectively).
monomer
-
1 * 35000, enzyme form E-3, SDS-PAGE; 1 * 40000, enzyme form E-1, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
no glycoprotein
-
enzyme contains no carbohydrate
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystallized in complex with an inhibitor and the cofactor product S-adenosyl-L-homocysteine using hanging-drop technique with PEG 6000 and lithium chloride as precipitant
-
hanging drop vapor diffusion using drops of 1 microl of protein and 1 microl of precipitant over 100 microl of precipitant [ 5-8% PEG 6K, 0.25 M LiCl, and 0.1 M sodium cacodylate (pH 5.5-6.0)]
-
hanging drop vapour diffusion method is used with 2 mircol drops on 3 M sealed over 500 mircol or 100 microl precipitant in 24-well or 96-well trays. In the absence of reducing agents crystals grow on protein concentrations of 30 to 40 mg/ml and appear in two or three days. The addition of DTT inhibits formation of crystals under the same condition. Reduced and oxidized glutathione are added to PEG/LiCl crystallisation conditions, crystals only grow in drops where the amount of oxidized glutathione is higher than reduced, the ratio of 1:20 (reduced glutathione/oxidized glutathione) gives the largest crystals.
-
hanging drop vapour diffusion on 3 M tape with 1 microl protein/ligand mixture plus 1 microl precipitant over 100 microl precipitant (0.6-0.8 M NH4H2PO4, 0.1 M citrate pH 5.3-5.8). The human phenylethanolamine N-methyltransferase S-adenosyl-L-homocysteine SKF 64139 structure is solved by difference Fourier methods and refines at 2.4 A resolution. A hydrophilic inhibitor does not bind in a distinclty differnt orientation than a hydrophobic inhibitor.
in complex with inhibitors 3-hydroxymethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline, 7-bromo-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline, 3-hydroxyethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline, 3-hydroxypropyl-7-nitro-1,2,3,4-tetrahydroisoquinoline
-
in complex with S-adenosyl-L-homocysteien and either 7-iodo-1,2,3,4-tetrahydroisoquinoline or 8,9-dichloro-2,3,4,5-tetrahydro-1H-2-benzazepine or 7-sulfonamido-1,2,3,4-tetrahydroisoquinoline
-
model is prepared on the basis of X-ray crystal structure of hPNMT in complex with S-adenosyl-L-homocysteine (AdoHcy) and the inhibitor SK&F 29661
-
purified recombinant His6-tagged wild-type and mutant K75A enzymes in complex with S-adenosyl-L-methionine or S-adenosyl-L-homocysteine, and with inhibitors (R)-4, (R)-5, (R)-6, and (R)-7, X-ray diffraction structure determination and analysis at 2.0-2.8 A resolution
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39
-
stable for at least 50 min
45
-
activity is rapidly destroyed
60
-
5 min, littel activity remains
additional information
-
presence of 2.5 mM normetanephrine has no effect on the heat denaturation, 1 mM S-adenosyl-L-methionine decreases the rate of inactivation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10C, stable for at least 1 month
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5 charge isoenzymes: E-1, E-2, E-3, E-4, E-5
-
6X-histidine tagged phenylethanolamine N-methyltransferase purified on a 10 ml column and with gel filtration. Non-tagged phenylethanolamine N-methyltransferase is purified with DEAE-Sepharose and gel filtration.
-
at least 4 active charged isoenzymes
-
enzyme form H-1 and H-2
-
His-Select HC nickel affninity column and gel filtration
recombinant C-terminally His6-tagged wild-type and mutant enzymes
-
using Ni-NTA chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C-terminally His-tagged hPNMT is expressed in Escherichia coli
-
expressed in a mouse C127 cell line
-
expressed in Escherichia coli
-
expressed in Escherichia coli as a His-tagged fusion protein
-
expressed in Escherichia coli strain BL21(DE3)-pLysS
expressed in Escherichia coli strain BL21(DE3)pLysS
-
expressed in Eschrischia coli; expression of C-terminally His6-tagged wild-type enzyme
-
expression analysis, transcriptional response of the PNMT gene to GDNF and cpt-cAMP involves distal portions of the PNMT promoter, transient expression of PNMT promoter constructs in MPC 10/9CRC1 cultures
-
expression of C-terminally His6-tagged wild-type and mutant enzymes
-
expression of wild-type enzyme and mutant enzymes in Escherichia coli
-
gene PNMT, genotyping of rs3764351 and rs876493 polymorphisms haplotypes in Japanese women, overview
-
human phenylethynolamine N-methyltransferase with a C-terminal hexahistidine tag is expressed in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
strong relationship between PNMT gene expression and tissue epinephrine levels in human pheochromocytomas
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C131S
-
mutant enzyme shows similar KM-values and maximal velocity to those of the wild-type enzyme
C139A
-
the C139A mutant separates into two forms on gel filtration, consistent with a monomer and dimer form, the equilibrium is significantly shifted in favour of the monomer. C139A mutant has similar kinetic constants as the wild type human phenylethanolamine N-methyltransferase
C139S
-
mutant enzyme shows similar KM-values and maximal velocity to those of the wild-type enzyme
C183S
-
mutant enzyme shows markedly reduced enzyme activity with less than 3% of the maximal activity of the wild-type enzyme, and ca. sixfold increased apparent KM-value for both substrates
C48A
-
the C48A mutant separates into two forms on gel filtration, consistent with a monomer and dimer form, the equilibrium is significantly shifted in favour of the monomer. C48A mutant has similar kinetic constants as the wild type human phenylethanolamine N-methyltransferase. The monomer-dimer equilibrium in analytical ultracentrifugation for the dimer fractions of phenylethanolamine N-methyltransferase-His and C48A phenylethanolamine N-methyltransferase is 10fold lower than for the monomer fractions (Kd 35-64 microM and 305-551 microM, respectively). The relative Kd values show that C48A phenylethanolamine N-methyltransferase is less likely to form dimer than phenylethanolamine N-methyltransferase-His.
C48A/C139A
-
similar kinetic constants as the wild type human phenylethanolamine N-methyltransferase
C48S
-
mutant enzyme shows similar KM-values and maximal velocity to those of the wild-type enzyme
C60S
-
mutant enzyme shows similar KM-values and maximal velocity to those of the wild-type enzyme
C91S
-
mutant enzyme shows similar KM-values and maximal velocity to those of the wild-type enzyme
D267A
higher Km and lower kcat values than wild type enzyme
E185A
-
Kcat value is reduced by 15fold. Similar Km for phenylethanolamine and slightly lower Km for AdoMet than the wild type enzyme.
E185D
-
Kcat value is reduced by 3fold. Moderately increased Km values for phenylethanolamine and AdoMet
E219A
higher Km and lower kcat values than wild type enzyme
K57A
higher Km and higher kcat values than wild type enzyme
K75A
-
crystal structure determination and comparison to the wild-type enzyme structure
V53A
higher Km and higher kcat values than wild type enzyme
Y35F
-
reduced level of binding of phenylethanolamine and AdoMet. The catalytic rate is not greatly affected by the Y35F mutation.
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
medicine
-
strong relationship between PNMT gene expression and tissue epinephrine levels in human pheochromocytomas
additional information