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(2R)-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido](phenyl)acetic acid
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(2S)-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido](phenyl)acetic acid
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1,1',1'',1'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrapropan-2-ol
1-(5-chloro-6-(trifluoromethoxy)-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid
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i.e. JNJ-42041935, 2-oxoglutarate analogue
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2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetamide
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chelates Fe2+ in a hexacoordinative mode through four nitrogens of the macrocycle and two oxygens in side arms
2,3-dihydroxypyridine
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2-(2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methylthiazol-4-yl)-N-(2-(diethylamino)ethyl)acetamide
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2-(2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-phenylthiazol-4-yl)-N-(2-(pyridin-2-yl)ethyl)acetamide
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2-(2-(5-cyano-3-hydroxypyridin-2-yl)-5-phenylthiazol-4-yl)-N-(2-(pyridin-2-yl)ethyl)acetamide
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2-hydroxypyridine 1-oxide
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2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(diethylamino)ethyl]acetamide
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2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
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2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-propylacetamide
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2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
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2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-(2-phenylethyl)acetamide
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2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[(1R)-2-hydroxy-1-phenylethyl]acetamide
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2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[(1S)-2-hydroxy-1-phenylethyl]acetamide
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2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
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2-[2-(5-cyano-3-hydroxypyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
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2-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido]-2-methylpropanoic acid
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3,3'-[(pyridin-2-ylmethyl)imino]dipropanenitrile
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noncompetitive inhibition
3,3'-[(pyridin-4-ylimino)bis(propane-3,1-diyliminomethanediyl)]diphenol
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noncompetitive inhibition
3,3'-[(pyridin-4-ylimino)bis[propane-3,1-diylnitrilo(Z)methylylidene]]diphenol
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noncompetitive inhibition
3,4-dihydroxybenzoate
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3,6,9-tris(naphthalen-1-ylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
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coordinates Fe2+ via triad or tetrad from nitrogen atoms of the parent ring, which leaves vacant position for other ligands binding
3-([1,1'-biphenyl]-4-yl)-8-[(3-methylpyridin-2-yl)methyl]-1-(pyrimidin-2-yl)-1,3,8-triazaspiro[4.5]decane-2,4-dione
compound stabilizes HIF-1alpha levels and is also active against lysine-specific demethylase KDM4A
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3-carboxy-4-oxo-3,4-dihydro-1,10-phenanthroline
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3-cyano-6-methyl-2(H)-pyridinone
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3-hydroxy-1,2-dimethyl-4(1H)-pyridinone
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3-hydroxy-2-methyl-4-pyrone
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3-hydroxypyridine-2-carbonyl-glycine
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3-[(1,3-benzoxazol-2-yl)carbamoyl]propanoic acid
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3-[(5-chloro-1,3-benzoxazol-2-yl)carbamoyl]propanoic acid
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4-hydroxy-2-(1H-pyrazol-1-yl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide
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4-hydroxy-N-[(1R)-2-hydroxy-1-phenylethyl]-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
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4-hydroxy-N-[(4-phenoxyphenyl)methyl]-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
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5-hydroxy-2-hydroxymethyl-4-pyrone
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5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid
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5-hydroxy-6-[4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]-1,3-thiazol-2-yl]pyridine-3-carbonitrile
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6-[5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-carboxylic acid
7-[(4-chlorophenyl)[(3-hydroxypyridin-2-yl)amino]methyl]quinolin-8-ol
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CO releasing molecule-2
i.e.CORM-2, [RuCl2(CO)3]2, in situ CO donor, reduces the hydroxylation of C-terminal and N-terminal oxygen-dependent degradation domains of HIF-1alpha
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desferrioxamine
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iron chelator
dimethyloxalyl glycine
mimicks 2-oxoglutarate binding mode
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DLDLEALA-L-3,4-dehydroproline-YIPADDDFQLR
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DLDLEALA-L-4-thioproline-YIPADDDFQLR
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DLDLEALA-L-piperidine-2-carboxylic acid-YIPADDDFQLR
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DLDLEALA-L-trans-4-fluoroproline-YIPADDDFQLR
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DLDLEALA-L-trans-4-hydroxyproline-YIPADDDFQLR
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ethyl 3,4-dihydroxybenzoate
iron chelator that can fit inside the active center
H2O2
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poor inhibition. Prolyl hydroxylase is less sensitive to peroxide, preferential inhibition of N803-hydroxylation by FIH, EC 1.14.11.30, compared with inhibition of P402/P564 hydroxylation by PHDs
IOX2
mimicks 2-oxoglutarate binding mode
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JNJ1935
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a prolyl-hydroxylase selective inhibitor. Low concentrations of JNJ1935 selectively inhibit PHDs, whereas higher concentrations inhibit all hydroxylases, including FIH, EC 1.14.11.30, in vitro and in vivo inhibition
N,N-dimethyl-5-[3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-ylsulfonyl]naphthalen-1-amine
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coordinates Fe2+ via triad or tetrad from nitrogen atoms of the parent ring, which leaves vacant position for other ligands binding
N-((3,4-dimethoxyphenyl)(8-hydroxyquinolin-7-yl)methyl)-2-phenylacetamide
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N-((3-hydroxy-6-chloroquinolin-2-yl)carbonyl)glycine
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N-(1-[[6-(4-chlorophenoxy)pyridin-3-yl]methyl]-4-hydroxy-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
clinical candidate as PHD2 inhibitor, promotes the production of erythropoietin following oral administration in mice and rats. The predicted half-life in humans is 1.3-5.6 h
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N-(4-hydroxy-1-[[4-(4-methylphenoxy)phenyl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
