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Information on EC 4.1.3.36 - 1,4-dihydroxy-2-naphthoyl-CoA synthase
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EC Tree
4.1.3.36 1,4-dihydroxy-2-naphthoyl-CoA synthaseIUBMB Comments
This enzyme is involved in the synthesis of 1,4-dihydroxy-2-naphthoate, a branch point metabolite leading to the biosynthesis of menaquinone (vitamin K2, in bacteria), phylloquinone (vitamin K1 in plants), and many plant pigments.
The coenzyme A group is subsequently removed from the product by EC 3.1.2.28, 1,4-dihydroxy-2-naphthoyl-CoA hydrolase.
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Word Map
- 4.1.3.36
- menaquinone
- tuberculosis
- crotonase
-
1,4-dihydroxy-2-naphthoic
-
hexamer
- o-succinylbenzoyl-coa
-
o-succinylbenzoic
-
oxyanion
-
induced-fit
-
claisen
-
reorientation
-
tetrahedral
-
osb-coa
- phlei
- 5'-triphosphate
-
trimer-trimer
-
enzyme-ligand
- medicine
- drug development
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
naphthoate synthase, 1,4-dihydroxy-2-naphthoyl-coa synthase, dihydroxynaphthoate synthase, dhna-coa synthase, naphthoate synthase (menb), dhna synthetase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,4-dihydroxy-2-naphthoyl coenzyme A synthase
1,4-dihydroxy-2-naphthoyl-CoA synthase
DHNA synthetase
DHNA-CoA synthase
Dihydroxynaphthoic acid synthetase
-
-
-
-
MenB
Rv0548c
synthase, 1,4-dihydroxy-2-naphthoate
-
-
-
-
DHNA synthetase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
-
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O
the enzyme is an essential enzyme in vitamin K biosynthesis, which is responsible for conversion of o-succinylbenzoyl-CoA to 1,4-dihydroxy-2-naphthoyl-CoA via catalysis of a multiple-step intramolecular Claisen condensation reaction, proposed reaction mechanism, overview
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O
the enzyme is an essential enzyme in vitamin K biosynthesis, which is responsible for conversion of o-succinylbenzoyl-CoA to DHNACoA via catalysis of a multiple-step intramolecular Claisen condensation reaction, proposed reaction mechanism, overview
-
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O
unique induced-fit catalytic mechanism which involves intersubunit interactions, overview
-
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA = 1,4-dihydroxy-2-naphthoyl-CoA + H2O
unique induced-fit catalytic mechanism which involves intersubunit interactions, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Claisen condensation
cleavage of 3-hydroxy acid
cleavage of 3-hydroxy acid
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
-
-
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SYSTEMATIC NAME
IUBMB Comments
4-(2-carboxyphenyl)-4-oxobutanoyl-CoA dehydratase (cyclizing)
This enzyme is involved in the synthesis of 1,4-dihydroxy-2-naphthoate, a branch point metabolite leading to the biosynthesis of menaquinone (vitamin K2, in bacteria), phylloquinone (vitamin K1 in plants), and many plant pigments.
The coenzyme A group is subsequently removed from the product by EC 3.1.2.28, 1,4-dihydroxy-2-naphthoyl-CoA hydrolase.
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CAS REGISTRY NUMBER
COMMENTARY
72506-71-9
-
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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-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
formation of a structural motif like an oxyanion hole for orientation of the o-succinylbenzoate substrate and stabilization of the oxyanion intermediate in the intramolecular Claisen condensation, which involves a conserved tyrosine residue in the A-loop. via induced fit
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
catalyzes an intramolecular Claisen condensation reaction leading to the formation of 1,4-dihydroxy-2-naphthoyl-CoA from o-succinylbenzoate, the enzyme substrate is chemically unstable
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
catalyzes an intramolecular Claisen condensation reaction leading to the formation of 1,4-dihydroxy-2-naphthoyl-CoA from o-succinylbenzoate, the enzyme substrate is chemically unstable
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
formation of a structural motif like an oxyanion hole for orientation of the o-succinylbenzoate substrate and stabilization of the oxyanion intermediate in the intramolecular Claisen condensation, which involves a conserved tyrosine residue in the A-loop via induced fit
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
highly specific, no substrates are 2-(3'-carboxypropionyl)benzoyl-CoA or 4-(2'-carboxyphenyl)4-oxobutyryl-diCoA
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
highly specific, no substrates are 2-(3'-carboxypropionyl)benzoyl-CoA or 4-(2'-carboxyphenyl)4-oxobutyryl-diCoA
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
highly specific, no substrates are 2-(3'-carboxypropionyl)benzoyl-CoA or 4-(2'-carboxyphenyl)4-oxobutyryl-diCoA
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
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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
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
formation of a structural motif like an oxyanion hole for orientation of the o-succinylbenzoate substrate and stabilization of the oxyanion intermediate in the intramolecular Claisen condensation, which involves a conserved tyrosine residue in the A-loop. via induced fit
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoate + CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
formation of a structural motif like an oxyanion hole for orientation of the o-succinylbenzoate substrate and stabilization of the oxyanion intermediate in the intramolecular Claisen condensation, which involves a conserved tyrosine residue in the A-loop via induced fit
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
1,4-dihydroxy-2-naphthoyl-CoA + H2O
-
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
o-succinylbenzoyl-CoA
?
