Information on EC 2.3.1.5 - arylamine N-acetyltransferase and Organism(s) Homo sapiens and UniProt Accession P11245

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This record set is specific for:
Homo sapiens
UNIPROT: P11245


The expected taxonomic range for this enzyme is: Bacteria, Eukaryota


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
2.3.1.5
-
RECOMMENDED NAME
GeneOntology No.
arylamine N-acetyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + an arylamine = CoA + an N-acetylarylamine
show the reaction diagram
acetyl-CoA + an arylamine = CoA + an N-acetylarylamine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Caffeine metabolism
-
-
Nitrotoluene degradation
-
-
Drug metabolism - other enzymes
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
Microbial metabolism in diverse environments
-
-
SYSTEMATIC NAME
IUBMB Comments
acetyl-CoA:arylamine N-acetyltransferase
Wide specificity for aromatic amines, including serotonin; also catalyses acetyl-transfer between arylamines without CoA.
CAS REGISTRY NUMBER
COMMENTARY hide
9027-33-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-nitrophenyl acetate + 4-amino-3-methylbenzoic acid
4-nitrophenol + N-acetyl-4-amino-3-methylbenzoic acid
show the reaction diagram
4-nitrophenyl acetate + 4-aminobenzoic acid
4-nitrophenol + N-acetyl-4-aminobenzoic acid
show the reaction diagram
4-nitrophenyl acetate + 4-aminobiphenyl
4-nitrophenol + N-acetyl-4-aminobiphenyl
show the reaction diagram
4-nitrophenyl acetate + 5-aminosalicylic acid
4-nitrophenol + 5-acetylaminosalicylic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2-aminofluorene
CoA + 2-acetylaminofluorene
show the reaction diagram
acetyl-CoA + 2-aminofluorene
CoA + N-acetyl-2-aminofluorene
show the reaction diagram
-
-
-
?
acetyl-CoA + 4-aminobenzoate
CoA + N-acetyl-4-aminobenzoate
show the reaction diagram
-
6% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-aminosalicylic acid
CoA + N-acetyl-4-aminosalicylic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + 4-aminoveratrole
CoA + N-acetyl-4-aminoveratrole
show the reaction diagram
-
57% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-bromoaniline
CoA + N-acetyl-4-bromoaniline
show the reaction diagram
-
72% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-chloroaniline
CoA + N-acetyl-4-chloroaniline
show the reaction diagram
-
71% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-dimethylaminobenzaldehyde
CoA + 5-acetyl-4-dimethylaminobenzaldehyde
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-hexyloxyaniline
CoA + N-acetyl-4-hexyloxyaniline
show the reaction diagram
-
51% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-iodoaniline
CoA + N-acetyl-4-iodoaniline
show the reaction diagram
-
65% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-methoxyaniline
CoA + N-acetyl-4-methoxyaniline
show the reaction diagram
-
9% activity compared to hydralazine
-
-
?
acetyl-CoA + 4-phenoxyaniline
CoA + N-acetyl-4-phenoxyaniline
show the reaction diagram
-
62% activity compared to hydralazine
-
-
?
acetyl-CoA + 5-aminosalicylate
CoA + N-acetyl-5-aminosalicylate
show the reaction diagram
-
64% activity compared to hydralazine
-
-
?
acetyl-CoA + 5-aminosalicylic acid
CoA + 5-acetylaminosalicylic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 5-aminosalicylic acid
CoA + N-acetyl-5-aminosalicylic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + an arylamine
CoA + an N-acetylarylamine
show the reaction diagram
acetyl-CoA + hydralazine
CoA + N-acetylhydralazine
show the reaction diagram
-
100% activity
-
-
?
acetyl-CoA + isoniazid
CoA + N-acetylisoniazid
show the reaction diagram
-
62% activity compared to hydralazine
-
-
?
acetyl-CoA + N-(4-aminobenzoyl)-L-glutamate
CoA + N-(4-acetylaminobenzoyl)-L-glutamate
show the reaction diagram
-
3% activity compared to hydralazine
-
-
?
acetyl-CoA + p-aminobenzoic acid
CoA + N-acetyl-p-aminobenzoic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + procainamide
CoA + N-acetyl-2-procainamide
show the reaction diagram
-
-
-
?
acetyl-CoA + sulfamethazine
?
show the reaction diagram
-
-
-
?
acetyl-CoA + sulfamethazine
CoA + N-acetyl-sulfamethazine
show the reaction diagram
acetyl-CoA + sulfamethazine
CoA + N-acetylsulfamethazine
show the reaction diagram
-
46% activity compared to hydralazine
-
-
?
3'-dephospho-acetyl-CoA + 4-aminobenzoate
3'-dephospho-CoA + N-acetyl-4-aminobenzoate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + 4-amino-3-methylbenzoic acid
4-nitrophenol + N-acetyl-4-amino-3-methylbenzoic acid
show the reaction diagram
4-nitrophenyl acetate + 4-aminobenzoate
4-nitrophenol + N-acetyl-4-aminobenzoate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + 4-aminobenzoic acid
4-nitrophenol + N-acetyl-4-aminobenzoate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + 4-aminobenzoic acid
4-nitrophenol + N-acetyl-4-aminobenzoic acid
show the reaction diagram
4-nitrophenyl acetate + 4-aminobiphenyl
4-nitrophenol + N-acetyl-4-aminobiphenyl
show the reaction diagram
4-nitrophenyl acetate + 5-aminosalicylic acid
4-nitrophenol + 5-acetylaminosalicylic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + (1-methyl-5-piperazin-1-yl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)-(5-methyl-pyridin-2-yl)-amine
CoA + ?
