Information on EC 3.4.24.B12 - ADAMTS5 endopeptidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.4.24.B12
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
ADAMTS5 endopeptidase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
proteolytic degradation of proteins
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis
-
endoproteolytic cleavage of specific Glu-Xaa bonds within the core protein of aggrecan
hydrolysis of peptide bond
CAS REGISTRY NUMBER
COMMENTARY hide
405150-12-1
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
Abz-TEGEARGSVI-Dap(2,4-dinitrophenyl)-KK + H2O
?
show the reaction diagram
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-
-
-
?
aggrecan + H2O
2 aggrecan fragment
show the reaction diagram
aggrecan + H2O
7 aggregan fragment
show the reaction diagram
several cleavage sites are determined
product determination, overview
?
aggrecan + H2O
?
show the reaction diagram
aggrecan + H2O
fragment 74ALGS + ?
show the reaction diagram
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-
-
-
?
aggrecan-interglobular domain + H2O
?
show the reaction diagram
alpha2-macroglobulin + H2O
?
show the reaction diagram
-
-
-
-
?
biglycan + H2O
?
show the reaction diagram
-
-
-
-
?
brevican +
?
show the reaction diagram
-
-
-
-
?
brevican + H2O
?
show the reaction diagram
brevican + H2O + H2O
?
show the reaction diagram
-
-
-
-
?
C6-(Gly-Pro-Hyp-Pro-Hyp-Gly)2-Gly-Pro-Hyp-Gly-Thr-Lys(Mca)-Gly-Glu-Leu-Glu-Gly-Arg-Gly-Thr-Lys(Dnp)-Gly-Ile-Ser-(Gly-Pro-Hyp-Pro-Hyp-Gly)2-Gly-Pro-Hyp-NH2 + H2O
?
show the reaction diagram
-
-
-
-
?
carboxymethylated transferrin + H2O
?
show the reaction diagram
-
-
-
-
?
casein + H2O
?
show the reaction diagram
-
-
-
-
?
decorin + H2O
?
show the reaction diagram
-
-
-
-
?
FAM-AELQGRPISIAK-TAMRA + H2O
?
show the reaction diagram
-
activity measured using a quenched fluorescent substrate
-
-
?
fibromodulin + H2O
29000 Da fibromodulin fragment + ?
show the reaction diagram
-
very low activity
-
-
?
fibromodulin + H2O
?
show the reaction diagram
-
-
-
-
?
Fibronectin + H2O
?
show the reaction diagram
-
-
-
-
?
Gelatin + H2O
?
show the reaction diagram
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weak activity
-
-
?
K(6FAM)-DVQEFRGVTAVIRC(Qsy9)-KGK + H2O
K-(6FAM)-DVQE + FRGVTAVIRC(Qsy9)-KGK
show the reaction diagram
-
-
-
-
?
K-[6FAM]-DVQEFRGVTAVIRC-[Qsy9]-KGK + H2O
K-[6FAM]-DVQE + FRGVTAVIRC-[Qsy9]-KGK
show the reaction diagram
-
-
-
-
?
Lys(7-methoxycoumarin-4-yl)-Lys-Gln-Glu-Phe-Arg-Gly-Gln-Thr-Lys(Dnp)-NH2 + H2O
?
show the reaction diagram
-
-
-
-
?
Lys(carboxyfluorescein)-Asp-Val-Gln-Glu-Phe-Arg-Gly-Val-Thr-Ala-Val-Ile-Arg-Lys(tetramethylrhodamine)-Lys-Gly-Lys-NH2 + H2O
?
show the reaction diagram
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-
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?
matrilin-2 + H2O
?
show the reaction diagram
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substrate contains two putative cleavage sites. The first site is located between residues D851 and L852 in the middle of the domain and the second at the boundary with the coiled-coil domain at the C-terminus. Deletion of the entire unique domain eliminates the proteolysis of matrilin-2. The first cleavage site is present in all matrilin-2 oligomers, the second cleavage site becomes apparent only in the matrilin-2 hetero-oligomers with matrilin-1 or matrilin-3
-
?
matrilin-4 + H2O
?
show the reaction diagram
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matrilin-4 is specifically cleaved by ADAMTS-5
-
-
?
o-aminobenzoyl-Thr-Glu-Ser-Glu-Ser-Arg-Gly-Ala-Ile-Tyr-(N-3-[2,4-dinitrophenyl]-L-2,3-diaminopropionyl)-Lys-Lys-NH2 + H2O
o-aminobenzoyl-Thr-Glu-Ser-Glu + Ser-Arg-Gly-Ala-Ile-Tyr-(N-3-[2,4-dinitrophenyl]-L-2,3-diaminopropionyl)-Lys-Lys-NH2
show the reaction diagram
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recombinant ADAMTS-5 cleaves this substrate more readily than ADAMTS-4 in vitro
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-
?
proteins + H2O
peptides
show the reaction diagram
versican + H2O
?
show the reaction diagram
versican + H2O + H2O
fragment DPEAAE441 + ?
show the reaction diagram
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-
-
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?
VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG + H2O
?
show the reaction diagram
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43mer peptide substrate
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-
?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
aggrecan + H2O
2 aggrecan fragment
show the reaction diagram
-
cleavage site is Glu373-Ala374, reaction is relevant to cartilage degeneration in inflammatory joint diseases
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?
aggrecan + H2O
?
show the reaction diagram
proteins + H2O
peptides
show the reaction diagram
versican + H2O
?
show the reaction diagram
Q9R001
expression of Adamts5 during neuromuscular development and in smooth muscle cells coincides with the broadly distributed proteoglycan versican, an ADAMTS5 substrate
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?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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metalloproteinase
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2R,3S)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2,3-dimethylcyclopropanecarboxylate
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(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylic acid
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-
(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[5-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-([[4'-(acetylamino)biphenyl-4-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-([[4'-(dimethylamino)biphenyl-4-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
-
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(1R,2S)-1-([[4-(4-chlorophenyl)-3,6-dihydropyridin-1(2H)-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
-
-
(1R,2S)-1-([[6-(4-chlorophenyl)pyridin-3-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
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-
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-2-ylethyl)amino]-2-phenylcyclopropanecarboxylic acid
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-
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-3-ylethyl)amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-4-ylethyl)amino]-2-phenylcyclopropanecarboxylic acid
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-
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl]amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-1,2,3-triazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-1,2,4-triazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-imidazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-tetrazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2,5-dioxopyrrolidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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-
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxo-1,3-oxazinan-3-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxopiperidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2H-1,2,3-triazol-2-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(3-methoxy-2-oxopyridin-1(2H)-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(4H-1,2,4-triazol-4-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(7H-purin-7-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(9H-purin-9-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
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(1S)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2,2-dimethylcyclopropanecarboxylate
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0.001 mM, 19.6% inhibition
(1S,2R)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylate
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0.0003 mM, 18% inhibition
(1S,2R)-1-([[5-(2-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
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0.001 mM, 48% inhibition
(1S,2R)-1-([[5-(3-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-(propan-2-yl)cyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-cyclohexylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-methyl-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-([[5-(5-chloropyridin-2-yl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
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(1S,2R)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl]amino]-2-phenylcyclopropanecarboxylate
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(1S,2R,3R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
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(1S,2R,3R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
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(1S,2S)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-methylcyclopropanecarboxylate
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0.001 mM, 3.5% inhibition
(1S,2S)-2-benzyl-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)cyclopropanecarboxylate
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0.001 mM, 25% inhibition
(1S,2S,3R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
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(2R)-2-[4-(1,3-benzodioxol-5-yl)benzyl]-N4-hydroxy-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
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nanomolar inhibitor of both ADAMTS-5
(2R)-N4-hydroxy-2-(3-hydroxybenzyl)-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
(2R,5R)-1-([4-[(2,4-dichlorobenzyl)oxy]phenyl]sulfonyl)-N,5-dihydroxy-3,3-dimethylpiperidine-2-carboxamide
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(2S,3R)-2-[(cyclopropylmethyl)amino]-N1-hydroxy-N4-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-3-methylbutanediamide
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the reduced pattern of H-bond interactions is suitable for the flexible environment of ADAMTS4 and ADAMTS5 since it enables the inhibitor to re-optimize its interaction pattern step-by-step, following the loop motion. The conformational flexibility observed for the S1' loop of ADAMTS4 and ADAMTS5 seems to be correlated to the motion of the TS-domain
(3R)-N2-(cyclopropylmethyl)-N1-hydroxy-3-(3-hydroxybenzyl)-N4-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-L-aspartamide
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(5E)-2-thioxo-5-([3-[3-(trifluoromethyl)phenoxy]phenyl]methylidene)-1,3-thiazolidin-4-one
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(5E)-3-benzyl-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-([3-methoxy-4-[(4-methoxybenzyl)oxy]phenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-([4-[(4-chlorobenzyl)oxy]-3-methoxyphenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[(3-phenoxyphenyl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-ethyl-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3,5-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(4-methoxyphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(4-methylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[3-(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5E)-5-[[4-(benzyloxy)-3-methoxyphenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5Z)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5Z)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
