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1.14.11.29: hypoxia-inducible factor-proline dioxygenase

This is an abbreviated version!
For detailed information about hypoxia-inducible factor-proline dioxygenase, go to the full flat file.

Word Map on EC 1.14.11.29

Reaction

hypoxia-inducible factor-L-proline
+
2-oxoglutarate
 +
O2
=
hypoxia-inducible factor-(4R)-4-hydroxy-L-proline
 +
succinate
 +
CO2

Synonyms

Egl nine homolog 1, EGLN, EGLN1, Egln2, EGLN3, factor inhibiting HIF, FIH, HIF hydroxylase, HIF prolyl, HIF prolyl 4-hydroxylase, HIF prolyl hydroxylase, HIF-1alpha PHD3, HIF-1alpha prolyl hydroxylase 3, HIF-alpha prolyl-hydroxylase, HIF-P4H-1, HIF-P4H-2, HIF-P4H-3, HIF-PH, Hif-prolyl hydroxylase, HIF-prolyl hydroxylase domain 2, HIF-prolyl hydroxylase-2, HPH-1, HPH-2, HPH-3, hydroxylase domain enzyme, hypoxia-inducible factor prolyl hydroxylase 2, hypoxia-inducible factor prolyl hydroxylase domain 2, P4H-TM, PHD, PHD1, PHD2, PHD3, proline hydroxylase domain 2, prolyl 4-hydroxylase, prolyl hydroxylase, prolyl hydroxylase domain, prolyl hydroxylase domain protein, prolyl hydroxylase domain protein 2, prolyl hydroxylase-2, prolyl-4-hydroxylase 2, prolyl-4-hydroxylase domain 2, transmembrane prolyl 4-hydroxylase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.11 With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
                1.14.11.29 hypoxia-inducible factor-proline dioxygenase

