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Literature summary extracted from
- Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis (2010), Bioorg. Med. Chem. Lett., 20, 6306-6309.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 4.1.3.36 | - |
Mycobacterium tuberculosis |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 4.1.3.36 | (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 | Mycobacterium tuberculosis |  |
| 4.1.3.36 | (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 | Mycobacterium tuberculosis | |
| 4.1.3.36 | (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 | Mycobacterium tuberculosis | |
| 4.1.3.36 | (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 | Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | - |
Mycobacterium tuberculosis | |
| 4.1.3.36 | methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate | - |
Mycobacterium tuberculosis | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 4.1.3.36 | Mycobacterium tuberculosis | - |
- |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 4.1.3.36 | - |
Mycobacterium tuberculosis |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 4.1.3.36 | o-succinylbenzoyl-CoA | - |
Mycobacterium tuberculosis | 1,4-dihydroxy-2-naphthoyl-CoA + H2O | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 4.1.3.36 | hexamer | - |
Mycobacterium tuberculosis |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 4.1.3.36 | 1,4-dihydroxy-2-naphthoyl-CoA synthase | - |
Mycobacterium tuberculosis |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 4.1.3.36 | 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 | Mycobacterium tuberculosis | |
| 4.1.3.36 | 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 | Mycobacterium tuberculosis | |
| 4.1.3.36 | 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 | Mycobacterium tuberculosis | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 4.1.3.36 | 0.01 | - |
non-competitive inhibitor Ki' = 0.067 mM, pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0179 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-[6-(ethylsulfonyl)-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene]ethanoate | |
| 4.1.3.36 | 0.0182 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(7-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0203 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(7-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0231 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(6-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0241 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(5-methyl-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.027 | - |
non-competitive inhibitor Ki' = 0.0101 mM, pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(6-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0282 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(6-nitro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.03 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(7-fluoro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0357 | - |
pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(7-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
| 4.1.3.36 | 0.0463 | - |
non-competitive inhibitor Ki' = 0.0185 mM, pH not specified in the publication, temperature not specified in the publication | Mycobacterium tuberculosis | methyl (2Z)-(6-chloro-2-oxo-2H-1,4-benzoxazin-3(4H)-ylidene)ethanoate | |
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