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(5Z)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-1-methyl-2-thioxoimidazolidin-4-one
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(5Z)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
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(5Z)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
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(5Z)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
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(E)-2-((1H-benzo[d]imidazol-2-yl)methylene)-5-propylthiazolidin-4-one
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; potent small-molecule ADAMTS-5 inhibitor with good permeability
(E)-4-[2-(3,5-dihydroxyphenyl)ethenyl]1,2-benzenediol
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i.e. piceatannol
(R)-2-(4'-((4-(4-fluorobenzoyl)phenoxy)methyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid
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(R)-2-(4'-((4-(cyclohexanecarbonyl)phenoxy)methyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid
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(R)-2-(4'-((4-isobutyrylphenoxy)methyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid
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(R)-3-methyl-2-(4'-((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)biphenyl-4-ylsulfonamido)butanoic acid
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(S)-2-dimethylamino-N-hydroxy-3,3-dimethyl-4-[(4-phenoxyphenyl)-sulfonyl]-butanamide
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SC81956, potent inhibitor of ADAMTS-5
1-benzyl-4-((4-(4-chlorophenoxy) phenyl)-sulfonyl)-N-hydroxypiperidine-4-carboxamide
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multi-MMP inhibitor
2-(4-acetylphenoxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]acetamide
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2-(benzyloxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]acetamide
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2-(benzyloxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]acetamide
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2-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
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2-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
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2-[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
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2-[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
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2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]acetamide
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2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]acetamide
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2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]acetamide
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2-[4-(benzyloxy)phenyl]-2,3-dihydro-1-oxo-1H-pyrrolo[3,4-c]quinoline-4-carboxylate
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the inhibitor is unable to discriminate between ADAMTS-5 and ADAMTS-4
2-[4-(benzyloxy)phenyl]-2,3-dihydro-N-hydroxy-1-oxo-1Hpyrrolo[3,4-c]quinoline-4-carboxamide
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2-[4-(benzyloxy)phenyl]-3-oxoisoindoline-4-carboxylic acid
-
does not inhibit ADAMTS-4
2-[4-(benzyloxy)phenyl]-N-hydroxy-3-oxoisoindoline-4-carboxamide
-
does not inhibit ADAMTS-4
3-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanoic acid
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3-[2-[(Z)-(4-oxo-1,3-thiazolidin-2-ylidene)methyl]-4-(pyridin-2-yl)-1,3-thiazol-5-yl]propanoic acid
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inhibits the spontaneous aggrecan degradation in IL-1-stimulated bovine cartilage, shows good selectivity over other metalloproteases; inhibits the spontaneous aggrecan degradation in IL-1-stimulated bovine cartilage, shows good selectivity over other metalloproteases
4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-phenyl-5-(2-pyrimidin-1(6H)-ylpiperazin-1-yl)-1H-pyrazole-1-carbonitrile
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-
4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-5-(2-pyrimidin-1(6H)-ylpiperazin-1-yl)-3-(trifluoromethyl)-1H-pyrazole-1-carbonitrile
-
-
5-([1,3-diphenyl-5-[(thiophen-2-ylmethyl)sulfanyl]-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([1-methyl-5-[(2H-thiopyran-2-ylmethyl)sulfanyl]-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
40% inhibition at 0.02 mM
5-([1-methyl-5-[(4-methylphenyl)sulfanyl]-3-phenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([1-phenyl-5-[2-(tetrahydrothiophen-2-yl)ethoxy]-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(2-chlorobenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(4-chlorobenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(4-chlorobenzyl)sulfanyl]-1-phenyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(4-chlorophenyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
47% inhibition at 0.02 mM
5-([5-[(4-methoxybenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
53% inhibition at 0.02 mM
5-([5-[(4-tert-butylbenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(furan-2-ylmethyl)sulfanyl]-1,3-diphenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(furan-2-ylmethyl)sulfanyl]-1-methyl-3-phenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[(furan-2-ylmethyl)sulfanyl]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
42% inhibition at 0.02 mM
5-([5-[2-(4-chlorophenyl)ethoxy]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[2-(4-fluorophenyl)ethoxy]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[2-(4-methoxyphenyl)ethoxy]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
31% inhibition at 0.02 mM
5-([5-[4-(4-chlorophenyl)piperazin-1-yl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-([5-[4-(4-chlorophenyl)piperazin-1-yl]-1-phenyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
-
-
5-[(4-chlorobenzyl)sulfanyl]-4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-(2,2,2-trifluoroethyl)-1H-pyrazole-1-carbonitrile
-
-
5-[(furan-2-ylmethyl)sulfanyl]-4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-phenyl-1H-pyrazole-1-carbonitrile
-
-
5-[[1-methyl-5-(phenylsulfanyl)-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methylen]-2-thioxo-1,3-thiazolidin-4-one
-
28% inhibition at 0.02 mM
5-[[5-(4-methylpiperazin-1-yl)-1,3-diphenyl-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
