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2.5.1.6: methionine adenosyltransferase

This is an abbreviated version!
For detailed information about methionine adenosyltransferase, go to the full flat file.

Word Map on EC 2.5.1.6

Reaction

ATP
+
L-methionine
 +
H2O
=
phosphate
 +
diphosphate
 +
S-adenosyl-L-methionine

Synonyms

(Met) adenosyltransferase 4, adenosylmethionine synthase, adenosylmethionine synthetase, AdoMet synthase, AdoMet synthease, AdoMet synthetase, AdoMetS, ATP-methionine adenosyltransferase, ATP: L-methionine S-adenosyltransferase, EC 2.4.2.13, MAT, MAT I, MAT II, MAT IIalpha, MAT III, MAT1A, MAT2, MAT2A, MAT2beta, MAT3, MAT4, MATalpha1, MATalpha2, methionine adenosyl transferase 2A, methionine adenosyltransferase, methionine adenosyltransferase 2A, methionine adenosyltransferase 2beta, methionine adenosyltransferase 4, methionine adenosyltransferase alpha1, methionine adenosyltransferase II, methionine adenosyltransferase II-alpha, methionine adenosyltransferase IIalpha, methionine S-adenosyltransferase, methionine-activating enzyme, MetK, Mj-MAT, MJ1208, pDS16, PF1866, PfMAT, S-adenosyl-L-methionine synthetase, S-adenosyl-Lmethionine synthetase, S-adenosyl-Met synthetase 3, S-adenosylmethionine synthase, S-adenosylmethionine synthetase, S-adenosylmethionine synthetase 1, S-adenosylmethionine synthetase 2, S-adenosylmethionine synthetase 3, S-adenosylmethionine synthetase A, S-adenosylmethionine synthetase B, S-adenosylmethionine-L-synthetase, SAM synthase, SAM synthetase, SAM-s, Sam1, SAM2, SAMS, SAMS1, SAMS2, SMAT, SSO0199

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.6 methionine adenosyltransferase