show the reaction diagram
-
i.e. UK-469,413. Acetylation by isozyme NAT2 in liver cytosol to N-acetylpiperazine metabolite
-
-
?
acetyl-CoA + 2,3-dimethylaniline
CoA + N-acetyl-2,3-dimethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2,4-dimethylaniline
CoA + N-acetyl-2,4-dimethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2,5-dimethylaniline
CoA + N-acetyl-2,5-dimethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2-(4-aminobenzamido)pyridine
CoA + 2-(4-acetylamidobenzamido)pyridine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2-aminobenzoic acid
CoA + N-acetyl-2-aminobenzoic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2-aminofluorene
CoA + 2-acetylaminofluorene
show the reaction diagram
acetyl-CoA + 2-aminofluorene
CoA + N-acetyl-2-aminofluorene
show the reaction diagram
acetyl-CoA + 2-ethylaniline
CoA + N-acetyl-2-ethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 2-methylaniline
CoA + N-acetyl-2-methylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 3,4-dimethylaniline
CoA + N-acetyl-3,4-dimethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 3,5-dimethylaniline
CoA + N-acetyl-3,5-dimethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 3-ethylaniline
CoA + N-acetyl-3-ethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-aminobenzoate
CoA + N-acetyl-4-aminobenzoate
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-aminobenzoic acid
CoA + 4-(acetylamino)benzoic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-aminobenzoic acid
CoA + 4-acetylaminobenzoic acid
show the reaction diagram
acetyl-CoA + 4-aminobenzoic acid
CoA + N-acetyl-4-aminobenzoic acid
show the reaction diagram
acetyl-CoA + 4-aminobiphenyl
CoA + N-acetyl-4-aminobiphenyl
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-aminosalicylate
CoA + N-acetyl-4-aminosalicylate
show the reaction diagram
-
substrate for isoform NAT1
-
-
?
acetyl-CoA + 4-aminosalicylic acid
CoA + 4-acetylamino-2-hydroxybenzoate
show the reaction diagram
acetyl-CoA + 4-aminosalicylic acid
CoA + N-acetyl-4-aminosalicylic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + 4-dimethylaminobenzaldehyde
CoA + 5-acetyl-4-dimethylaminobenzaldehyde
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-ethylaniline
CoA + N-acetyl-4-ethylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 4-methylaniline
CoA + N-acetyl-4-methylaniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 5-aminosalicylic acid
CoA + 5-acetylamino-2-hydroxybenzoate
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 5-aminosalicylic acid
CoA + 5-acetylaminosalicylic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + 5-aminosalicylic acid
CoA + N-acetyl-5-aminosalicylic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + 8-aminoisoindolo (1,2-b)quinazolin-12(10H)-one
?
show the reaction diagram
-
batricylin, an antitumor agent, is shown to be a substrate for NAT2
-
-
-
acetyl-CoA + an arylamine
CoA + a N-acetylarylamine
show the reaction diagram
acetyl-CoA + an arylamine
CoA + an N-acetylarylamine
show the reaction diagram
acetyl-CoA + aniline
CoA + N-acetyl-aniline
show the reaction diagram
-
-
-
-
?
acetyl-CoA + diaminodiphenylsulfone
monoacetyldiaminodiphenylsulfone + CoA
show the reaction diagram
-
i.e. dapsone, predominantly acetylated by NAT2
-
-
?
acetyl-CoA + hydralazine
CoA + N-acetylhydralazine
show the reaction diagram
-
substrate for isoform NAT2
-
-
?
acetyl-CoA + isoniazid
?
show the reaction diagram
acetyl-CoA + isoniazid
CoA + N-acetyl-isoniazid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + isoniazide
CoA + acetylniazide
show the reaction diagram
-
-
-
-
?
acetyl-CoA + N-(4-aminobenzoyl)-L-glutamate
CoA + N-(4-acetylaminobenzoyl)-L-glutamate
show the reaction diagram
acetyl-CoA + p-aminobenzoic acid
CoA + N-acetyl-4-aminobenzoic acid
show the reaction diagram
acetyl-CoA + p-aminobenzoic acid
CoA + N-acetyl-aminobenzoic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + p-aminobenzoic acid
CoA + N-acetyl-p-aminobenzoic acid
show the reaction diagram
-
-
-
?
acetyl-CoA + p-aminobenzoylglutamate
CoA + N-[(4-acetylamino)]benzoyl-L-glutamate
show the reaction diagram
-
-
-
-
?
acetyl-CoA + p-aminosalicylic acid
CoA + N-acetyl-4-aminosalicylic acid
show the reaction diagram
-
-
-
-
?
acetyl-CoA + peptide
CoA + Nalpha-acetylpeptide
show the reaction diagram
-
-
-
-
?
acetyl-CoA + procainamide
CoA + N-acetyl-2-procainamide
show the reaction diagram
-
-
-
?
acetyl-CoA + procainamide
CoA + N-acetylprocainamide
show the reaction diagram
acetyl-CoA + sulfadiazine
CoA + ?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sulfadiazine
CoA + N-acetylsulfadiazine
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sulfamerazine
CoA + ?
show the reaction diagram
-
-
-
-
?
acetyl-CoA + sulfamethazine
?
show the reaction diagram
-
-
-
?
acetyl-CoA + sulfamethazine
CoA + N-4-acetylsulfamethazine
show the reaction diagram
acetyl-CoA + sulfamethazine
CoA + N-acetyl-sulfamethazine
show the reaction diagram
p-nitrophenylacetate + p-aminosalicylic acid
?