-
-
5-[[5-(4-methylpiperazin-1-yl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
-
45% inhibition at 0.02 mM
5-[[5-(benzylsulfanyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
-
44% inhibition at 0.02 mM
5-[[5-(benzylsulfanyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
-
-
aggrecanase inhibitor BB-16
-
prevents aggrecan degradation in osteoarthritic cartilage
alpha2-Macroglobulin
-
batimastat
-
-
BB-16
-
(2S,5R,6S)-3-Aza-4-oxo-10-oxa-5-hexyl-2-(methylcarboxamido)-10-paracyclophane-6-N-hydroxycarboxamide
calcium pentosan polysulfate
-
chemically sulfated xylopyranose from beechwood. Multifaceted exosite inhibitor, protects cartilage against aggrecan degradation. Inhibitor interacts with the noncatalytic spacer domain of isoform ADAMTS-4 and the cysteine-rich domain of ADAMTS-5, blocking activity against their natural substrate aggrecan with inhibitory concentration 50 values of 10-40 nM but only weakly inhibiting hydrolysis of a nonglycosylated recombinant protein substrate. calcium pentosan polysulfate increases cartilage levels of tissue inhibitor of metalloproteinases TIMP-3, an endogenous inhibitor of ADAMTS-4 and -5
-
catechin gallate esters
-
from green tea Camellia sinensis, strong inhibition, independent of Zn2+, reversible
-
doxycycline
-
dose-dependently inhibits the activity of rhADAMTS4 in vitro
heparin
Interleukin-1beta
lower mRNA level of aggrecan
-
marimastat
-
-
minocycline
-
dose-dependently inhibits the activity of rhADAMTS4 in vitro
N-benzyl-N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-D-phenylalanine
-
30% inhibition at 0.01 mM
N-hydroxy-4-(4-(4-(trifluoromethyl)-phenoxy)phenylsulfonyl)-tetrahydro-2H-pyran-4-carboxamide
-
nanomolar inhibitor of both ADAMTS-5
N-hydroxy-4-([4-[4-(trifluoromethyl)phenoxy]phenyl]sulfonyl)tetrahydro-2H-pyran-4-carboxamide
-
-
N-terminal domain of tissue inhibitor of metalloproteinases-3
-
all isoforms of ADAMTS-5 are effectively inhibited. Inhibited more strongly by N-terminal domain of tissue inhibitor of metalloproteinases-3 than by full-length tissue inhibitor of metalloproteinases-3
-
N-terminal inhibitory domain of tissue inhibitor of metalloproteinases 3
-
N-terminal mutants of N-TIMP-3 (tissue inhibitor of metalloproteinases 3) that have lost their matrix metalloproteinaseP-inhibitory activities (N-TIMP-3(T2G) and [-1A]N-TIMP-3), retain their ability to inhibit ADAMTS-4 and ADAMTS-5. The [-2A]N-TIMP-3 mutant also retains strong affinity with ADAMTS-5, but has a lower affinity for ADAMTS-4 and ADAM17
-
N-[(1R)-1-(dihydroxymethyl)-2-methylpropyl]-4'-{[4-(2-methylpropanoyl)phenoxy]methyl}biphenyl-4-sulfonamide
-
-
N-[(2-chlorophenyl)(8-hydroxy-5-methylquinolin-7-yl)methyl]-2-phenoxyacetamide
-
-
N-[(2-chlorophenyl)(8-hydroxy-5-nitroquinolin-7-yl)methyl]-2-phenoxyacetamide
-
-
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-D-phenylalanine
-
-
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-N-(cyclohexylmethyl)-D-phenylalanine
-
22% inhibition at 0.01 mM
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-N-(cyclopropylmethyl)-D-phenylalanine
-
46% inhibition at 0.01 mM
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-N-methyl-D-phenylalanine
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-bromo-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-methyl-N2-phenylglycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-cyanophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-fluorophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-methylphenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-nitrophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-methyl-N2-phenylglycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-(pyridin-3-yloxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-methyl-N2-phenylglycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-chlorophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(4-methoxyphenoxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(4-methylphenoxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(pyridin-3-yloxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-(4-cyanophenyl)glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-methyl-N2-phenylglycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-[3-(dimethylamino)phenyl]glycinamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-(4-chlorophenoxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-(4-methylphenoxy)acetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
-
-
N-[(5-chloro-8-hydroxyquinolin-7-yl)[2-(trifluoromethyl)phenyl]methyl]-2-phenoxyacetamide
-
-
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
-
-
N-[(8-hydroxy-5-methylquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
-
-
N-[(8-hydroxy-5-nitroquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
-
-
N-[(8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
-
-
N-[[(4S)-4-(1-methylimidazol-2-yl)-2,5-dioxo-imidazolidin-4-yl]methyl]-5-(trifluoromethyl)benzofuran-2-carboxamide
-
inhibitor has excellent selectivity over other zinc metalloproteases such as TACE, MMP2, MMP3, MMP13, and MMP14
N2-(4-acetylphenyl)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]glycinamide
-
-
N2-(4-acetylphenyl)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]glycinamide
-
-
N2-(biphenyl-4-ylcarbonyl)-N-(2-phenylpropan-2-yl)-L-alpha-glutamine
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-methylglycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]glycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-methylglycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]glycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-methylglycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-methylglycinamide
-
-
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]glycinamide
-
-
N2-[4-(acetylamino)phenyl]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]glycinamide
-
-
NaCl
-
the activity is very low at or below 50 mM NaCl or above 500 mM NaCl
pyrogallol
-
-
tetracycline
-
dose-dependently inhibits the activity of rhADAMTS4 in vitro
TIMP-3
-
tissue inhibitor of matrix metalloproteinases-3
-
TIMP-3
-
tissue inhibitor of metalloproteinases-3
-
[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl](phenyl)acetic acid
-
-
[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
-
-
[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl](phenyl)acetic acid
-
-
[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
interleukin-1alpha
-
Interleukin-1beta
-
increased transcription in the presence of interleukin-1beta
-
oncostatin M
-
increased transcription in the presence of interleukin-1alpha
-
retinoate
-
increased transcription in the presence of retinoate
retinoic acid
-
tissue necrosis factor alpha
-
increased transcription in the presence of tissue necrosis factor alpha
-