-
pathway in menaquinone biosynthesis, i.e. vitamin K2, cf. EC 6.2.1.26
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
bicarbonate
additional information
bicarbonate
-
the enzyme from Escherichia coli is a type I enzyme, which is dependent on exogenous bicarbonate for catalytic activity. The bicarbonate cofactor is bound to the enzyme active site at a position equivalent to that of the side chain carboxylate of an aspartate residue conserved among bicarbonate-insensitive DHNA-CoA synthases, binding site structure, overview
bicarbonate
the enzyme from Synechocystis is a type I enzyme, type I enzymes are dependent on exogenous bicarbonate for catalytic activity. The bicarbonate cofactor is bound to the enzyme active site at a position equivalent to that of the side chain carboxylate of an aspartate residue conserved among bicarbonate-insensitive DHNA-CoA synthases, binding site structure, overview
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
-
68.4% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate , pH not specified in the publication, temperature not specified in the publication
(3Z)-3-(3,3-dimethyl-2-oxobutylidene)-6-(ethylsulfonyl)-3,4-dihydro-2H-1,4-benzoxazin-2-one
-
60.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
(3Z)-6-chloro-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
-
98% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
(3Z)-6-methyl-3-(4-methyl-2-oxopentylidene)-3,4-dihydro-2H-1,4-benzoxazin-2-one
-
77.3% inhibition at 0.125 mg/ml, 0.00015 mM o-succinylbenzoate, pH not specified in the publication, temperature not specified in the publication
4-(2-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
half-life at 25°C, pH 7.4, is 0.4 h
4-(2-methoxyphenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
half-life at 25°C, pH 7.4, is 11.6 h
4-(4-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
half-life at 25°C, pH 7.4, is 6.8 h
4-(4-fluorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
half-life at 25°C, pH 7.4, is 12.2 h
4-oxo-2-[[(1S)-1-phenylethyl]amino]-4-[2-(trifluoromethyl)phenyl]butanoic acid
half-life at 25°C, pH 7.4, is 0.2 h
4-oxo-4-chlorophenylbutenoyl methyl ester
penetrates the cell where it is hydrolyzed and reacts with CoA to generate the active antibacterial compound, mechanism, overview
4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid
half-life at 25°C, pH 7.4, is 11.6 h
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
-
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
-
-
O5'-(4-(3-[2-[2-((R)-3-hydroxy-4-(trimethylammonio)-1-oxo-butyl)sulfanyl-ethylcarbamoyl]-ethylcarbamoyl]-(R)-3-hydroxy-2,2-dimethyl-propyl)-1-hydroxy-3-oxido-1,3-dioxo-2,4-dioxa-1,3-diphosphabut-1-yl) 3'-phospho-adenosine
-
-
1-hydroxy-2-naphthoyl-CoA
-
a product analogue, protein-ligand interactions, complex structure, overview
1-hydroxy-2-naphthoyl-CoA
a product analogue, protein-ligand interactions, complex structure, overview
salicyloyl-CoA
protein-ligand interactions, complex structure, overview
additional information
2-amino-4-oxo-4-phenylbutanoate inhibitors are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. No inhibition by 1548L21 at 0.3 mM
-
additional information
-
2-amino-4-oxo-4-phenylbutanoate inhibitors are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. No inhibition by 1548L21 at 0.3 mM
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Tuberculosis
CoA Adducts of 4-Oxo-4-Phenylbut-2-enoates: Inhibitors of MenB from the M. tuberculosis Menaquinone Biosynthesis Pathway.
Tuberculosis
Expression of the naphthoate synthase gene in Mycobacterium tuberculosis in a self-generated oxygen depleted liquid culture system.
Tuberculosis
Ligand-dependent active-site closure revealed in the crystal structure of Mycobacterium tuberculosis MenB complexed with product analogues.