Inhibitors

Inhibitors on EC 1.14.11.29 - hypoxia-inducible factor-proline dioxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2R)-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido](phenyl)acetic acid
-
-
(2S)-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido](phenyl)acetic acid
-
-
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
-
i.e. JNJ-42041935, 2-oxoglutarate analogue
-
2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetamide
-
chelates Fe2+ in a hexacoordinative mode through four nitrogens of the macrocycle and two oxygens in side arms
2,3-dihydroxypyridine
-
-
2-(2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methylthiazol-4-yl)-N-(2-(diethylamino)ethyl)acetamide
-
-
2-(2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-phenylthiazol-4-yl)-N-(2-(pyridin-2-yl)ethyl)acetamide
-
-
2-(2-(5-cyano-3-hydroxypyridin-2-yl)-5-phenylthiazol-4-yl)-N-(2-(pyridin-2-yl)ethyl)acetamide
-
-
2-hydroxypyridine 1-oxide
-
-
2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(diethylamino)ethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-propylacetamide
-
-
2-[2-(5-cyano-3-hydroxy-4-methylpyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-(2-phenylethyl)acetamide
-
-
2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[(1R)-2-hydroxy-1-phenylethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[(1S)-2-hydroxy-1-phenylethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
-
-
2-[2-(5-cyano-3-hydroxypyridin-2-yl)-5-methyl-1,3-thiazol-4-yl]-N-[2-(pyridin-2-yl)ethyl]acetamide
-
-
2-[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido]-2-methylpropanoic acid
-
-
3,3'-[(pyridin-2-ylmethyl)imino]dipropanenitrile
-
noncompetitive inhibition
3,3'-[(pyridin-4-ylimino)bis(propane-3,1-diyliminomethanediyl)]diphenol
-
noncompetitive inhibition
3,3'-[(pyridin-4-ylimino)bis[propane-3,1-diylnitrilo(Z)methylylidene]]diphenol
-
noncompetitive inhibition
3,4-dihydroxybenzoate
-
-
3,6,9-tris(naphthalen-1-ylmethyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene
-
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
-
3-carboxy-4-oxo-3,4-dihydro-1,10-phenanthroline
-
3-cyano-6-methyl-2(H)-pyridinone
-
-
3-hydroxy-1,2-dimethyl-4(1H)-pyridinone
-
-
3-hydroxy-2-methyl-4-pyrone
-
-
3-hydroxypyridine-2-carbonyl-glycine
-
3-[(1,3-benzoxazol-2-yl)carbamoyl]propanoic acid
-
-
3-[(5-chloro-1,3-benzoxazol-2-yl)carbamoyl]propanoic acid
-
-
4-hydroxy-2-(1H-pyrazol-1-yl)-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-5-carboxamide
-
-
4-hydroxy-N-[(1R)-2-hydroxy-1-phenylethyl]-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
-
-
4-hydroxy-N-[(4-phenoxyphenyl)methyl]-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
-
-
4-methylcatechol
-
-
4-nitrocatechol
-
-
4-tert-butylcatechol
-
-
5-hydroxy-2-hydroxymethyl-4-pyrone
-
-
5-hydroxy-4-oxo-4H-pyran-2-carboxylic acid
-
-
5-hydroxy-6-[4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]-1,3-thiazol-2-yl]pyridine-3-carbonitrile
-
-
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
-
adaptaquin
-
AKB-6548
-
-
BAY85-3934
-
-
ciclopirox
ciclopirox olamine
-
-
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
-
cobalt chloride
-
-
deferoxamine
-
-
desferrioxamine
-
iron chelator
dimethyloxalyl glycine
mimicks 2-oxoglutarate binding mode
-
dimethyloxalylglycine
DLDLEALA-L-3,4-dehydroproline-YIPADDDFQLR
-
-
DLDLEALA-L-4-thioproline-YIPADDDFQLR
-
-
DLDLEALA-L-piperidine-2-carboxylic acid-YIPADDDFQLR
-
-
DLDLEALA-L-trans-4-fluoroproline-YIPADDDFQLR
-
-
DLDLEALA-L-trans-4-hydroxyproline-YIPADDDFQLR
-
-
ethyl 3,4-dihydroxybenzoate
iron chelator that can fit inside the active center
FG-0041
-
-
FG-4497
-
-
-
FG-4592
FKBP38
-
-
-
GSK1278863
-
-
H2O2
-
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
-
JNJ1935
-
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
L-mimosine
-
-
Mn2+
-
-
Morg-1
-
-
-
N,N-dimethyl-5-[3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-ylsulfonyl]naphthalen-1-amine
-
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
-
N-((3-hydroxy-6-chloroquinolin-2-yl)carbonyl)glycine
-
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
-
N-(4-hydroxy-1-[[4-(4-methylphenoxy)phenyl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
-
-
N-(4-hydroxy-1-[[5-(4-methylphenoxy)pyridin-2-yl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
-
-
N-(4-hydroxy-1-[[6-(4-methylphenoxy)pyridin-3-yl]methyl]-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonyl)glycine
-
-
N-(methoxyoxoacetyl)-glycine methyl ester
-
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
-
N-benzyl-2-[2-(3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamide
-
-
N-benzyl-2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamide
-
-
N-oxalyl-(2S)-alanine
-
competed by 2-oxoglutarate, no inhibition by the enantiomer N-oxalyl-(2R)-alanine
N-oxalylglycine
N-[(1,3-dihydro-2-benzofuran-5-yl)methyl]-4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
-
-
N-[(3,4-dimethoxyphenyl)(8-hydroxyquinolin-7-yl)methyl]-2-phenylacetamide
-
optimized adaptaquin analog, shows no toxicity up to a 100fold increased range over EC50. The drug is ismetabolized by CYP3A4 and CYP2B6
-
N-[([1,1'-biphenyl]-4-yl)methyl]-4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxamide
-
-
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
-
oxalylglycine
-
oxygen
the transiently overexpressed HPH-1 enzyme is inhibited by a low-oxygen environment
PN-3602
-
-
-
Pyridine-2,4-dicarboxylate
-
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
TM6008
-
-
TM6089
-
-
Zn2+
-
-
[(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
-
-
[2-(3-hydroxypyridin-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl]acetic acid
-
-
[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetic acid
-
-
[2-(5-cyano-3-hydroxypyridin-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl]acetic acid
-
-
[2-[2-(5-cyano-3-hydroxypyridin-2-yl)-1,3-thiazol-4-yl]acetamido]acetic acid
-
-
additional information
-