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Literature summary extracted from

  • Tan, X.; Wang, P.; Nian, S.; Wang, G.
    Design and synthesis of amide derivatives as S-adenosyl-L-homocysteine hydrolase inhibitors (2014), Chem. Pharm. Bull., 62, 112-117.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.13.2.1 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-fluorophenyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 4.56% inhibition at 0.0025 mM; 8.23% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)-amino)-N-(isoindolin-2-yl)-N-methylacetamide 4.89% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 30.19% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 27.15% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 85.72% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 86.56% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 19.23% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(diethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 20.16% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(ethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 79.46% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((4-(1H-pyrrol-1-yl)phenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 21.46% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 2-((4-fluorophenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)-amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide 2.63% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 3-deazaadenosine 35.37% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 aristeromycin 98.35% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 DZ2002
-
Mycobacterium tuberculosis
3.13.2.1 N-(isoindolin-2-yl)-N-methyl-2-((1-methyl-1H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-acetamide 54.24% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 N-(isoindolin-2-yl)-N-methyl-2-((2-methyl-2H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl) ethyl)amino)ethyl)amino)-acetamide 38.24% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 N-(isoindolin-2-yl)-N-methyl-2-((2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)(4-tolyl)amino)acetamide 6.97% inhibition at 0.0025 mM Mycobacterium tuberculosis
3.13.2.1 neplanocin A
-
Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.13.2.1 S-adenosyl-L-homocysteine + H2O Mycobacterium tuberculosis
-
L-homocysteine + adenosine
-
r

Organism

EC Number Organism UniProt Comment Textmining
3.13.2.1 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.13.2.1 S-adenosyl-L-homocysteine + H2O
-
Mycobacterium tuberculosis L-homocysteine + adenosine
-
r

Synonyms

EC Number Synonyms Comment Organism
3.13.2.1 S-adenosyl-L-homocysteine hydrolase
-
Mycobacterium tuberculosis
3.13.2.1 SAHase
-
Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.13.2.1 0.00044
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.00048
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.00049
-
at pH 8.0 and 37°C Mycobacterium tuberculosis aristeromycin
3.13.2.1 0.00073
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(ethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.00203
-
at pH 8.0 and 37°C Mycobacterium tuberculosis N-(isoindolin-2-yl)-N-methyl-2-((1-methyl-1H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-acetamide
3.13.2.1 0.00413
-
at pH 8.0 and 37°C Mycobacterium tuberculosis N-(isoindolin-2-yl)-N-methyl-2-((2-methyl-2H-indazol-5-yl)(2-oxo-2-((2-(piperidin-1-yl) ethyl)amino)ethyl)amino)-acetamide
3.13.2.1 0.00552
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 3-deazaadenosine
3.13.2.1 0.00761
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(1-methyl-1H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.01212
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((4-(1H-pyrrol-1-yl)phenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.01408
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((4-(1H-pyrrol-1-yl)phenyl)(2-((2-(diethylamino)-ethyl)amino)-2-oxoethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.0156
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(ethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.02534
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)-(2-methyl-2H-indazol-5-yl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.07882
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-fluorophenyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.1019
-
at pH 8.0 and 37°C Mycobacterium tuberculosis N-(isoindolin-2-yl)-N-methyl-2-((2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)(4-tolyl)amino)acetamide
3.13.2.1 0.214
-
at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-tolyl)-amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.5
-
IC50 above 0.5 mM, at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((2-((2-(diethylamino)ethyl)amino)-2-oxoethyl)(4-fluorophenyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide
3.13.2.1 0.5
-
IC50 above 0.5 mM, at pH 8.0 and 37°C Mycobacterium tuberculosis 2-((4-fluorophenyl)(2-oxo-2-((2-(piperidin-1-yl)ethyl)-amino)ethyl)amino)-N-(isoindolin-2-yl)-N-methylacetamide