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Information on EC 3.5.1.137 - N-methylcarbamate hydrolase
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3.5.1.137 N-methylcarbamate hydrolaseIUBMB Comments
The enzyme catalyses the first step in the degradation of several carbamate insecticides such as carbaryl, carbofuran, isoprocarb, propoxur, aldicarb and oxamyl. It catalyses the cleavage of the ester bond to release N-methylcarbamate, which spontaneously hydrolyses to methylamine and CO2. The enzymes from several Gram-negative bacteria were shown to be located in the periplasm.
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Word Map
- 3.5.1.137
-
pesticide
-
insecticide
- aldicarb
- 1-naphthol
- oxamyl
- propoxur
- isoprocarb
- gentisate
- fenobucarb
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novosphingobium
-
achromobacter
-
sphingobium
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nematicide
The enzyme appears in viruses and cellular organisms
Synonyms
carbaryl hydrolase, carbamate hydrolase, carbofuran hydrolase, carbamate c-n hydrolase, methyl carbamate-degrading hydrolase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ameH
carbamate C-N hydrolase
carbamate hydrolase
carbaryl hydrolase
carbofuran hydrolase
cehA
cfdJ
mcbA
MCD
methomyl hydrolase
carbaryl hydrolase
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-
-
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carbofuran hydrolase
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-
-
-
cehA
-
-
-
-
cfdJ
-
-
-
-
mcbA
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
an N-methyl carbamate ester + H2O = an alcohol + methylamine + CO2
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-
-
-
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PATHWAY SOURCE
PATHWAYS
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, , ,
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SYSTEMATIC NAME
IUBMB Comments
N-methyl carbamate ester hydrolase
The enzyme catalyses the first step in the degradation of several carbamate insecticides such as carbaryl, carbofuran, isoprocarb, propoxur, aldicarb and oxamyl. It catalyses the cleavage of the ester bond to release N-methylcarbamate, which spontaneously hydrolyses to methylamine and CO2. The enzymes from several Gram-negative bacteria were shown to be located in the periplasm.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-nitrophenyl dimethylcarbamate + H2O
? + methylamine + CO2
-
-
-
-
?
an N-methyl carbamate ester + H2O
an alcohol + methylamine + CO2
-
-
-
-
?
carbofuran + H2O
2,3-dihydro-2,2-dimethyl-7-benzofuranol + methylamine + CO2
-
i.e. 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-methylcarbamate
-
-
?
dimethyl umbelliferyl phosphate + H2O
umbelliferone + dimethyl phosphate
-
-
-
-
?
methylparathion + H2O
?
i.e. O,O-dimethyl-O-4-nitrophenylthiophosphate
-
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
-
51% activity compared to carbaryl
-
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
-
73% activity compared to carbaryl
-
-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
Aspergillus niger PY168
-
73% activity compared to carbaryl
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-
?
1-naphthyl acetate + H2O
1-naphthol + acetate
Blastobacter sp. M501
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2% activity compared to carbaryl
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-
?
3,5-dimethylphenyl N-methylcarbamate + H2O
?
Blastobacter sp. M501
-
66% activity compared to carbaryl
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-
?
3,5-dimethylphenyl N-methylcarbamate + H2O
?
XMC, 115% activity compared to carbaryl
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-
?
3,5-dimethylphenyl N-methylcarbamate + H2O
? + methylamine + CO2
-
43% activity compared to carbaryl
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-
?
3,5-dimethylphenyl N-methylcarbamate + H2O
? + methylamine + CO2
-
91% activity compared to carbaryl
-
-
?
