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Literature summary extracted from

  • Kaku, T.; Matsunaga, N.; Ojida, A.; Tanaka, T.; Hara, T.; Yamaoka, M.; Kusaka, M.; Tasaka, A.
    17,20-lyase inhibitors. Part 4: design, synthesis and structure-activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors (2011), Bioorg. Med. Chem., 19, 1751-1770.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.19 (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
 Rattus norvegicus
1.14.14.19 1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
 Homo sapiens
1.14.14.19 1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
 Homo sapiens
1.14.14.19 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Homo sapiens
1.14.14.19 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
 Rattus norvegicus
1.14.14.19 abiraterone acetate
-
 Homo sapiens
1.14.14.19 abiraterone acetate
-
 Rattus norvegicus
1.14.14.19 methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
 Homo sapiens
1.14.14.19 methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
-
 Rattus norvegicus
1.14.14.19 N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
 Homo sapiens
1.14.14.19 N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
-
 Rattus norvegicus
1.14.14.19 N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
 Homo sapiens
1.14.14.19 N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
-
 Rattus norvegicus
1.14.14.19 N-[4'-[(1S)-1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]biphenyl-3-yl]acetamide
-
 Rattus norvegicus
1.14.14.19 N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
 Homo sapiens
1.14.14.19 N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
-
 Rattus norvegicus
1.14.14.19 YM-116
-
 Homo sapiens
1.14.14.19 YM-116
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.14.14.19 microsome
-
 Rattus norvegicus
-
-

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.19 Homo sapiens
-
-
-
1.14.14.19 Rattus norvegicus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.19 testis
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.19 17alpha-hydroxyprogesterone + AH2 + O2
-
 Homo sapiens ?
-
 ?
1.14.14.19 17alpha-hydroxyprogesterone + AH2 + O2
-
 Rattus norvegicus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.19 17,20-lyase
-
 Homo sapiens
1.14.14.19 17,20-lyase
-
 Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.19 cytochrome b5
-
 Homo sapiens
1.14.14.19 cytochrome b5
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.14.19 0.000006
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
1.14.14.19 0.00001
-
 IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
1.14.14.19 0.00001
-
 IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.00001
-
 IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.00001
-
 IC50 above 0.00001 mM, in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000011
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
1.14.14.19 0.000011
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
1.14.14.19 0.000012
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
1.14.14.19 0.000012
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
1.14.14.19 0.000013
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
1.14.14.19 0.000014
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
1.14.14.19 0.000015
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000015
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000016
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
1.14.14.19 0.000018
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000019
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
1.14.14.19 0.000019
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens (-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000021
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
1.14.14.19 0.000022
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.000024
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
1.14.14.19 0.000028
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
1.14.14.19 0.000028
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
1.14.14.19 0.000029
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
1.14.14.19 0.00003
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
1.14.14.19 0.000036
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
1.14.14.19 0.000036
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
1.14.14.19 0.000038
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
1.14.14.19 0.000039
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
1.14.14.19 0.000039
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
1.14.14.19 0.000042
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
1.14.14.19 0.000043
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
1.14.14.19 0.000046
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
1.14.14.19 0.00006
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.00007
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
1.14.14.19 0.000075
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
1.14.14.19 0.000091
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
1.14.14.19 0.00011
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.00016
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
1.14.14.19 0.00018
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
1.14.14.19 0.0002
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens 1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
1.14.14.19 0.0002
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Rattus norvegicus 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
1.14.14.19 0.00027
-
 in 75 mM phosphate buffer (pH 7.4), at 37°C Homo sapiens (+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one