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
4-nitrophenyl acetate + 4-amino-3-methylbenzoic acid
4-nitrophenol + N-acetyl-4-amino-3-methylbenzoic acid
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + 4-aminobenzoic acid
4-nitrophenol + N-acetyl-4-aminobenzoic acid
show the reaction diagram
-
a sunscreen additive
-
-
?
4-nitrophenyl acetate + 4-aminobiphenyl
4-nitrophenol + N-acetyl-4-aminobiphenyl
show the reaction diagram
-
a tobacco smoke carcinogen
-
-
?
acetyl-CoA + 2-aminofluorene
CoA + 2-acetylaminofluorene
show the reaction diagram
-
-
-
-
?
acetyl-CoA + an arylamine
CoA + an N-acetylarylamine
show the reaction diagram
4-nitrophenyl acetate + 4-amino-3-methylbenzoic acid
4-nitrophenol + N-acetyl-4-amino-3-methylbenzoic acid
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + 4-aminobenzoic acid
4-nitrophenol + N-acetyl-4-aminobenzoic acid
show the reaction diagram
-
a sunscreen additive
-
-
?
4-nitrophenyl acetate + 4-aminobiphenyl
4-nitrophenol + N-acetyl-4-aminobiphenyl
show the reaction diagram
-
a tobacco smoke carcinogen
-
-
?
acetyl-CoA + 2-aminofluorene
CoA + 2-acetylaminofluorene
show the reaction diagram
-
-
-
-
?
acetyl-CoA + an arylamine
CoA + a N-acetylarylamine
show the reaction diagram
acetyl-CoA + an arylamine
CoA + an N-acetylarylamine
show the reaction diagram
acetyl-CoA + peptide
CoA + Nalpha-acetylpeptide
show the reaction diagram
-
-
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
folate
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
curcumin
-
non-competitive
esculetin
-
-
genistein
-
-
kaemferol
-
non-competitive
quercetin
-
non-competitive
scopoletin
-
-
silymarin
-
-
taxifolin
-
-
(-)-epigallocatechin-3-O-gallate
-
EGCG, non-competitive
(5Z)-3-amino-5-(3-hydroxy-2,4-diiodobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
(5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
(5Z)-5-(2-methylbenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
(5Z)-5-(3,4-dichlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
(5Z)-5-(3-hydroxy-2,4-diiodobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
(5Z)-5-(3-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
(5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
-
inhibition of both recombinant enzyme and native enzyme in ZR-75 cell lysate, competitive
1-butoxy-2-methylbenzene
-
-
2-bromoacetanilide
-
irreversible inhibitor
2-butoxyphenol
-
-
2-nitrosofluorene
-
; potent inactivator, incubation with 2-nitrosofluorene causes 91% inactivation. In the presence of a 500fold excess of glutathione (0.5 mM), inhibition is reduced to 28%
2-nitrosotoluene
-
; less potent inactivator of NAT1, NAT1 with 2-nitrosotoluene causes 46% inhibition of the enzyme, whereas the presence of AcCoA lowers the extent of inhibition to 5%
4-nitrosobenzene
-
less potent inactivator of NAT1, NAT1 with nitrosobenzene causes 59% inhibition of the enzyme, whereas the presence of AcCoA lowers the extent of inhibition to 13%
4-nitrosobiphenyl
-
; potent inactivator, incubation with 4-nitrosobiphenyl causes 71% inactivation. In the presence of a 500fold excess of glutathione (0.5 mM), inhibition is reduced to 35%
5-methoxypsoralen
-
i.e. 5-MOP, activates the enzyme at 50 mM in Colo 205 cells, inhibitory at lower dosage of 0.05-0.5 mM, concentrations of 5-25 mM have no effect in Colo 205 cells
acetoaminophen
-
-
Benzyl isothiocyanate
-
-
beta-methylesculetin
-
inhibits NAT2 but not NAT1
caffeic acid
cisplatin
-
; exposure of MCF-7 breast cancer cells to cisplatin at clinically relevant concentrations (below 0.4 nM) causes significant dose-dependent inhibition of the endogenous NAT1 enzyme. The incubation of NAT1 with various concentrations of cisplatin results in the dose-dependent modification of cysteine residues, as indicated by the disappearance of fluorescein-conjugated iodoacetamide labeling
curcumin
-
inhibits NAT2 but not NAT1
cytokine
-
mixture of proinflammatory cytokines, interferon-gamma, interleukin-1beta, tumor necrosis factor-alpha
-
dihydrofolic acid
-
-
ellagic acid
-
-
esculetin
-
-
ferulic acid
folic acid
-
competitive
gallic acid
genistein
-
-
glycyrrhizic acid
-
-
H2O2
-
NAT1 is reversibly inactivated by physiological aoncentrations of hydrogen peroxide. Inactivation of NAT1 is fully reversed by physiological concentrations of GSH
hydrogen peroxide
Ibuprofen
-
-
kaemferol
-
non-competitive
kaempferol
-
inhibits NAT1 and NAT2
Ketoprofen
-
competitive inhibitor of NAT enzymes
luteolin
-
-
methotrexate
-
competitive
N-(3-((2''-methoxyethyl)amino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(2''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenoxy)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenylamino)-5-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenylamino)-6-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenylamino)-7-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3'',5''-dimethylphenylamino)-8-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide
-
-
-
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
-
-
-
N-(3-(4''-bromophenoxy)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(4''-bromophenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(4''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(4''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(benzylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(cyclopentylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(3-(furan-2''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
-
-
-