3,5-dimethylphenyl N-methylcarbamate + H2O
? + methylamine + CO2
Aspergillus niger PY168
-
91% activity compared to carbaryl
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-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
-
80% activity compared to carbaryl
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-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
-
77% activity compared to carbaryl
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-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
Aspergillus niger PY168
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77% activity compared to carbaryl
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-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
Blastobacter sp. M501
-
4% activity compared to carbaryl
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-
?
aldicarb + H2O
? + methylamine + CO2
-
i.e. 2-methyl-2-(methylthio)propionaldehyde O-(N-methylcarbamoyl)oxime
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-
?
aldicarb + H2O
? + methylamine + CO2
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18% activity compared to carbaryl
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-
?
aldicarb + H2O
? + methylamine + CO2
Pseudomonas sp. CRL-OK
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i.e. 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
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-
-
-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
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preferred substrate, 100% activity
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
Aspergillus niger PY168
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preferred substrate, 100% activity
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
Blastobacter sp. M501
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i.e. 1-naphthyl N-methylcarbamate, 100% activity
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
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highest activity
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?
carbaryl + H2O
1-naphthol + methylamine + CO2
Pseudomonas sp. CRL-OK
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i.e. 1-naphthyl N-methylcarbamate
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
best substrate
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-
?
carbaryl + H2O
1-naphthol + methylamine + CO2
i.e. 1-naphthyl N-methylcarbamate, 100% activity
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-
?
carbofuran + H2O
7-phenol + methylamine + CO2
Agrobacterium sp. XWY-2
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51.24% activity compared to carbaryl
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?
carbofuran + H2O
? + methylamine + CO2
Pseudomonas sp. CRL-OK
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i.e. 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-methylcarbamate
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-
?
carbofuran + H2O
carbofuran phenol + methylamine + CO2
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83% activity compared to carbaryl
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?
carbofuran + H2O
carbofuran phenol + methylamine + CO2
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the extent of hydrolysis of carbofuran is about 0.6fold compared to carbaryl
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?
carbofuran + H2O
carbofuran phenol + methylamine + CO2
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?
fenobucarb + H2O
?
Blastobacter sp. M501
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i.e 2-S-butylphenyl N-methylcarbamate, 2% activity compared to carbaryl
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?
fenobucarb + H2O
?
i.e 2-s-butylphenyl N-methylcarbamate, 11% activity compared to carbaryl
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-
?
fenobucarb + H2O
? + methylamine + CO2
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32% activity compared to carbaryl
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?
isoprocarb + H2O
?
Agrobacterium sp. XWY-2
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i.e. 2-isopropylphenyl N-methylcarbamate, 2% activity compared to carbaryl
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?
isoprocarb + H2O
?
Blastobacter sp. M501
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i.e. 2-isopropylphenyl N-methylcarbamate, 2% activity compared to carbaryl
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?
isoprocarb + H2O
?
i.e. 2-isopropylphenyl N-methylcarbamate, 21% activity compared to carbaryl
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?
isoprocarb + H2O
? + methylamine + CO2
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43% activity compared to carbaryl
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-
?
isoprocarb + H2O
? + methylamine + CO2
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the extent of hydrolysis of carbofuran is about 0.5fold compared to carbaryl
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?
methomyl + H2O
methyl (1E)-N-hydroxyethanimidothioate + methylamine + CO2
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-
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?
methomyl + H2O
methyl (1E)-N-hydroxyethanimidothioate + methylamine + CO2
Aminobacter aminovorans MDW-2
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?
metolcarb + H2O
?
Blastobacter sp. M501
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i.e. 3-methylphenyl N-methylcarbamate, 62% activity compared to carbaryl
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?
metolcarb + H2O
?
i.e. 3-methylphenyl N-methylcarbamate, 54% activity compared to carbaryl
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-
?
metolcarb + H2O
? + methylamine + CO2
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304% activity compared to carbaryl
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?
metolcarb + H2O
? + methylamine + CO2
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87% activity compared to carbaryl
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?
propoxur + H2O
?
