4.1.3.36: 1,4-dihydroxy-2-naphthoyl-CoA synthase
This is an abbreviated version!
For detailed information about 1,4-dihydroxy-2-naphthoyl-CoA synthase, go to the full flat file.
Word Map on EC 4.1.3.36
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4.1.3.36
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menaquinone
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tuberculosis
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crotonase
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1,4-dihydroxy-2-naphthoic
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hexamer
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o-succinylbenzoyl-coa
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o-succinylbenzoic
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oxyanion
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induced-fit
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claisen
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reorientation
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tetrahedral
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osb-coa
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phlei
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5'-triphosphate
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trimer-trimer
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enzyme-ligand
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medicine
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drug development
- 4.1.3.36
- menaquinone
- tuberculosis
- crotonase
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1,4-dihydroxy-2-naphthoic
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hexamer
- o-succinylbenzoyl-coa
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o-succinylbenzoic
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oxyanion
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induced-fit
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claisen
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reorientation
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tetrahedral
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osb-coa
- phlei
- 5'-triphosphate
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trimer-trimer
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enzyme-ligand
- medicine
- drug development
Reaction
Synonyms
1,4-dihydroxy-2-naphthoate synthetase, 1,4-dihydroxy-2-naphthoyl coenzyme A synthase, 1,4-dihydroxy-2-naphthoyl-CoA synthase, 1,4-dihydroxy-2-naphthoyl-coenzyme synthase, DHNA synthetase, DHNA-CoA synthase, dihydroxynaphthoate synthase, Dihydroxynaphthoic acid synthetase, MenB, naphthoate synthase, naphthoate synthase (MenB), Rv0548c, synthase, 1,4-dihydroxy-2-naphthoate
ECTree
4.1.3.36 1,4-dihydroxy-2-naphthoyl-CoA synthaseAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 4.1.3.36 - 1,4-dihydroxy-2-naphthoyl-CoA synthase
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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
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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
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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
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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
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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
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methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate
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methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate
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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
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1-hydroxy-2-naphthoyl-CoA
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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
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additional information
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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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