Inhibitors

Inhibitors on EC 2.5.1.6 - methionine adenosyltransferase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S,4S)-amino-4,5-epoxypentanoic acid
-
1-(3-(2-ethoxyphenyl)ureidoacetyl)-4-(2-methyl-5-nitrophenyl)semicarbazide
binding to adenosyl region of the active site
1-(4-chloro-2-nitrophenyl)-3-(4-sulfamoylphenyl)-urea
binding to adenosyl region of the active site
1-aminocyclopentanecarboxylic acid
-
-
1-methyluric acid
10 mM, 43.4% inhibition
1-Methylxanthine
10 mM, 35.9% inhibition
2,6-diaminopurine
10 mM, 29.3% inhibition
2,6-dichloropurine
10 mM, 35.5% inhibition
2-amino-6-carboxyethylmercaptopurine
10 mM, 31.9% inhibition
2-amino-6-chloropurine riboside
10 mM, 17.2% inhibition
2-amino-6-chloropurine-9-acetic acid
10 mM, 23.5% inhibition
2-Aminopurine
10 mM, 11.0% inhibition
2-Hydroxypurine
10 mM, 33.8% inhibition
3,7-dimethyluric acid
10 mM, 27.9% inhibition
3-morpholinosydnoniimide
-
loss of liver MAT activity in vivo
5-amino-L-norvaline
10-25% inhibition with 5 mM; 10-25% inhibition with 5 mM; 10-25% inhibition with 5 mM
5-azacytidine
-
0.2 mM leads to significant reduction of AdoMetS protein expression
6-benzyloxypurine
10 mM, 17.7% inhibition
6-bromopurine
10 mM, 31.4% inhibition
6-Chloropurine
10 mM, 31.4% inhibition
6-Chloropurine riboside
10 mM, 17.1% inhibition
6-Cyanopurine
10 mM, 24.2% inhibition
6-dimethylallylaminopurine riboside
10 mM, 41.6% inhibition
6-Dimethylaminopurine
10 mM, 28.0% inhibition
6-Mercaptopurine
10 mM, 40.1% inhibition
6-mercaptopurine riboside
10 mM, 30.0% inhibition
6-propoxypurine
10 mM, 27.9% inhibition
7-hydroxypropyl theophylline
10 mM, 16.1% inhibition
7-Methyluric acid
10 mM, 11.4% inhibition
7-methylxanthine
10 mM, 36.3% inhibition
8-aza-2,6-diaminopurine
10 mM, 40.0% inhibition
8-Azaguanine
10 mM, 81.7% inhibition
8-chlorotheophylline
10 mM, 7.0% inhibition
Adenyl-5'-ylimidodiphosphate
-
competitive with ATP
ADP
35-50% inhibition with 5 mM; 35-50% inhibition with 5 mM; 35-50% inhibition with 5 mM
alpha,beta-methylene-adenosine tetraphosphate
-
-
alpha,beta-methylene-ATP
-
-
alpha-methyl-DL-methionine
10 mM, 18.8% inhibition
AMP
causes complete inactivation of the enzyme
Azathioprine
10 mM, 75.5% inhibition
Ba2+
70.70% residual activity at 5 mM
bacterial lipopolysaccharide
-
beta,gamma-methylene-ATP
-
-
Br-
93.33% residual activity at 5 mM
carbon tetrachloride
-
depletion of glutathione levels reduces MAT I/III activities in vivo
CH3COO-
92.25% residual activity at 5 mM
Cl-
85.27% residual activity at 5 mM
Co2+
-
about 45% residual activity at 10 mM
cycloleucine
diimidotriphosphate
mechanism
Dimethylsulfoxide
diphosphate
DL-2-Amino-trans-4-hexenoic acid
-
-
ethanol
25 mM ethanol substantially decreases the enzymatic activity of MAT II
Ethionine
32-38% inhibition with 5 mM; 32-38% inhibition with 5 mM; 32-38% inhibition with 5 mM
F-
88.84% residual activity at 5 mM
fluorinated N,N-dialkylaminostilbene-5
-
i.e. FIDAS
-
Fumarylacetoacetate
-
reduces MAT I/III activity
glycerol
-
inhibits kidney isoenzyme gamma
GSH
causes complete inactivation of the enzyme
hydrogen peroxide
I-
87.91% residual activity at 5 mM
L-2-Amino-4-hexynoic acid
-
-
L-2-Amino-4-methoxy-cis-but-3-enoic acid
L-2-Amino-4-methylthio-cis-but-3-enoic acid
-
-
L-buthionine-(S,R)-sulfoximine
L-ethioninamide
10 mM, 23.9% inhibition
L-ethionine
L-methionine
L-methionine methyl ester
10 mM, 17.7% inhibition
L-methionine sulfone
10 mM, 9.2% inhibition
L-methionine sulfoxide
10 mM, 4.0% inhibition
L-methionine sulfoximine
10 mM, 12.6% inhibition
L-Penicillamine
10 mM, 15.0% inhibition
Li+
81.40% residual activity at 5 mM
methanol
2.4% methanol depresses methionine adenosyltransferase specific activity, this effect is not observed with 0.8% methanol
methylthio propionaldehyde
10 mM, 18.4% inhibition
methylthioadenosine
Mg2+
-
inhibitory above 8.5 mM
N-ethylmaleimide
time-dependent inactivation of both MAT activities
Ni2+
-
about 1% residual activity at 10 mM
nitric oxide
nitrosoglutathione
-
reversibly inhibits the isozyme MAT1 via NO binding to Cys114, no inhibition of isozymes MAT2 and MAT3, molecular mechanism for S-nitrosylation of the enzyme
NO
the enzyme is inhibited upon S-nitrosylation. S-Nitrosylation of the enzyme is mediated via several cysteine residues, including Cys52, Cys113 and Cys187. Nitrosylation is a reversible posttranslational modification upon nitrosative stress
O-methylguanine
10 mM, 60.3% inhibition
p-chloromercuribenzoate
phosphate
putrescine
15-25% inhibition with 5 mM; 15-25% inhibition with 5 mM; 15-25% inhibition with 5 mM
S-adenosyl-L-ethionine
-
-
S-adenosyl-L-homocysteine
S-adenosyl-L-methionine
S-adenosylmethionine
S-carbamylcysteine
-
competitive with methionine
S-nitrosoglutathione
S-nitrosoglutathione monoethyl ester
-
inactivates
S-nitrosylated glutathione
-
rapid and dose-dependent loss of enzymatic activity of MAT I/III
S-Trifluoromethyl-L-homocysteine
-
-
seleno-L-methionine
-
-
SIN-1
-
rapid and dose-dependent loss of enzymatic activity of MAT I/III
Sodium diphosphate
-
-
spermidine
15-34% inhibition with 5 mM; 15-34% inhibition with 5 mM; 15-34% inhibition with 5 mM
spermine
30-40% inhibition with 5 mM; 30-40% inhibition with 5 mM; 30-40% inhibition with 5 mM
Tetrapolyphosphate
tripolyphosphate
uric acid
10 mM, 45.6% inhibition
xanthine
10 mM, 35.4% inhibition
additional information
-