Tuberculosis
Structure of naphthoate synthase (MenB) from Mycobacterium tuberculosis in both native and product-bound forms.
Tuberculosis
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.106
2-(3-carboxypropyl)-benzoyl-CoA
wild type protein protein, pH 7.0, 25°C
0.0031
2-succinylbenzoyl-CoA
D185N mutant protein, pH 7.0, 25°C
0.0048
2-succinylbenzoyl-CoA
D185E mutant protein, pH 7.0, 25°C
0.0224
2-succinylbenzoyl-CoA
wild type protein, pH 7.0, 25°C
0.0402
2-succinylbenzoyl-CoA
S190A mutant protein, pH 7.0, 25°C
0.0028
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, wild-type enzyme
0.0166
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant R267A
0.0197
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant F270A
0.0433
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant K89A
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00025
2-(3-carboxypropyl)-benzoyl-CoA
wild type protein protein, pH 7.0, 25°C
0.00022
2-succinylbenzoyl-CoA
D185N mutant protein, pH 7.0, 25°C
0.0017
2-succinylbenzoyl-CoA
S190A mutant protein, pH 7.0, 25°C
0.0023
2-succinylbenzoyl-CoA
D185E mutant protein, pH 7.0, 25°C
0.462
2-succinylbenzoyl-CoA
wild type protein, pH 7.0, 25°C
0.0027
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant R267A
0.0035
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant F270A
0.021
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, wild-type enzyme
0.038
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant K89A
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0024
2-(3-carboxypropyl)-benzoyl-CoA
wild type protein protein, pH 7.0, 25°C
0.04
2-succinylbenzoyl-CoA
S190A mutant protein, pH 7.0, 25°C
0.07
2-succinylbenzoyl-CoA
D185N mutant protein, pH 7.0, 25°C
0.48
2-succinylbenzoyl-CoA
D185E mutant protein, pH 7.0, 25°C
0.16
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant R267A
0.18
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant F270A
0.89
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, mutant K89A
7.4
o-succinylbenzoate
-
pH 7.0, temperature not specified in the publication, wild-type enzyme
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000049
2-CoA-4-(2,4-dichlorophenyl)-4-oxobutanoic acid
pH 7.4, 25°C
0.000097
2-CoA-4-(2-chlorophenyl)-4-oxobutanoic acid
pH 7.4, 25°C
0.00035
2-CoA-4-(4-dichlorophenyl)-4-oxobutanoic acid
pH 7.4, 25°C
0.0091
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
0.0225
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
non-competitive inhibitor, pH not specified in the publication, temperature not specified in the publication
0.0115
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
-
non-competitive inhibitor , pH not specified in the publication, temperature not specified in the publication
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000106
2-CoA-4-(2,4-dichlorophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.000135
2-CoA-4-(2-bromophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.000103
2-CoA-4-(2-chlorophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.000204
2-CoA-4-(2-fluorophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.000421
2-CoA-4-(2-iodophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0121
2-CoA-4-(2-methoxyphenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.000154
2-CoA-4-(2-nitrophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0141
2-CoA-4-(3-chlorophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.00047
2-CoA-4-(4-dichlorophenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0335
2-CoA-4-(4-methoxyphenyl)-4-oxobutanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.4
3-(2,4-dichlorophenyl)-3-oxopropyl-CoA
Mycobacterium tuberculosis
above, pH 7.4, 25°C
0.0022
4-(2,4-dichlorophenyl)-4-oxobutanoyl-CoA
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0084
4-(2-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.12
4-(2-methoxyphenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
117
4-(4-chlorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0144
4-(4-fluorophenyl)-4-oxo-2-[[(1S)-1-phenylethyl]amino]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0032
4-oxo-2-[[(1S)-1-phenylethyl]amino]-4-[2-(trifluoromethyl)phenyl]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.0527
4-oxo-4-phenyl-2-[[(1S)-1-phenylethyl]amino]butanoic acid
Mycobacterium tuberculosis
pH 7.4, 25°C
0.01
methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
non-competitive inhibitor Ki' = 0.067 mM, pH not specified in the publication, temperature not specified in the publication
0.0241
methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0463
methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
non-competitive inhibitor Ki' = 0.0185 mM, pH not specified in the publication, temperature not specified in the publication
0.027
methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
non-competitive inhibitor Ki' = 0.0101 mM, pH not specified in the publication, temperature not specified in the publication
0.0231
methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0282
methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0357
methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.03
methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0182
methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0203
methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0179
methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE