Literature summary for 3.5.4.4 extracted from

Terasaka, T.; Kinoshita, T.; Kuno, M.; Seki, N.; Tanaka, K.; Nakanishi, I.
Structure-based design, synthesis, and structure-activity relationship studies of novel non-nucleoside adenosine deaminase inhibitors (2004), J. Med. Chem., 47, 3730-3743.

Crystallization (Commentary)

Crystallization (Comment)	Organism
purified intestinal enzyme complexed with 1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)2-butyl]imidazole-4-carboxamide, 1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)2-butyl]imidazole-4-carboxamide, or 1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide, protein solution is mixed with precipitant solution containing 100 mM MES, pH 6.0, 2.1 ammonium sulfate, and 2.5% v/v PEG 400, X-ray diffraction structure determination and analysis at 2.2 A resolution	Bos taurus

Crystallization (Comment)

Organism

purified intestinal enzyme complexed with 1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)2-butyl]imidazole-4-carboxamide, 1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)2-butyl]imidazole-4-carboxamide, or 1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide, protein solution is mixed with precipitant solution containing 100 mM MES, pH 6.0, 2.1 ammonium sulfate, and 2.5% v/v PEG 400, X-ray diffraction structure determination and analysis at 2.2 A resolution

Bos taurus

Inhibitors

Inhibitors	Comment	Organism
1-[(R)-1-hydroxy-4-(1-methyl-5-(3-phenylpropoxy)indol-3-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(5-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-(1-methylbenzimidazol-2-yl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-(3-pyridyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-(4-methylphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(4-(4-methylphenyl)butyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(4-phenylbutoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-1-hydroxy-4-(6-(6-phenylhexanoylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(5-(3-(4-chlorophenyl)propoxyl)-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(5-hexyloxy-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(5-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-(3-(4-chlorophenyl)propoxy)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-acetylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-butoxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-hexanoylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
1-[(R)-4-(6-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
erythro-9-(2-hydroxy-3-nonyl)adenine	i.e. (+)-EHNA	Bos taurus
additional information	structure-based design, synthesis, and structure-activity relationship studies of non-nucleoside adenosine deaminase inhibitors, overview	Bos taurus
pentostatin	-	Bos taurus

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
adenosine + H2O	Bos taurus	-	inosine + NH3	-	ir

Organism

Organism	UniProt	Comment	Textmining
Bos taurus	P56658	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
intestine	-	Bos taurus	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
adenosine + H2O	-	Bos taurus	inosine + NH3	-	ir

Synonyms

Synonyms	Comment	Organism
ADA	-	Bos taurus

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism
0.0000049	-	1-[(R)-4-(5-(3-(4-chlorophenyl)propoxyl)-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.0000075	-	1-[(R)-4-(6-(3-benzylureido)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.0000077	-	1-[(R)-1-hydroxy-4-(6-(5-phenylvalerylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000011	-	1-[(R)-1-hydroxy-4-(6-(3-(1-methylbenzimidazol-2-yl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000012	-	1-[(R)-1-hydroxy-4-(6-(4-phenylbutoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000013	-	1-[(R)-4-(6-(3-(4-chlorophenyl)propoxy)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000013	-	1-[(R)-4-(5-hexyloxy-1-methylindol-3-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000016	-	1-[(R)-1-hydroxy-4-(6-(4-phenylbutyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000017	-	1-[(R)-1-hydroxy-4-(6-(3-(3-pyridyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000017	-	1-[(R)-1-hydroxy-4-(6-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000024	-	1-[(R)-4-(6-hexanoylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000026	-	1-[(R)-1-hydroxy-4-(1-methyl-5-(3-phenylpropoxy)indol-3-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.00003	-	1-[(R)-1-hydroxy-4-(6-(3-phenylpropionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000034	-	1-[(R)-1-hydroxy-4-(6-(4-(4-methylphenyl)butyrylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000038	-	1-[(R)-1-hydroxy-4-(6-(3-(4-methylphenyl)propionylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000055	-	1-[(R)-4-(6-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000057	-	1-[(R)-1-hydroxy-4-(6-(3-(4-methoxyphenyl)propionylamino)indol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.000091	-	1-[(R)-1-hydroxy-4-(6-(6-phenylhexanoylamino)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.00024	-	1-[(R)-4-(6-butoxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.0013	-	1-[(R)-4-(6-acetylaminoindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.0019	-	1-[(R)-1-hydroxy-4-(5-(3-phenylpropoxy)indol-1-yl)-2-butyl]imidazole-4-carboxamide	-	Bos taurus
0.0062	-	1-[(R)-4-(5-hexyloxyindol-1-yl)-1-hydroxy-2-butyl]imidazole-4-carboxamide	-	Bos taurus