Literature summary for 3.4.24.B4 extracted from

Schnute, M.E.; OBrien, P.M.; Nahra, J.; Morris, M.; Howard Roark, W.; Hanau, C.E.; Ruminski, P.G.; Scholten, J.A.; Fletcher, T.R.; Hamper, B.C.; Carroll, J.N.; Patt, W.C.; Shieh, H.S.; Collins, B.; Pavlovsky, A.G.; Palmquist, K.E.; Aston, K.W.; Hitchcock, J.; Rogers, M.D.; McDonald, J.; Johnson, A.R.; Munie, G.E.
Discovery of (pyridin-4-yl)-2H-tetrazole as a novel scaffold to identify highly selective matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis (2010), Bioorg. Med. Chem. Lett., 20, 576-580.

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Inhibitors

Inhibitors	Comment	Organism
4-([5-[2-(benzylcarbamoyl)-6-methylpyridin-4-yl]-2H-tetrazol-2-yl]methyl)benzoic acid	-	Homo sapiens
4-([5-[2-(benzylcarbamoyl)-6-methylpyridin-4-yl]-2H-tetrazol-2-yl]methyl)cyclohexanecarboxylic acid	-	Homo sapiens
4-([6-[(4-methoxybenzyl)carbamoyl]-4-oxopyrido[3,4-d]pyrimidin-3(4H)-yl]methyl)benzoic acid	-	Homo sapiens
4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3-chloro-4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3-chlorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3-cyanobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3-fluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3-hydroxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(3-methoxybenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(4-chlorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(4-fluoro-3-hydroxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(4-fluoro-3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(4-fluoro-3-methylbenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(4-fluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(4-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[(5-[2-[(4-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[(5-[2-[(4-methoxybenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	-	Homo sapiens
4-[([3-[(3-methoxybenzyl)carbamoyl]benzoyl]amino)methyl]benzoic acid	-	Homo sapiens
4-[([3-[2-(3-methoxybenzyl)-2H-tetrazol-5-yl]benzoyl]amino)methyl]benzoic acid	-	Homo sapiens
4-[([3-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]benzoyl]amino)methyl]benzoic acid	-	Homo sapiens
4-[[1-methyl-2,4-dioxo-6-(3-phenylprop-1-yn-1-yl)-1,4-dihydroquinazolin-3(2H)-yl]methyl]benzoic acid	-	Homo sapiens
4-[[5-(2-methyl-6-[[3-(propan-2-yloxy)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]cyclohexanecarboxylic acid	-	Homo sapiens
4-[[5-(2-methyl-6-[[3-(trifluoromethyl)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]benzoic acid	-	Homo sapiens
4-[[5-(2-[[3-(trifluoromethyl)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]benzoic acid	-	Homo sapiens
4-[[5-(2-[[4-fluoro-3-(trifluoromethyl)benzyl]carbamoyl]-6-methylpyridin-4-yl)-2H-tetrazol-2-yl]methyl]cyclohexanecarboxylic acid	-	Homo sapiens
additional information	discovery of (pyridin-4-yl)-2H-tetrazole as a scaffold to identify highly selective MMP-13 inhibitors for the treatment of osteoarthritis	Homo sapiens
N,N'-bis(3-methoxybenzyl)benzene-1,3-dicarboxamide	-	Homo sapiens
N,N'-bis(pyridin-3-ylmethyl)pyrimidine-4,6-dicarboxamide	-	Homo sapiens

Metals/Ions

Metals/Ions	Comment	Organism	Structure
Zn2+	dependent on	Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
type II collagen + H2O	Homo sapiens	-	?	-	?

Organism

Organism	UniProt	Comment	Textmining
Homo sapiens	P45452	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
cartilage	articular, and osteoarthritic	Homo sapiens	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
type II collagen + H2O	-	Homo sapiens	?	-	?

Synonyms

Synonyms	Comment	Organism
MMP-13	-	Homo sapiens

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism
0.00000016	-	4-[(5-[2-[(3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.00000018	-	4-[(5-[2-[(3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.00000022	-	4-[(5-[2-[(4-fluoro-3-methylbenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.00000026	-	4-[(5-[2-[(3-chloro-4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000003	-	4-[(5-[2-[(4-fluoro-3-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.00000062	-	4-[[5-(2-[[4-fluoro-3-(trifluoromethyl)benzyl]carbamoyl]-6-methylpyridin-4-yl)-2H-tetrazol-2-yl]methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000014	-	4-[(5-[2-[(4-fluoro-3-hydroxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000015	-	4-[(5-[2-[(3-hydroxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000015	-	4-[[5-(2-methyl-6-[[3-(propan-2-yloxy)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000021	-	4-[(5-[2-[(3-methoxybenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000025	-	4-[[5-(2-methyl-6-[[3-(trifluoromethyl)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000036	-	4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000042	-	4-[(5-[2-[(4-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000044	-	4-[(5-[2-[(4-methoxybenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000044	-	4-[(5-[2-[(4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000053	-	4-[(5-[2-[(4-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000067	-	4-[(5-[2-[(3-cyanobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000075	-	4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000165	-	4-[[5-(2-[[3-(trifluoromethyl)benzyl]carbamoyl]pyridin-4-yl)-2H-tetrazol-2-yl]methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000181	-	4-[(5-[2-[(3-chlorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000221	-	4-[(5-[2-[(3-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000223	-	4-([5-[2-(benzylcarbamoyl)-6-methylpyridin-4-yl]-2H-tetrazol-2-yl]methyl)benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000286	-	4-[(5-[2-[(3-fluorobenzyl)carbamoyl]-6-methylpyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000313	-	4-([5-[2-(benzylcarbamoyl)-6-methylpyridin-4-yl]-2H-tetrazol-2-yl]methyl)cyclohexanecarboxylic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000367	-	4-[(5-[2-[(4-methoxybenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000434	-	4-[(5-[2-[(3,4-difluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000653	-	4-[(5-[2-[(4-fluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.0000759	-	4-[(5-[2-[(3-fluorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens
0.000227	-	4-[(5-[2-[(4-chlorobenzyl)carbamoyl]pyridin-4-yl]-2H-tetrazol-2-yl)methyl]benzoic acid	pH not specified in the publication, temperature not specified in the publication	Homo sapiens

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
0.00000067	-	pH not specified in the publication, temperature not specified in the publication	Homo sapiens	4-[[1-methyl-2,4-dioxo-6-(3-phenylprop-1-yn-1-yl)-1,4-dihydroquinazolin-3(2H)-yl]methyl]benzoic acid
0.00013	-	pH not specified in the publication, temperature not specified in the publication	Homo sapiens	4-[([3-[2-(4-methoxybenzyl)-2H-tetrazol-5-yl]benzoyl]amino)methyl]benzoic acid
0.00053	-	pH not specified in the publication, temperature not specified in the publication	Homo sapiens	4-[([3-[2-(3-methoxybenzyl)-2H-tetrazol-5-yl]benzoyl]amino)methyl]benzoic acid
0.0017	-	pH not specified in the publication, temperature not specified in the publication	Homo sapiens	4-[([3-[(3-methoxybenzyl)carbamoyl]benzoyl]amino)methyl]benzoic acid

General Information

General Information	Comment	Organism
additional information	osteoarthritis, involving MMP-13, is a degenerative joint disease characterized by the erosion of articular cartilage leading to pain and reduced mobility	Homo sapiens