N-(3-(furan-3''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
-
-
-
N-(3-(furan-3''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
-
-
-
N-(3-phenoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
-
-
-
N-(3-phenylamino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
-
-
-
N-(5-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(6-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(7-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(8-amino-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(8-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-(8-nitro-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
-
-
-
N-ethylmaleimide
-
-
N-Hydroxy-2-acetylaminofluorene
-
mechanism-based inactivator, kinetics
N-[3-(3,5-dimethylanilino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]-N-methylbenzenesulfonamide
-
-
N-[3-(3,5-dimethylanilino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzenesulfonamide
nitrosobenzene
-
-
paclitaxel
-
inhibits NAT1 and NAT2
peroxinitrite
-
rapid and irreversible inactivation
peroxynitrite
phenethyl isothiocyanate
-
-
piperidinol
-
strong inhibition
proinflammatory cytokine
-
treatment of cholangiocarcinoma KKU-100 cells with cytokines (interferon-gamma, interleukin-1beta and tumor necrosis factor-alpha) suppresses NAT1 activity, reducing the Vmax without affecting the Km
-
quercetin
rhodanine
-
-
S-nitroso-glutathione
-
treatment of cholangiocarcinoma KKU-100 cells S-nitroso-glutathione results in reduced NAT1 activity as early as 2 h, and the suppression persists for 48 h
S-nitroso-N-acetyl-DL-penicillamine
-
reversible inactivation due to direct atteck of the highly reactive cysteine residue in the enzyme active site on the sulfur of S-nitrosothiols to form a mixed disulfide between these NO-derived oxidants and NAT1
S-nitrosoglutathione
-
-
SiO2
-
-
tamoxifen
-
-
taxifolin
-
-
TiO2
-
-
vitamin C
-
-
ZnO
-
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5-methoxypsoralen
-
i.e. 5-MOP, activates the enzyme at 50 mM in Colo 205 cells, inhibitory at lower dosage of 0.05-0.5 mM in Colo 205 cells and at 0.5-0.25 mM in SC-M1 cells, concentrations of 5-25 mM have no effect in Colo 205 cells
glycyrrhizic acid
-
slightly activates isozyme NAT1
R1881
the androgen R1881 induces NAT1 activity in androgen receptor-positive prostate cancer cells
thermo-responsive diblock copolymer nanoparticle
-
-
-
additional information
the androgen R1881 induces the enzyme about 4.5fold in androgen receptor AR-positive prostate cell lines 22Rv1 and LNCaP, but not in the AR-negative PC-3, HK-293, or HeLa cells, androgen up-regulation of NAT1 is prevented by the AR antagonist flutamide, the effect of R1881 may not be by direct transcriptional activation of NAT1, overview
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.6
2-toluidine
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
11
4-amino-3-methylbenzoic acid
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
166
4-Aminobenzoic acid
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
0.184
5-aminosalicylic acid
isoform NAT 2, pH 7.4, 37C
1.11 - 5.53
2,3-dimethylaniline
2.06 - 5.03
2,4-dimethylaniline
3.12 - 6.73
2,5-dimethylaniline
0.109 - 0.857
2-Aminofluorene
2.11
2-ethylaniline
-
-
2.32 - 7.18
2-methylaniline
1.2
2-toluidine
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
0.352 - 0.688
3,4-dimethylaniline
0.28 - 0.742
3,5-dimethylaniline
0.576 - 1.32
3-ethylaniline
0.17
4-amino-3-methylbenzoic acid
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
0.106
4-Aminobenzoate
-
at pH 7.4 and 37C
0.049
4-Aminobenzoic acid
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
0.191 - 0.486
4-aminobiphenyl
0.205 - 3.27
4-ethylaniline
0.483 - 118
4-methylaniline
0.0067
5-aminosalicylic acid
isoform NAT 1, pH 7.4, 37C
0.0543 - 0.438
acetyl-CoA
2.49 - 112
aniline
0.366 - 0.374
isoniazid
0.38 - 0.58
isoniazide
-
-
0.0028 - 152
p-Aminobenzoic acid
0.059 - 5.39
p-Aminosalicylic acid
45
procainamide
-
isozyme NAT1
3.1
Sulfadiazine
-
-
0.02 - 5.39
sulfamethazine
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
72
2-toluidine
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
16.6
4-amino-3-methylbenzoic acid
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
21
4-Aminobenzoic acid
-
pH 7.0, 23C, isozyme NAT2, with 4-nitrophenyl acetate
27 - 256
2,3-dimethylaniline
67 - 661
2,4-dimethylaniline
5.7 - 313
2,5-dimethylaniline
449 - 759
2-Aminofluorene
61
2-ethylaniline
-
-
12 - 111
2-methylaniline
6.3
2-toluidine
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
461 - 800
3,4-dimethylaniline
308 - 1220
3,5-dimethylaniline
310 - 1960
3-ethylaniline
1.3
4-amino-3-methylbenzoic acid
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
127
4-Aminobenzoic acid
-
pH 7.0, 23C, isozyme NAT1, with 4-nitrophenyl acetate
243 - 256
4-aminobiphenyl
430 - 700
4-ethylaniline
303 - 1600
4-methylaniline
281 - 711
aniline
38 - 298
p-Aminobenzoic acid
27 - 591
p-Aminosalicylic acid
387
sulfamethazine
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
quercetin
-
isozyme NAT2
0.54
4-nitrosobenzene
-
-
0.00067
4-nitrosobiphenyl
-
; recombinant NAT1
0.54
nitrosobenzene
-
recombinant NAT1
0.0486
quercetin
-
isozyme NAT1
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0011
(5Z)-3-amino-5-(3-hydroxy-2,4-diiodobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0011
(5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0039
(5Z)-5-(2-methylbenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0034
(5Z)-5-(3,4-dichlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0018