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000093
(2R)-N4-hydroxy-2-(3-hydroxybenzyl)-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
-
or above, pH not specified in the publication, temperature not specified in the publication
0.000017
(2S,3R)-2-[(cyclopropylmethyl)amino]-N1-hydroxy-N4-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-3-methylbutanediamide
-
or above, pH not specified in the publication, temperature not specified in the publication
0.0012 - 0.0111
(E)-4-[2-(3,5-dihydroxyphenyl)ethenyl]1,2-benzenediol
0.000106
marimastat
-
pH not specified in the publication, temperature not specified in the publication
0.00013 - 0.00101
N-terminal domain of tissue inhibitor of metalloproteinases-3
-
0.00363 - 0.037
pyrogallol
0.00000066
TIMP-3
-
pH 7.5, 37C
-
0.00063 - 0.00117
tissue inhibitor of metalloproteinases-3
-
additional information
additional information
-
Ki(app) of N-terminal alanine-extension mutants and of position [-1] mutants of N-terminal inhibitory domain of tissue inhibitor of metalloproteinases 3
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0008
(1R,2R,3S)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2,3-dimethylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000073
(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00007
(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0002
(1R,2S)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[5-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0045
(1R,2S)-1-([[4'-(acetylamino)biphenyl-4-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0066
(1R,2S)-1-([[4'-(dimethylamino)biphenyl-4-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00088
(1R,2S)-1-([[4-(4-chlorophenyl)-3,6-dihydropyridin-1(2H)-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0011
(1R,2S)-1-([[6-(4-chlorophenyl)pyridin-3-yl]sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino)-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00082
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-2-ylethyl)amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00029
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-3-ylethyl)amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
-
0.00075
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl](2-pyridin-4-ylethyl)amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00027
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-1,2,3-triazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
-
0.00018
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-1,2,4-triazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0002
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-imidazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00027
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(1H-tetrazol-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0001
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2,5-dioxopyrrolidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00018
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxo-1,3-oxazinan-3-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
-
0.00022
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00021
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxopiperidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.0002
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2-oxopyrrolidin-1-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00026
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(2H-1,2,3-triazol-2-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
-
0.00078
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(3-methoxy-2-oxopyridin-1(2H)-yl)ethyl]amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
-
0.00019
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(4H-1,2,4-triazol-4-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.000071
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(7H-purin-7-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00017
(1R,2S)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl][2-(9H-purin-9-yl)ethyl]amino]-2-phenylcyclopropanecarboxylic acid
Homo sapiens
-
-
0.00021
(1S,2R)-1-([(4'-chlorobiphenyl-4-yl)sulfonyl][2-[4-(methoxycarbonyl)-1H-imidazol-1-yl]ethyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000094
(1S,2R)-1-([[5-(3-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00077
(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-(propan-2-yl)cyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00036
(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-cyclohexylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000032
(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-methyl-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00008
(1S,2R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00001
(1S,2R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00006
(1S,2R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.0001
(1S,2R)-1-([[5-(5-chloropyridin-2-yl)thiophen-2-yl]sulfonyl]amino)-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000084
(1S,2R)-1-[[(4'-chlorobiphenyl-4-yl)sulfonyl]amino]-2-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.0000074
(1S,2R,3R)-1-([[5-(4-chloro-1H-pyrazol-1-yl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000021
(1S,2R,3R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.00012
(1S,2S,3R)-1-([[5-(4-chlorophenyl)thiophen-2-yl]sulfonyl]amino)-2-methyl-3-phenylcyclopropanecarboxylate
Homo sapiens
-
pH and temperature not specified in the publication
0.000129
(2R)-2-[4-(1,3-benzodioxol-5-yl)benzyl]-N4-hydroxy-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
Homo sapiens
-
pH and temperature not specified in the publication
0.000093
(2R)-N4-hydroxy-2-(3-hydroxybenzyl)-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
Homo sapiens
-
pH 7.5, 37C
0.0000014
(2R,5R)-1-([4-[(2,4-dichlorobenzyl)oxy]phenyl]sulfonyl)-N,5-dihydroxy-3,3-dimethylpiperidine-2-carboxamide
Homo sapiens
-
37C, pH and temperature not specified in the publication
0.000017
(3R)-N2-(cyclopropylmethyl)-N1-hydroxy-3-(3-hydroxybenzyl)-N4-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-L-aspartamide
Homo sapiens
-
pH 7.5, 37C
0.0053
(5E)-2-thioxo-5-([3-[3-(trifluoromethyl)phenoxy]phenyl]methylidene)-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.067
(5E)-3-benzyl-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.0116
(5E)-5-([3-methoxy-4-[(4-methoxybenzyl)oxy]phenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0035
(5E)-5-([4-[(4-chlorobenzyl)oxy]-3-methoxyphenyl]methylidene)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.022
(5E)-5-[(3-phenoxyphenyl)methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.022 mM
0.0018
(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.067
(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-(2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.067