Blastobacter sp. M501
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i.e. 2-isopropoxyphenyl N-methylcarbamate, 14% activity compared to carbaryl
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?
propoxur + H2O
?
i.e. 2-isopropoxyphenyl N-methylcarbamate, 9% activity compared to carbaryl
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?
propoxur + H2O
? + methylamine + CO2
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54% activity compared to carbaryl
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?
xylylcarb + H2O
?
Blastobacter sp. M501
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i.e. 3,4-dimethylphenyl N-methylcarbamate, 88% activity compared to carbaryl
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?
xylylcarb + H2O
?
i.e. 3,4-dimethylphenyl N-methylcarbamate, 61% activity compared to carbaryl
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?
xylylcarb + H2O
? + methylamine + CO2
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66% activity compared to carbaryl
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?
xylylcarb + H2O
? + methylamine + CO2
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93% activity compared to carbaryl
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?
additional information
?
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no activity with diethyl umbelliferyl phosphate, chlorpyrifos and parathion
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-
additional information
?
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the enzyme is unable to hydrolyze parathion (O,O-diethyl O-(4-nitrophenyl) phosphorothioate), S-ethyl dipropylthiocarbamate, or chlorpropham (isopropyl 3-chlorocarbanilate)
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additional information
?
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the purified enzyme has no urease activity
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additional information
?
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Agrobacterium sp. XWY-2
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the enzyme does not hydrolyze N-acetyl-4-aminophenol or methomyl
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-
additional information
?
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the enzyme shows no catalytic activity on any carbamate pesticide other than methomyl, including carbaryl, isoprocarb, fenobucarb, propoxur, aldicarb, carbofuran, and oxamyl
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-
-
additional information
?
-
Aminobacter aminovorans MDW-2
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the enzyme shows no catalytic activity on any carbamate pesticide other than methomyl, including carbaryl, isoprocarb, fenobucarb, propoxur, aldicarb, carbofuran, and oxamyl
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-
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additional information
?
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the enzyme is not able to hydrolyze chloropropham, fenobucarb, propoxur, and isoprocarb
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additional information
?
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hydrolase activity is undetectable with chloropropham, S-ethyl dipropylthiocarbamate, and parathion
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additional information
?
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Aspergillus niger PY168
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hydrolase activity is undetectable with chloropropham, S-ethyl dipropylthiocarbamate, and parathion
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additional information
?
-
Blastobacter sp. M501
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hydrolase activity is not detected with the substrates of fenitrothion, methylparathion, paraoxon, chloropropham, swep, propanil, and linuron
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-
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additional information
?
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no activity with carbofuran and aldicarb
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additional information
?
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Pseudomonas sp. 50432
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the purified enzyme does not hydrolyze 2-nitrophenyl dimethylcarbamate
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-
-
additional information
?
-
Pseudomonas sp. CRL-OK
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no activity with isopropyl 3-chlorocarbanilate, S-ethyl N,N-dipropylthiocarbamate, and 2-nitrophenyldimethylcarbamate
-
-
-
additional information
?
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the enzyme cannot hydrolyze N-acetyl 4-aminophenol, methomyl and oxamyl
-
-
-
additional information
?
-
hydrolase activity is undetectable with the substrates of carbofuran and chloropropham
-
-
-
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
an N-methyl carbamate ester + H2O
an alcohol + methylamine + CO2
-
-
-
-
?
carbofuran + H2O
7-phenol + methylamine + CO2
Agrobacterium sp. XWY-2
-
51.24% activity compared to carbaryl
-
-
?
isoprocarb + H2O
?
Agrobacterium sp. XWY-2
-
i.e. 2-isopropylphenyl N-methylcarbamate, 2% activity compared to carbaryl
-
-
?
additional information
?
-
Agrobacterium sp. XWY-2
-
the enzyme does not hydrolyze N-acetyl-4-aminophenol or methomyl
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
Mn2+
Ni2+
Zn2+
additional information
Mn2+
-
required for enzyme activity. The enzyme preparation is stabilized at all stages of the purification regimen by manganese ions
Ni2+