(5Z)-5-(3-hydroxy-2,4-diiodobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0006
(5Z)-5-(3-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.0047
(5Z)-5-(4-chlorobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens;
-
pH 8.0, 25C
0.00004
2-nitrosofluorene
Homo sapiens;
-
; HeLa cell NAT1
0.091
2-nitrosotoluene
Homo sapiens;
-
; HeLa cell NAT1
0.237
4-nitrosobenzene
Homo sapiens;
-
-
0.00006
4-nitrosobiphenyl
Homo sapiens;
-
; HeLa cell NAT1
0.007
Benzyl isothiocyanate
Homo sapiens;
-
at pH 7.5 and 37C
0.1
cisplatin
Homo sapiens;
-
in MCF-7 breast cancer cells; in MCF7-cells, similar results with MDA-MB-231 cells
0.03
N-(3-((2''-methoxyethyl)amino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.008
N-(3-(2''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0121
N-(3-(3'',5''-dimethylphenoxy)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0041
N-(3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0066
N-(3-(3'',5''-dimethylphenylamino)-5-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.03
N-(3-(3'',5''-dimethylphenylamino)-6-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide, N-(3-(3'',5''-dimethylphenylamino)-8-nitro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0145
N-(3-(3''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.01 - 0.019
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzamide
-
0.0084
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0221
N-(3-(3''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0019
N-(3-(4''-bromophenoxy)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0009
N-(3-(4''-bromophenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0121
N-(3-(4''-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0103
N-(3-(4''-formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.03
N-(3-(benzylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide, N-(3-(cyclopentylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0096
N-(3-(furan-2''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.01
N-(3-(furan-3''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0193
N-(3-(furan-3''-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)phenylacetamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0028
N-(3-phenoxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0017
N-(3-phenylamino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0042
N-(5-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0026
N-(7-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.00012
N-(8-amino-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.00054
N-(8-amino-3-(3'',5''-dimethylphenylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.03
N-(8-nitro-1,4-dioxo-3-(phenylamino)-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
-
0.0058
N-[3-(3,5-dimethylanilino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]-N-methylbenzenesulfonamide
Homo sapiens;
-
pH and temperature not specified in the publication
0.0053
N-[3-(3,5-dimethylanilino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]benzenesulfonamide
Homo sapiens;
-
isoform NAT1, pH and temperature not specified in the publication
0.237
nitrosobenzene
Homo sapiens;
-
HeLa cell NAT1
0.015
phenethyl isothiocyanate
Homo sapiens;
-
at pH 7.5 and 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000000002
isoform NAT 2, p-aminobenzoic acid, pH 7.4, 37C
0.00000006
isoform NAT 2, procainamide, pH 7.4, 37C
0.000000075
isoform NAT 2, 4-aminosalicylic acid, pH 7.4, 37C
0.00000099
isoform NAT 2, 2-aminofluorene, pH 7.4, 37C
0.00000189
isoform NAT 2, 5-aminosalicylic acid, pH 7.4, 37C
0.00000241
isoform NAT 2, sulfamethazine, pH 7.4, 37C
0.00000568
isoform NAT 1, procainamide, pH 7.4, 37C
0.0000083
isoform NAT 1, sulfamethazine, pH 7.4, 37C
0.0001
-
breast cancer cell line Cal51c, estrogen receptor (ER)-negative; CAL-51 cell
0.0002
-
breast cancer cell line MDA-MB-231, estrogen receptor (ER)-negative; MDA-MB-231 cell
0.0005
-
mutant GGSG; mutant HHEH
0.00052
isoform NAT 1, 2-aminofluorene, pH 7.4, 37C
0.00058
isoform NAT 1, p-aminobenzoic acid, pH 7.4, 37C
0.0006
-
mutant GGSG; mutant HHEH
0.0007
-
breast cancer cell line MDA-MB-436, estrogen receptor (ER)-negative; MDA-MB-436 cell
0.001
-
breast cancer cell line MCF-7, estrogen receptor (ER)-positive
0.00109
isoform NAT 1, 4-aminosalicylic acid, pH 7.4, 37C
0.00117
isoform NAT 1, 5-aminosalicylic acid, pH 7.4, 37C
0.0013
-
mutant GRSG
0.0014
-
mutant GRSG
0.00161
-
HeLa cell + N-acetyl-L-cysteine + 4-nitrosobiphenyl
0.00172
-
HeLa cell + 4-nitrosobiphenyl
0.0018
-
MCF-7 cell
0.0021
-
breast cancer cell line MDA-MB-453, estrogen receptor (ER)-negative; MDA-MB-453 cell
0.00408
-
in HeLa cells, substrate: p-aminosalicylic acid
0.0044
-
in HeLa cells, substrate: p-aminobenzoic acid
0.00454
-
HeLa cell + N-acetyl-L-cysteine
0.00466
-
HeLa cell
0.005
-
breast cancer cell line T47D, estrogen receptor (ER)-positive
0.0054
-
T-47D cell
0.0055
-
mutant GG
0.006
-
mutant GG
0.0061
-
-
0.0064
-
-
0.008
-
enzymatic activity found in peripheral blood mononuclear cell of investigated donors: 8-23.5 nmol/mg/min
0.01
HEK-293 cell, treated with R1881; PC-3 cell
0.0104
effect of androgen receptor expression in PC-3 cells, control, plus R1881
0.0105
-
enzymatic activity found in HepG2 cells
0.0109
effect of androgen receptor expression in PC-3 cells, plus pCMV-AR3.1, plus R1881
0.011
HEK-293 cell; PC-3 cell, treated with R1881
0.0113
effect of androgen receptor expression in PC-3 cells, control
0.0115
effect of androgen receptor expression in PC-3 cells, plus pCMV-AR3.1