(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-ethyl-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.067
(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-methyl-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.067
(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-3-phenyl-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.0014
(5E)-5-[[3,5-bis(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0032
(5E)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0025
(5E)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0049 - 0.022
(5E)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
0.0162
(5E)-5-[[3-(4-methoxyphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0148
(5E)-5-[[3-(4-methylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0017
(5E)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0201
(5E)-5-[[3-(benzyloxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.022
(5E)-5-[[4-(benzyloxy)-3-methoxyphenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
IC50 above 0.022 mM
0.01
(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0092
(5Z)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.067
(5Z)-5-[[3-(3,5-dichlorophenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.022
(5Z)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-1-methyl-2-thioxoimidazolidin-4-one
Homo sapiens
-
IC50 above 0.022 mM
0.067
(5Z)-5-[[3-(4-chlorophenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.0068
(5Z)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.067
(5Z)-5-[[3-(4-tert-butylphenoxy)phenyl]methylidene]-2-thioxoimidazolidin-4-one
Homo sapiens
-
IC50 above 0.067 mM
0.00017 - 0.021
(E)-2-((1H-benzo[d]imidazol-2-yl)methylene)-5-propylthiazolidin-4-one
0.0026
(R)-2-(4'-((4-(cyclohexanecarbonyl)phenoxy)methyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid
Mus musculus
-
-
0.0084
(R)-2-(4'-((4-isobutyrylphenoxy)methyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid
Mus musculus
-
-
0.0066
(R)-3-methyl-2-(4'-((5-oxo-5,6,7,8-tetrahydronaphthalen-2-yloxy)methyl)biphenyl-4-ylsulfonamido)butanoic acid
Mus musculus
-
-
0.00042
1-benzyl-4-((4-(4-chlorophenoxy) phenyl)-sulfonyl)-N-hydroxypiperidine-4-carboxamide
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.00233
2-(4-acetylphenoxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]acetamide
Homo sapiens
-
-
0.00083
2-(benzyloxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]acetamide
Homo sapiens
-
-
0.0007
2-(benzyloxy)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]acetamide
Homo sapiens
-
-
0.0011
2-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
Homo sapiens
-
-
0.0013
2-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
Homo sapiens
-
-
0.0018
2-[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-methylbutanoic acid
Homo sapiens
-
-
0.0016
2-[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
Homo sapiens
-
-
0.00234
2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]acetamide
Homo sapiens
-
-
0.00133
2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]acetamide
Homo sapiens
-
-
0.00339
2-[4-(acetylamino)phenoxy]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]acetamide
Homo sapiens
-
-
0.012
2-[4-(benzyloxy)phenyl]-2,3-dihydro-1-oxo-1H-pyrrolo[3,4-c]quinoline-4-carboxylate
Homo sapiens
-
37C, pH and temperature not specified in the publication
0.00095
2-[4-(benzyloxy)phenyl]-2,3-dihydro-N-hydroxy-1-oxo-1Hpyrrolo[3,4-c]quinoline-4-carboxamide
Homo sapiens
-
37C, pH and temperature not specified in the publication
0.0053
3-[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]propanoic acid
Homo sapiens
-
-
0.00023 - 0.023
3-[2-[(Z)-(4-oxo-1,3-thiazolidin-2-ylidene)methyl]-4-(pyridin-2-yl)-1,3-thiazol-5-yl]propanoic acid
0.008
4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-phenyl-5-(2-pyrimidin-1(6H)-ylpiperazin-1-yl)-1H-pyrazole-1-carbonitrile
Homo sapiens
-
-
0.0117
4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-5-(2-pyrimidin-1(6H)-ylpiperazin-1-yl)-3-(trifluoromethyl)-1H-pyrazole-1-carbonitrile
Homo sapiens
-
-
0.0037
5-([1,3-diphenyl-5-[(thiophen-2-ylmethyl)sulfanyl]-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0083
5-([1-methyl-5-[(4-methylphenyl)sulfanyl]-3-phenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0091
5-([1-phenyl-5-[2-(tetrahydrothiophen-2-yl)ethoxy]-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0232
5-([5-[(2-chlorobenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0011
5-([5-[(4-chlorobenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0025
5-([5-[(4-chlorobenzyl)sulfanyl]-1-phenyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0022
5-([5-[(4-tert-butylbenzyl)sulfanyl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0067
5-([5-[(furan-2-ylmethyl)sulfanyl]-1,3-diphenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0141
5-([5-[(furan-2-ylmethyl)sulfanyl]-1-methyl-3-phenyl-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0042
5-([5-[2-(4-chlorophenyl)ethoxy]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0071
5-([5-[2-(4-fluorophenyl)ethoxy]-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.009
5-([5-[4-(4-chlorophenyl)piperazin-1-yl]-1-methyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0021
5-([5-[4-(4-chlorophenyl)piperazin-1-yl]-1-phenyl-3-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl]methyl)-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0042
5-[(4-chlorobenzyl)sulfanyl]-4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-(2,2,2-trifluoroethyl)-1H-pyrazole-1-carbonitrile
Homo sapiens
-
-
0.0046
5-[(furan-2-ylmethyl)sulfanyl]-4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-yl)methyl]-3-phenyl-1H-pyrazole-1-carbonitrile
Homo sapiens
-
-
0.0046
5-[[5-(4-methylpiperazin-1-yl)-1,3-diphenyl-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0169
5-[[5-(benzylsulfanyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]-2-thioxo-1,3-thiazolidin-4-one
Homo sapiens
-
-
0.0707
doxycycline
Homo sapiens
-
pH and temperature not specified in the publication
0.000106
marimastat
Homo sapiens
-
pH 7.5, 37C
0.111
minocycline
Homo sapiens
-
pH and temperature not specified in the publication
0.129
N-hydroxy-4-(4-(4-(trifluoromethyl)-phenoxy)phenylsulfonyl)-tetrahydro-2H-pyran-4-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00029
N-hydroxy-4-([4-[4-(trifluoromethyl)phenoxy]phenyl]sulfonyl)tetrahydro-2H-pyran-4-carboxamide
Homo sapiens
-
in 100 mM Tris-HCl, 100 mM NaCl, 0.01 mM CaCl2, 0.05% Brij, pH 7.5
0.00242
N-[(2-chlorophenyl)(8-hydroxy-5-methylquinolin-7-yl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00094
N-[(2-chlorophenyl)(8-hydroxy-5-nitroquinolin-7-yl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.002
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-D-phenylalanine
Homo sapiens
-
-
0.008
N-[(4'-chlorobiphenyl-4-yl)sulfonyl]-N-methyl-D-phenylalanine
Homo sapiens
-
-
0.00083