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N-(4-hydroxy-1-[[5-(4-methylphenoxy)pyridin-2-yl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
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N-(4-hydroxy-1-[[6-(4-methylphenoxy)pyridin-3-yl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
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N-(methoxyoxoacetyl)-glycine methyl ester
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a pan-hydroxylase inhibitor, in vitro and in vivo inhibition
N-([1,1'-biphenyl]-4-yl)-4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
compound stabilizes HIF-1alpha levels
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N-benzyl-2-[2-(3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamide
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N-benzyl-2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamide
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N-oxalyl-(2S)-alanine
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competed by 2-oxoglutarate, no inhibition by the enantiomer N-oxalyl-(2R)-alanine
N-[(1,3-dihydro-2-benzofuran-5-yl)methyl]-4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
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N-[(3,4-dimethoxyphenyl)(8-hydroxyquinolin-7-yl)methyl]-2-phenylacetamide
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optimized adaptaquin analog, shows no toxicity up to a 100fold increased range over EC50. The drug is ismetabolized by CYP3A4 and CYP2B6
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N-[([1,1'-biphenyl]-4-yl)methyl]-4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
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N-[1-[([1,1'-biphenyl]-4-yl)methyl]-4-hydroxy-2-oxo-1-azaspiro[5.5]undec-3-ene-3-carbonyl]glycine
lead compound for synthesis of orally administered agents for the treatment of renal anemia
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oxygen
the transiently overexpressed HPH-1 enzyme is inhibited by a low-oxygen environment
Pyridine-2,4-dicarboxylate
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RuCl3
inhibitor of PHD2 under the standard assay conditions in presence of 10 microM Fe(II). This effect can be alleviated by supplementing the enzymatic reaction mixture with excess Fe(II)
tert-butyl 6-(5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl)nicotinate
[(1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid
[(2E)-3-hydroxy-2-({[(naphthalen-2-yl)methanesulfonyl]acetyl}imino)-2,3-dihydro-1,3-thiazol-4-yl]acetic acid
[(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
[2-(3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetic acid
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[2-(3-hydroxypyridin-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl]acetic acid
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[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetic acid
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[2-(5-cyano-3-hydroxypyridin-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl]acetic acid
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[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido]acetic acid
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1,1',1'',1'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrapropan-2-ol
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noncompetitive inhibition
1,1',1'',1'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrapropan-2-ol
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chelates Fe2+ in a hexacoordinative mode through four nitrogens of the macrocycle and two oxygens in side arms
6-[5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-carboxylic acid
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6-[5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl]pyridine-3-carboxylic acid
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adaptaquin
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adaptaquin
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EC50 of ca 2 mM in HIF1 ODD-luc fusion reporter assay
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ciclopirox
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Cu2+
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binding analysis
dimethyloxalylglycine
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dimethyloxalylglycine
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2-oxoglutarate analogue
FG-4592
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FG-4592
mimicks 2-oxoglutarate binding mode
FG-4592
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i.e. roxadustat, 2-oxoglutarate analogue
N-oxalylglycine
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competed by 2-oxoglutarate
tert-butyl 6-(5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl)nicotinate
potent and selective inhibitor of isoform PHD2
tert-butyl 6-(5-oxo-4-(1H-1,2,3-triazol-1-yl)-2,5-dihydro-1H-pyrazol-1-yl)nicotinate
potent and selective inhibitor of isoform PHD2
[(1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
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[(1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
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[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid
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[(1-chloro-4-hydroxyisoquinoline-3-carbonyl)amino]acetic acid
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[(2E)-3-hydroxy-2-({[(naphthalen-2-yl)methanesulfonyl]acetyl}imino)-2,3-dihydro-1,3-thiazol-4-yl]acetic acid
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[(2E)-3-hydroxy-2-({[(naphthalen-2-yl)methanesulfonyl]acetyl}imino)-2,3-dihydro-1,3-thiazol-4-yl]acetic acid
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[(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
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[(4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonyl)amino]acetic acid
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additional information
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the peptide inhibitors consist of amino acids identical to those in the CODD556-575 except the 564 proline residue, and target the C-terminal oxygen-dependent degradation domain binding site in the PHD2 active pocket. Specific inhibition of PHD2, no inhibition of FIH, EC 1.14.11.30
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additional information
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temporal dynamics of hydroxylase inhibition, overview
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additional information
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polynitrogen compound as HIF-1alpha PHD3 inhibitors, the metal complexes of these polynitrogen compounds cannot inhibit the catalytical activity of PHD3, overview. The inhibitory mechanism of PHD3 activity by polynitrogen compounds is due to their binding to iron to form stable coordination complexes
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additional information
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screening of iron chelators pyridines, hydroxypyrones/hydroxypyridinones, and catechols as inhibitors for PHD2, analysis of selectivity of the inhibitors for PHD2 compared to FIH, EC 1.14.11.30. Ligand binding kinetics and structural analysis, overview. Representative inhibitors bind to the metal center in PHD2 as an 2-oxoglutarate mimic
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additional information
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inhibition of the recombinant human PHD3 activity by tetraazamacrocycles, overview
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additional information
compounds with a 3-carbamoylpropanoic acids-containing benzoxazole moiety are inhibitors of PHD-2. However, neither the acids nor their respective ethyl esters upregulate HIF-1alpha levels in cells
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