0.014
HeLa cell
0.015
HeLa cell, treated with R1881
0.0234
-
enzymatic activity found in monocyte-derived dendritic cells of investigated donors: 23.4-26.6 nmol/mg/min
0.038
22Rv1 cell, plus R1881, plus flutamide
0.04
22Rv1 cell, 24h; 22Rv1 cell, 48h; 22Rv1 cell, plus bicalutamide, 24h; 22Rv1 cell, plus bicalutamide, 48h; 22Rv1 cell, plus R1881, plus bicalutamide; 22Rv1 cell, plus R1881, plus bicalutamide, 24h
0.042
22Rv1 cell, plus DMSO
0.045
LNCaP cell
0.046
22Rv1 cells and LNCAP cells (both androgene-positive lines) show a high basal level of NAT1 activity between 46-51 nmol/min/mg protein
0.05
22Rv1 cell
0.054
-
cytokine mixture, 2.5 microM p-aminobenzoic acid
0.07
22Rv1 cell, plus R1881; LNCaP cell, treated with R1881
0.08
22Rv1 cell, plus R1881, 24h
0.097
-
cytokine mixture, 7.5 microM p-aminobenzoic acid
0.108
-
control, 2.5 microM p-aminobenzoic acid
0.124
-
cytokine mixture, 40 microM p-aminobenzoic acid
0.13
22Rv1 cell, treated with R1881
0.14
22Rv1 prostate cells upon treatment with 100 nmol of synthetic androgen R1881 for 24h
0.146
-
control, 7.5 microM p-aminobenzoic acid
0.2
-
control, 40 microM p-aminobenzoic acid
0.202
-
breast cancer cell line ZR-75-1, estrogen receptor (ER)-positive
0.2022
-
ZR-75-1 cell
0.237
-
recombinant NAT1, substrate: p-aminobenzoic acid
0.337
-
recombinant NAT1, substrate: p-aminosalicylic acid
0.55
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
7.5
-
assay at
7
-
assay at
additional information
-
pI: 4.8
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23
-
assay at
23
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 33
-
mutant GG
30 - 50
-
control
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
healthy and neoplastic tissue
Manually annotated by BRENDA team
-
patients with ductal carcinoma
Manually annotated by BRENDA team
-
isozyme NAT2 mainly
Manually annotated by BRENDA team
-
type II alveolar cell, presence of isoform Nat1. Exposure of cells to pathophysiologically relevant amounts of oxidants such as H2O2 or peroxyntrite, impairs the cellular biotransformation of aromatic amines
Manually annotated by BRENDA team
-
healthy and neoplastic tissue
Manually annotated by BRENDA team
-
presence of isoform Nat1. Exposure of cells to pathophysiologically relevant amounts of oxidants such as H2O2 or peroxyntrite, impairs the cellular biotransformation of aromatic amines
Manually annotated by BRENDA team
-
; breast cancer cell line, estrogen receptor (ER)-negative, expression below detection limits in Western blot analysis
Manually annotated by BRENDA team
-
presence of isoform Nat1. Exposure of cells to pathophysiologically relevant amounts of oxidants such as H2O2 or peroxyntrite, impairs the cellular biotransformation of aromatic amines
Manually annotated by BRENDA team
-
isoform NAT2
Manually annotated by BRENDA team
-
high activity of isozyme NAT1
Manually annotated by BRENDA team
-
a cholangiocarcinoma cell line, isozyme NAT1
Manually annotated by BRENDA team
-
; breast cancer cell line, estrogen receptor (ER)-negative, expression below detection limits in Western blot analysis
Manually annotated by BRENDA team
-
; breast cancer cell line, estrogen receptor (ER)-negative, expression below detection limits in Western blot analysis
Manually annotated by BRENDA team
-
NAT-1 mRNA expression is found in 9 of 10 donors; NAT-2 mRNA expression weaker thn NAT-1 mRNA expression
Manually annotated by BRENDA team
-
; NAT-1 mRNA expression is found in 5 of 7 examined individuals
Manually annotated by BRENDA team
-
expressed in placenta during the first trimester of embryonic development
Manually annotated by BRENDA team
-
androgen-dependent expression of NAT1 is demonstrated
Manually annotated by BRENDA team
NAT1 is strongly localized to androgen-positive epithelium in human prostate
Manually annotated by BRENDA team
-
both NAT2 mRNA and enzyme are readily detected in fetal, newborn, and adult muscles. High expression in fetal muscle. Despite the presence of its mRNA, NAT2 enzyme level is below the limit of detection
Manually annotated by BRENDA team
-
; breast cancer cell line, estrogen receptor (ER)-positive, expression below detection limits in Western blot analysis
Manually annotated by BRENDA team
-
high activity of isozyme NAT1
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
isozyme NAT2
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
UNIPROT
ORGANISM
P11245
Homo sapiens;
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26500
-
gel filtration
31000
-
1 * 31000, SDS-PAGE
33840
-
mass spectrometry
34000
-
x * 34000, SDS-PAGE
35000
-
HeLa cell NAT1, determined by SDS-PAGE and Western blot analysis
37000
-
recombinant NAT1, determined by SDS-PAGE and Western blot analysis
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 31000, SDS-PAGE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with coenzyme A
high resolution crystal structures of both human NATs, including NAT1 in complex with the irreversible inhibitor 2-bromoacetanilide, a site-directed NAT1 mutant, NAT1-F125S, and a NAT2-CoA complex are presented. By comparing the structures with known prokaryotic structures, evidences are provided for novel structural features of human NATs that are absent in bacterial enzymes, including an insertion that produces a significant difference in the structure of the carboxyl terminus of the eukaryotic enzymes; high resolution crystal structures of both human NATs, including NAT1 in complex with the irreversible inhibitor 2-bromoacetanilide, a site-directed NAT1 mutant, NAT1-F125S, and a NAT2-CoA complex are presented. By comparing the structures with known prokaryotic structures, evidences are provided for novel structural features of human NATs that are absent in bacterial enzymes, including an insertion that produces a significant difference in the structure of the carboxyl terminus of the eukaryotic enzymes. A complete picture of the distinct substrate selectivity of human NAT1 and NAT2, as well as key features of the naturally occurring variants of NAT1 and NAT2 is provided
