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Literature summary extracted from

  • Cho, Y.; Ioerger, T.R.; Sacchettini, J.C.
    Discovery of novel nitrobenzothiazole inhibitors for Mycobacterium tuberculosis ATP phosphoribosyl transferase (HisG) through virtual screening (2008), J. Med. Chem., 51, 5984-5992.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
2.4.2.17 drug development HisG represents a potential drug target for tuberculosis Mycolicibacterium smegmatis
2.4.2.17 drug development HisG represents a potential drug target for tuberculosis Mycobacterium tuberculosis

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.4.2.17 HisG co-crystallized with compound 6, to 2.9 A resolution Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.4.2.17 (4E)-4-[(4-chlorophenyl)(hydroxy)methylidene]-1-(pyridin-3-ylmethyl)-5-(3,4,5-trimethoxyphenyl)pyrrolidine-2,3-dione binds to the cavity between the domains I and II. The terminal chlorobenzoyl group of 1 makes hydrophobic interactions with the amphiphilic pocket near the phosphoribosyl pyrophosphate binding site Mycobacterium tuberculosis
2.4.2.17 1-[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfanyl]-3-(1,3-thiazol-2-yl)propan-2-one most potent inhibitor, spans the PR-ATP binding site, exhibits greater than 50% inhibition at 0.01 mM, 40% inhibition at 0.001 mM Mycobacterium tuberculosis
2.4.2.17 2-([7-[(3-hydroxyphenyl)amino]-4-nitro-2,1,3-benzoxadiazol-5-yl]amino)-5-nitrophenol exhibits 46% inhibition Mycobacterium tuberculosis
2.4.2.17 2-([7-[(3-hydroxyphenyl)amino]-4-nitro-2,1,3-benzoxadiazol-5-yl]amino)-5-nitrophenol has whole-cell activity at 0.012 mM Mycolicibacterium smegmatis
2.4.2.17 2-[(2-bromo-3,5-dinitrophenyl)carbonyl]-N-phenylhydrazinecarboxamide exhibits 71% inhibition Mycobacterium tuberculosis
2.4.2.17 2-[(2-bromo-3,5-dinitrophenyl)carbonyl]-N-phenylhydrazinecarboxamide has whole-cell activity at 0.025 mM Mycolicibacterium smegmatis
2.4.2.17 4-methoxybenzyl 2-methyl-5-oxo-4,7-dithiophen-2-yl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate interacts with the phosphoribosyl diphosphate binding site but less strongly compared to compound 6 , exhibits greater than 50% inhibition at 0.01 mM Mycobacterium tuberculosis
2.4.2.17 ethyl [(6-nitro-1,3-benzothiazol-2-yl)amino](oxo)acetate exhibits 39% inhibition Mycobacterium tuberculosis
2.4.2.17 N-[3-[(6-nitro-1,3-benzothiazol-2-yl)amino]-3-oxo-1-phenylpropyl]benzamide occupies only the phosphoribosyl diphosphate binding site, exhibits greater than 50% inhibition at 0.01 mM, 35% inhibition at 0.001 mM Mycobacterium tuberculosis

Organism

EC Number Organism UniProt Comment Textmining
2.4.2.17 Mycobacterium tuberculosis P9WMN1
-
-
2.4.2.17 Mycobacterium tuberculosis H37Rv P9WMN1
-
-
2.4.2.17 Mycolicibacterium smegmatis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.4.2.17 ATP + 5-phospho-alpha-D-ribose 1-diphosphate
-
 Mycobacterium tuberculosis 1-(5-phospho-D-ribosyl)-ATP + diphosphate
-
 ?
2.4.2.17 ATP + 5-phospho-alpha-D-ribose 1-diphosphate
-
 Mycobacterium tuberculosis H37Rv 1-(5-phospho-D-ribosyl)-ATP + diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.4.2.17 ATP phosphoribosyl transferase
-
 Mycolicibacterium smegmatis
2.4.2.17 ATP phosphoribosyl transferase
-
 Mycobacterium tuberculosis
2.4.2.17 ATP-PRTase
-
 Mycolicibacterium smegmatis
2.4.2.17 ATP-PRTase
-
 Mycobacterium tuberculosis
2.4.2.17 HisG
-
 Mycolicibacterium smegmatis
2.4.2.17 HisG
-
 Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
2.4.2.17 0.002
-
 1-[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfanyl]-3-(1,3-thiazol-2-yl)propan-2-one
-
 Mycobacterium tuberculosis
2.4.2.17 0.002
-
 N-[3-[(6-nitro-1,3-benzothiazol-2-yl)amino]-3-oxo-1-phenylpropyl]benzamide
-
 Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
2.4.2.17 0.004
-
-
 Mycobacterium tuberculosis 1-[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfanyl]-3-(1,3-thiazol-2-yl)propan-2-one
2.4.2.17 0.0055
-
-
 Mycobacterium tuberculosis 4-methoxybenzyl 2-methyl-5-oxo-4,7-dithiophen-2-yl-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
2.4.2.17 0.006
-
-
 Mycobacterium tuberculosis N-[3-[(6-nitro-1,3-benzothiazol-2-yl)amino]-3-oxo-1-phenylpropyl]benzamide
2.4.2.17 0.0119
-
-
 Mycobacterium tuberculosis (4E)-4-[(4-chlorophenyl)(hydroxy)methylidene]-1-(pyridin-3-ylmethyl)-5-(3,4,5-trimethoxyphenyl)pyrrolidine-2,3-dione
2.4.2.17 0.0139
-
-
 Mycobacterium tuberculosis 2-[(2-bromo-3,5-dinitrophenyl)carbonyl]-N-phenylhydrazinecarboxamide