N-[(5-bromo-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00062
N-[(5-bromo-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00035
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
sub-micromol ADAMTS-5 potency and good selectivity over the related metalloproteases ADAMTS-4 (aggrecanase-1), MMP-13, and MMP-12
0.00172
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
Homo sapiens
-
-
0.00148
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
Homo sapiens
-
-
0.00099
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-methyl-N2-phenylglycinamide
Homo sapiens
-
-
0.00232
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-cyanophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00122
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-fluorophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00185
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-methylphenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00121
N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-nitrophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00062
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00337
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
Homo sapiens
-
-
0.00143
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
Homo sapiens
-
-
0.00125
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-methyl-N2-phenylglycinamide
Homo sapiens
-
-
0.00166
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-(pyridin-3-yloxy)acetamide
Homo sapiens
-
-
0.00049
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
sub-micromol ADAMTS-5 potency and good selectivity over the related metalloproteases ADAMTS-4 (aggrecanase-1), MMP-13, and MMP-12
0.00119
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
Homo sapiens
-
-
0.00056
N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-methyl-N2-phenylglycinamide
Homo sapiens
-
sub-micromol ADAMTS-5 potency and good selectivity over the related metalloproteases ADAMTS-4 (aggrecanase-1), MMP-13, and MMP-12. Good balance of potent ADAMTS-5 inhibition, moderate CYP3A4 inhibition and good rat liver microsome stability
0.00083
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-chlorophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00094
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(4-methoxyphenoxy)acetamide
Homo sapiens
-
sub-micromol ADAMTS-5 potency and good selectivity over the related metalloproteases ADAMTS-4 (aggrecanase-1), MMP-13, and MMP-12
0.00077
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(4-methylphenoxy)acetamide
Homo sapiens
-
-
0.00298
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-(pyridin-3-yloxy)acetamide
Homo sapiens
-
-
0.00135
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00167
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methoxyphenyl)methyl]-2-[3-(dimethylamino)phenoxy]acetamide
Homo sapiens
-
-
0.00076
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00158
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-(4-chloro-3-methylphenyl)glycinamide
Homo sapiens
-
-
0.00101
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-(4-cyanophenyl)glycinamide
Homo sapiens
-
-
0.00078
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-methyl-N2-phenylglycinamide
Homo sapiens
-
-
0.00193
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-[3-(dimethylamino)phenyl]glycinamide
Homo sapiens
-
-
0.00046
N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-nitrophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00102
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-(4-chlorophenoxy)acetamide
Homo sapiens
-
-
0.0019
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-(4-methylphenoxy)acetamide
Homo sapiens
-
-
0.00078
N-[(5-chloro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00083
N-[(5-chloro-8-hydroxyquinolin-7-yl)[2-(trifluoromethyl)phenyl]methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00484
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00132
N-[(8-hydroxy-5-methylquinolin-7-yl)(3-nitrophenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00135
N-[(8-hydroxy-5-nitroquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.00228
N-[(8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide
Homo sapiens
-
-
0.000004 - 0.000035
N-[[(4S)-4-(1-methylimidazol-2-yl)-2,5-dioxo-imidazolidin-4-yl]methyl]-5-(trifluoromethyl)benzofuran-2-carboxamide
0.00107
N2-(4-acetylphenyl)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]glycinamide
Homo sapiens
-
-
0.00113
N2-(4-acetylphenyl)-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]glycinamide
Homo sapiens
-
-
0.0011
N2-(biphenyl-4-ylcarbonyl)-N-(2-phenylpropan-2-yl)-L-alpha-glutamine
Homo sapiens
-
37C, pH and temperature not specified in the publication
0.00131
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]-N2-methylglycinamide
Homo sapiens
-
-
0.00189
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(2-chlorophenyl)methyl]glycinamide
Homo sapiens
-
-
0.00144
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]-N2-methylglycinamide
Homo sapiens
-
-
0.00172
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-fluorophenyl)methyl]glycinamide
Homo sapiens
-
-
0.00082
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]-N2-methylglycinamide
Homo sapiens
-
-
0.00128
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]-N2-methylglycinamide
Homo sapiens
-
-
0.00183
N2-benzyl-N-[(5-chloro-8-hydroxyquinolin-7-yl)(4-methylphenyl)methyl]glycinamide
Homo sapiens
-
-
0.00277
N2-[4-(acetylamino)phenyl]-N-[(5-chloro-8-hydroxyquinolin-7-yl)(3-nitrophenyl)methyl]glycinamide
Homo sapiens
-
-
0.899
tetracycline
Homo sapiens
-
pH and temperature not specified in the publication
0.0000038
TIMP-3
Homo sapiens
-
in 100 mM Tris-HCl, 100 mM NaCl, 0.01 mM CaCl2, 0.05% Brij, pH 7.5
-
0.0009
[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl](phenyl)acetic acid
Homo sapiens
-
-
0.0067
[(5E)-5-[[3,4-bis(benzyloxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
Homo sapiens
-
-
0.0013
[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl](phenyl)acetic acid
Homo sapiens
-
-
0.0111
[(5Z)-5-[[3-(3,4-dichlorophenoxy)phenyl]methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
Homo sapiens
-
-
additional information
2-[4-(benzyloxy)phenyl]-3-oxoisoindoline-4-carboxylic acid
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1200
-
partially purified recombinant enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9.5
-
-
8
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
constitutive Adamts5 expression in adult tissue
Manually annotated by BRENDA team
-
strong expression
Manually annotated by BRENDA team
constitutive Adamts5 expression in adult tissue
Manually annotated by BRENDA team