-
in complex with 2-bromoacetanilide
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37 - 47
-
NAT1 is sensitive to heat denaturation and shows a significant loss in activity as temperature is increased from 37C to 47C
37
-
t1/2: 35 h NAT2 wild-type, 3.5 h Cys44Gly-mutant, 0.5 h Cys223Gly-mutant
40 - 47
-
NAT enzymes unfold cooperatively with concomitant loss of activity at 40-47C
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-mercaptoethanol stabilizes
-
cysteine stabilizes
-
glycerol and albumin stabilize
-
thioglycolate stabilizes
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-60C, 60-80% loss of activity after 3 weeks
-
-60C, at least 3 weeks in the presence of 2-mercaptoethanol, thioglycolate or cysteine
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native enzyme partially by subcellular fractionation
-
Ni-NTA resin column chromatography, and gel filtration
-
by using chromatographic purification. Yield: 2.8 mg of homogeneous NAT2 from 2 L of cell culture
-
His-select nickel resin column chromatography
-
native enzyme partially by subcellular fractionation
-
Ni-NTA affinity column chromatography, and gel filtration
-
Ni-NTA column chromatography
-
recombinant His-tagged isozyme NAT1 from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
-
recombinant wild-type and mutant NAT1 from Escherichia coli
-
using Ni-NTA chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3)CodonPlus-RIL cells
-
expression in Escherichia coli
isozyme NAT2, DNA and amino acid sequence determination and analysis, expression of wild-type and mutants in Escherichia coli strain JM105
-
isozyme NAT2, expression in Escherichia coli strain DJ2002
-
2 genes, NAT1 and 2, encoding enzyme proteins, transiently expressed in cultured monkey kidney COS-1 cells
-
; NAT1 is recombinantly expressed
-
a series of constructs is cloned into the pGL3-enhancer
expressed as a His-tagged fusion protein in Escherichia coli; into the pET28a vector for expression in Escherichia coli BL21DE3 cells
-
expressed in Escherichia coli as a His-tagged fusion protein
-
expressed in Escherichia coli BL21(DE3) cells
-
expressed in Escherichia coli JM105 cells
-
expressed in Escherichia coli Rosetta(DE3)pLysS cells
-
expression in Escherichia coli
expression of His-tagged isozyme NAT1 in Escherichia coli strain BL21(DE3)
-
expression of wild-type and mutant NAT1 in Escherichia coli
-
gene NAT1, DNA and amino acid sequence determination and analysis, genetic organization, several splice variants of the NAT1 gene that are expressed from different promoters, expression analysis, the NAT1 gene is located on chromosome 8 at 8p21-22, a region known to be deleted in many human cancers
-
gene NAT1, DNA and amino acid sequence determnination and analysis, quantitative expression analysis
human NAT1 and NAT2 genes located on chromosome 8p22
-
human wild-type NAT2 is overexpressed as a dihydrofolate reductase fusion protein containing a TEV protease-sensitive linker
-
into the pKK223-3 bacterial expression vector for transformation of Escherichia coli JM105 cells
-
NAT1 and NAT2, expressed in Escherichia coli XA90
-
NAT1, DNA and amino acid sequence determination and analysis, exon composition, expression analysis, identification of an alternative NAT1 promoter lying 51.5 kb upstream of the NAT1 ORF, all NAT1 P3 mRNAs included 5'-untranslated region internal exons of 61 and 175 nucleotides in addition to the 79 nucleotide 5'-untranslated region exon present in P1 mRNA CAP-dependent amplification of 50-P3 mRNA termini defined an 84 base pair transcription start region in which most start sites are centrally clustered, overview
-
over-expressed in Salmonella typhimurium umu strain
-
overexpression in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
5-fluorouracil decreases N-acetyltransferase expression
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E8G
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
F192Y
-
site-directed mutagenesis, the NAT2 mutant shows highly reduced activity compared to the wild-type enzyme
H43R
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
I32V
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
K13R
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
K141E
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
L239F
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
L69P
-
site-directed mutagenesis, the NAT2 mutant shows highly reduced activity compared to the wild-type enzyme
L74P
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
Q133R
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
R64Q
structural basis of the effects of the common genetic polymorphism on NAT2 activity, enzyme and active site structure analysis, phenotype, overview
S102C
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
T250P
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
Y190C
-
site-directed mutagenesis, the NAT2 mutant shows highly reduced activity compared to the wild-type enzyme
Y190F
-
