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Literature summary extracted from

  • Xu, Y.L.; Lin, H.Y.; Ruan, X.; Yang, S.G.; Hao, G.F.; Yang, W.C.; Yang, G.F.
    Synthesis and bioevaluation of pyrazole-benzimidazolone hybrids as novel human 4-hydroxyphenylpyruvate dioxygenase inhibitors (2015), Eur. J. Med. Chem., 92, 427-438 .
    View publication on PubMed

Application

EC Number Application Comment Organism
1.13.11.27 drug development 4-hydroxyphenylpyruvate dioxygenase (HPPD), an essential enzyme in tyrosine catabolism, is an important target for treating type I tyrosinemia Homo sapiens
1.13.11.27 medicine 4-hydroxyphenylpyruvate dioxygenase (HPPD), an essential enzyme in tyrosine catabolism, is an important target for treating type I tyrosinemia Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.27 gene HPD, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3) Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.27 1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione NTBC, a commercial HPPD inhibitor in clinical use Homo sapiens
1.13.11.27 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens
1.13.11.27 additional information synthesis of pyrazole-benzimidazolone hybrids from DNS869 and droperidol, bioevaluation of pyrazole-benzimidazolone hybrids as human 4-hydroxyphenylpyruvate dioxygenase inhibitors, overview Homo sapiens
1.13.11.27 tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
-
 Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2 Homo sapiens
-
 homogentisate + CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.27 Homo sapiens P32754
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.13.11.27 recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and ultrafiltration Homo sapiens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.27 4-hydroxyphenylpyruvate + O2
-
 Homo sapiens homogentisate + CO2
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.27 HPD
-
 Homo sapiens
1.13.11.27 HPPD
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.13.11.27 30
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.13.11.27 7
-
 assay at Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.27 0.000021
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1,3-diethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000022
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000022
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000039
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00004
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d]imidazol-2(3H)-one
1.13.11.27 0.000059
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000061
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000064
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.000077
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.0001
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens tert-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.0001
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens Cyclopropyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00013
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-cyclopentyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00013
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-benzyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00014
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00015
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-tert-butyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00017
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-butyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00022
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-cyclopropyl-3-ethyl-5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00025
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00064
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00067
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens enzyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00068
-
 pH 7.0, 30°C, recombinant His-tagged enzyme Homo sapiens 2-(2-nitro-4-trifluoromethylbenzoyl)cyclohexane-1,3-dione
1.13.11.27 0.00072
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,3-dipropyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00074
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00088
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00093
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-cyclopentyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00094
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00094
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1,3-diethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00097
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00097
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 3-ethyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00099
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 1-tert-butyl-5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1H-benzo [d] imidazol-2(3H)-one
1.13.11.27 0.00099
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-p-tolyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00103
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-3-methyl-1-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00119
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isopropyl-3-propyl-1H-benzo[d] imidazol-2(3H)-one
1.13.11.27 0.00271
-
 recombinant His-tagged enzyme, pH 7.0, 30°C Homo sapiens 5-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1-isobutyl-3-methyl-1H-benzo[d] imidazol-2(3H)-one

General Information

EC Number General Information Comment Organism
1.13.11.27 malfunction inhibition of HPPD can effectively alleviate the symptoms of type I tyrosinemia Homo sapiens
1.13.11.27 metabolism 4-ydroxyphenylpyruvate dioxygenase (HPPD) is an essential enzyme in tyrosine catabolism Homo sapiens