embryonic expression is scarce prior to 11.5 days of gestation (E11.5) and noted only in the floor plate of the developing brain at E9.5. After E11.5 there is continued expression in brain, especially in the choroid plexus, peripheral nerves, dorsal root ganglia, cranial nerve ganglia, spinal and cranial nerves, and neural plexuses of the gut. In addition to nerves, developing limbs have Adamts5 expression in skeletal muscle (from E13.5), tendons (from E16.5), and inter-digital mesenchyme of the developing autopod (E13.515.5)
Manually annotated by BRENDA team
-
U343, U373, U138 and U118
Manually annotated by BRENDA team
in the kidney, constitutive Adamts5 expression in adult tissue
Manually annotated by BRENDA team
-
ADAMTS-5 is the main aggrecanase in laryngeal squamous cell carcinoma
Manually annotated by BRENDA team
-
ADAMTS-4, EC 3.4.24.82, is the highest expressed aggrecanase in normal larynx
Manually annotated by BRENDA team
-
metastatic lymph node
Manually annotated by BRENDA team
lining the peritoneal, pericardial and pleural cavities, constitutive Adamts5 expression in adult tissue
Manually annotated by BRENDA team
of the peripheral and autonomic nervous system, constitutive Adamts5 expression in adult tissue
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
in bronchi and pancreatic ducts, constitutive Adamts5 expression in adult tissue. Expression of Adamts5 during neuromuscular development and in smooth muscle cells coincides with the broadly distributed proteoglycan versican, an ADAMTS5 substrate
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
late Golgi vesicles
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
-
SDS-PAGE, C-terminally truncated isoform of ADAMTS-5
64000
-
x * 64000, C-terminally processed recombinant mature enzyme, SDS-PAGE
70000
-
x * 70000, SDS-PAGE
73000
-
SDS-PAGE, deglycosylated full length recombinant human ADAMTS-5
75000
-
SDS-PAGE, glycosylated active form of ADAMTS-5
81000
-
recombinant enzyme, SDS-PAGE
85000
-
SDS-PAGE, full length recombinant human ADAMTS-5
105000
-
SDS-PAGE, pro-form of ADAMTS-5
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
a 30 kDa C-terminal truncated form, epitope mapping
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
proteolytic modification
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ADAMTS-5 catalytic domain in complex with inhibitor, vapor diffusion method, using 30% (w/v) PEG 3350 and 0.1 M Tris pH 8.5, at 22C
-
in complex with batimastat, vapour diffusion method at 18C using 10% PEG 8K, 0.2 M ammonium sulfate, and 0.1M MES (pH 6.5) as a precipitate
-
molecular dynamics simulations and multiway explorative data analysis on ADAMTS4 complexed with Marimastat and two cis-1(S)2(R)-amino-2-indanol ligands, and comparison with proteases MMP13, ADAMTS5. Determinant characteristics for ligand binding and selectivity among the three enzymes are to be found in the different protein conformation flexibility
-
sitting drop method, crystal structure of the catalytic domain of ADAMTS-5 in complex with marimastat, (2R)-N4-hydroxy-2-(3-hydroxybenzyl)-N1-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide or (3R)-N2-(cyclopropylmethyl)-N1-hydroxy-3-(3-hydroxybenzyl)-N4-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-L-aspartamide
-
vapour diffusion method with 25% (v/v) polyethylene glycol 3350, 200 mM ammonium acetate, 100 mM Tris, pH 8.5
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
anti-FLAG M2-agarose column chromatography, Macro-Prep 25 S resin chromatography, and
-
cation exchange chromatography and anion exchange chromatography
-
gel filtration
-
immunoprecipitation
-
M2-agarose column chromatography, Macro-Prep S resin column chromatography, and Sephacryl S-200 gel filtration
-
Ni-NTA affinity chromatography
-
partially, recombinant His-tagged enzyme from insect cells, 185fold
-
recombinant FLAG-tagged from insect Sf9 cells
-
Sephacryl S-200 HR gel filtration
-
Strep-Tactin affinity chromatography and Superdex-200 gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
correction of point mutations G577S and Q579R by overlap extension PCR, subcloning from FLAG-tagged construct in the baculovirus, cloning and expression of His-FLAG-tagged wild-type enzyme and mutants in insect cells via baculovirus infection
-
expressed in CHO cells
expressed in CHO/A2 cells
-
expressed in Drosophila SF9 cells
-
expressed in Escherichia coli MON208 cells
-
expressed in HEK-293-EBNA cells
-
expressed in HTB-94 human chondrosarcoma cell line
-
expressed in Sf9 cells
-
expression in Drosophila S2 cells
expression in neurons from cerebral cortex from Rattus norvegicus
-
expression of a recombinant interglobular domain of human aggrecan, residues 330YTGED to HLPGG458 tagged with glutathione S-transferase and FLAG, in Escherichia coli
-
expression of FLAG-tagged enzyme in Spodoptera frugiperda Sf9 cells via baculovirus infection, secretion of recombinant protein to the medium
-
recombinantly expressed
-
the catalytic domain of ADAMTS-5 comprising amino acids S263 to I480 preceded by a Met-Ala sequence and incorporating the single point mutation L282K is expressed in Escherichia coli
-
the first thrombospondin type 1 repeat is expressed in Escherichia coli strain BL21DE3
-
transfection of B16F1/B16F10 mouse melanoma cells
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
ADAMTS-5 expression is not regulated by interleukin-1 and tumor necrosis factor-alpha
-
Adamts5 mRNA is superinduced in Fgf2/ mice compared with Fgf2+/+ (fibroblast growth factor 2) mice 2 weeks following surgical destabilization of the medial meniscus
-
ADAMTS5 protein within cartilage increases following injury and with coculture
-
disruption of chondrocyte hyaluran receptor CD44-hyaluran interactions with hyaluran oligosaccharides induces the transcription of endopeptidases ADAMTS-4 and ADAMTS-5 in a time- and dose-dependent manner
-
fibroblast growth factor 2 inhibits ADAMTS-5 expression in isolated aortic smooth muscle cells and blocks the spontaneous release of ADAMTS-generated versican and aggrecan fragments from aortic explants
-
interleukin-1beta+OSM and tumor necrosis factor alpha+ OSM treatments induces a 17fold and 13fold increase in ADAMTS5 gene expression. Relatively little modulation in ADAMTS5 expression is observed in the presence of interleukin-1beta, tumor necrosis factor alpha or OSM alone
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E411A
-
active site mutant, presents similar tumor suppression activity as wild-type enzyme
E411Q
-
full length ADAMTS-5 active site mutant generated by point mutation
additional information
no enzyme activity in TS-5 deficient mice
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in 50 mM HEPES, pH 8.0, 2 mM oxidized glutathione, 50 mM arginine, 10 mM CaCl2, 0.2 mM ZnCl2, and 1% protease inhibitors, at room temperature
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
additional information
-
neurite extension mediated by the MAP kinase pathway, increased number of primary and secondary neurites