site-directed mutagenesis, the NAT2 mutant shows reduced activity compared to the wild-type enzyme
A434C
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
A54V
-
activity with 2-aminofluorene is about 10% of the wild-type activity
A752T
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
A803G
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
C223G
-
NAT2, enzymatically active, markedly reduced in vitro stability
C44G
-
NAT2, enzymatically active, markedly reduced in vitro stability
C481T
-
NAT2 single nucleotide polymorphism
C559T
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
C97T
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
D122N
single nucleotide polymorphism, evaluation of functional effect based on crystal strucutre, PDB 2PFR
D251G
-
activity with 2-aminofluorene is about 15% of the wild-type activity
E167K
single nucleotide polymorphism, evaluation of functional effect based on crystal strucutre, PDB 2PFR. Reduction in maximum activity
E203D
-
609T, single nucleotide polymorphism, point mutation in the arylamine N-acetyltransferase 2 gene, effect missense
F202L
-
activity with 2-aminofluorene is about 20% of the wild-type activity
G364A
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
G499A
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
G560A
-
single nucleotide polymorphism (SNP) found in human, resulting in a decreased activity of enzyme
I238T
-
activity with 2-aminofluorene is about 30% of the wild-type activity, the KM-value for 2-aminofluorene is 1.3fold higher than the wild-type value
K100E
-
the mutation significantly increases the Ka value for acetyl-CoA without changing the Kb value for the acetyl acceptor 4-aminobenzoate
K100L
-
the mutation significantly increases the Ka value for acetyl-CoA without changing the Kb value for the acetyl acceptor 4-aminobenzoate
K100R
-
the mutation significantly decreases the Ka value for acetyl-CoA without changing the Kb value for the acetyl acceptor 4-aminobenzoate
K185N
-
activity with 2-aminofluorene is about 35% of the wild-type activity, the KM-value for 2-aminofluorene is 1.5fold higher than the wild-type value
K282T
single nucleotide polymorphism, evaluation of functional effect based on crystal strucutre, PDB 2PFR
L135V
-
403G, single nucleotide polymorphism, point mutation in the arylamine N-acetyltransferase 2 gene, effect missense
L137F
single nucleotide polymorphism, evaluation of functional effect based on crystal strucutre, PDB 2PFR
L181A
-
activity with 2-aminofluorene is about 80% of the wild-type activity
L194R
-
activity with 2-aminofluorene is about 30% of the wild-type activity
L24I
-
70A, single nucleotide polymorphism, point mutation in the arylamine N-acetyltransferase 2 gene, effect missense
L40H
-
activity with 2-aminofluorene is about 5% of the wild-type activity
M205V
-
activity with 2-aminofluorene is about 40% of the wild-type activity
N172I
-
activity with 2-aminofluorene is about 20% of the wild-type activity, the KM-value for 2-aminofluorene is 3.6fold higher than the wild-type value
N245I
-
activity with 2-aminofluorene is about 85% of the wild-type activity, the KM-value for 2-aminofluorene is 1.3fold higher than the wild-type value
NAT2*12A.U4
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*13.U1
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U1
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U2
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U3
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U5
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U6
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*4.U7
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*5B.U1
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*5B.U4
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*6A.U1
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*7B.U2
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
NAT2*7B.U3
-
polymorphism, proposed new nomenclature composed of haplotype in the promoter region and conventional NAT2 haplotype in the coding region
P228L
-
683T, single nucleotide polymorphism, point mutation in the arylamine N-acetyltransferase 2 gene, effect missense
P96L
-
activity with 2-aminofluorene is slightly higher than wild-type activity
Q145P
single nucleotide polymorphism, evaluation of functional effect based on crystal strucutre, PDB 2PFR. Reduction in both N- and O-acetyltransferase catalytic activitiy
Q226R
-
activity with 2-aminofluorene is about 15% of the wild-type activity
R127S
-
mutant shows a 42fold decreased affinity for the NAT1-selective substrate p-aminobenzoic acid
S125F/S127R/S129Y
-
mutation of all three Ser residues 125, 127 and 129 to those normally present in NAT1 is required to produce the low affinity for sulfamethazine approximating that of native NAT1
T198A
-
activity with 2-aminofluorene is about 50% of the wild-type activity
T207S
-
activity with 2-aminofluorene is slightly higher than wild-type activity
V146A
-
activity with 2-aminofluorene is about 50% of the wild-type activity
V280M
-
838A, single nucleotide polymorphism, point mutation in the arylamine N-acetyltransferase 2 gene, effect missense
W77R
-
activity with 2-aminofluorene is about 25% of the wild-type activity, the KM-value for 2-aminofluorene is 1.3fold higher than the wild-type value
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
inhibitors of NAT enzymes may be valuable as chemopreventive agents
drug development
-
inhibitors of NAT enzymes may be valuable as chemopreventive agents
medicine
molecular biology