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Literature summary extracted from

  • Calil, F.A.; David, J.S.; Chiappetta, E.R.C.; Fumagalli, F.; Mello, R.B.; Leite, F.H.A.; Castilho, M.S.; Emery, F.S.; Nonato, M.C.
    Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase (2019), Eur. J. Med. Chem., 167, 357-366 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.3.5.2 1,4-benzoquinone 3.9fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 1,4-benzoquinone 3.9fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-(2,3-dichloroanilino)-3-hydroxynaphthalene-1,4-dione 6.5fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-(2,3-dichloroanilino)-3-hydroxynaphthalene-1,4-dione 6.5fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-(2,6-dimethylanilino)-3-hydroxynaphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-(2,6-dimethylanilino)-3-hydroxynaphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-(2-chloroanilino)-3-hydroxynaphthalene-1,4-dione 10.4fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-(2-chloroanilino)-3-hydroxynaphthalene-1,4-dione 10.4fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-(3-chloroanilino)-3-hydroxynaphthalene-1,4-dione 7fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-(3-chloroanilino)-3-hydroxynaphthalene-1,4-dione 7fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-(4-chloroanilino)-3-hydroxynaphthalene-1,4-dione 2.9fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-(4-chloroanilino)-3-hydroxynaphthalene-1,4-dione 2.9fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-(4-fluoroanilino)-3-hydroxynaphthalene-1,4-dione 3fold selectivity for human over Schistosoma mansoni enzyme Homo sapiens
1.3.5.2 2-(4-fluoroanilino)-3-hydroxynaphthalene-1,4-dione 3fold selectivity for human over Schistosoma mansoni enzyme Schistosoma mansoni
1.3.5.2 2-anilino-3-hydroxynaphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-anilino-3-hydroxynaphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-chloro-3-(methylamino)naphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-chloro-3-(methylamino)naphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-hydroxy-3-(3-methylbutyl)naphthalene-1,4-dione 30.8fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-hydroxy-3-(3-methylbutyl)naphthalene-1,4-dione 30.8fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-hydroxy-3-(4-methoxyanilino)naphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-hydroxy-3-(4-methoxyanilino)naphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-hydroxy-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione 9.6fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-hydroxy-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione 9.6fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-hydroxy-3-[3-(trifluoromethyl)anilino]naphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-hydroxy-3-[3-(trifluoromethyl)anilino]naphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-hydroxy-3-[4-(4-nitrophenyl)piperazin-1-yl]naphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-hydroxy-3-[4-(4-nitrophenyl)piperazin-1-yl]naphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-methylcyclohexa-2,5-diene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-tert-butylcyclohexa-2,5-diene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-[(2,3-dihydro-1,4-benzodioxin-6-yl)amino]-3-hydroxynaphthalene-1,4-dione 2fold selectivity for human over Schistosoma mansoni enzyme Homo sapiens
1.3.5.2 2-[(2,3-dihydro-1,4-benzodioxin-6-yl)amino]-3-hydroxynaphthalene-1,4-dione 2fold selectivity for human over Schistosoma mansoni enzyme Schistosoma mansoni
1.3.5.2 2-[(2H-1,3-benzodioxol-5-yl)amino]-3-hydroxynaphthalene-1,4-dione
-
 Homo sapiens
1.3.5.2 2-[(2H-1,3-benzodioxol-5-yl)amino]-3-hydroxynaphthalene-1,4-dione
-
 Schistosoma mansoni
1.3.5.2 2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione 4.1fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione 4.1fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 2-[4-(4-chlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione 20.3fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 2-[4-(4-chlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione 20.3fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzene-1-sulfonate 4.0fold selectivity for human over Schistosoma mansoni enzyme Homo sapiens
1.3.5.2 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzene-1-sulfonate 4.0fold selectivity for human over Schistosoma mansoni enzyme Schistosoma mansoni
1.3.5.2 atovaquone 6.3fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 atovaquone 6.3fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 brequinar 540fold selectivity for human over Schistosoma mansoni enzyme Homo sapiens
1.3.5.2 brequinar 540fold selectivity for human over Schistosoma mansoni enzyme Schistosoma mansoni
1.3.5.2 isolapachol 8.3fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 isolapachol 8.3fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 Lapachol 5.3fold selectivity for Schistosoma mansoni over human enzyme Homo sapiens
1.3.5.2 Lapachol 5.3fold selectivity for Schistosoma mansoni over human enzyme Schistosoma mansoni
1.3.5.2 Lawsone
-
 Homo sapiens
1.3.5.2 Lawsone
-
 Schistosoma mansoni
1.3.5.2 teriflunomide 160fold selectivity for human over Schistosoma mansoni enzyme Homo sapiens
1.3.5.2 teriflunomide 160fold selectivity for human over Schistosoma mansoni enzyme Schistosoma mansoni
1.3.5.2 [[3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]oxy]acetonitrile
-
 Homo sapiens
1.3.5.2 [[3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]oxy]acetonitrile
-
 Schistosoma mansoni

Organism

EC Number Organism UniProt Comment Textmining
1.3.5.2 Homo sapiens Q02127
-
-
1.3.5.2 Schistosoma mansoni G4VFD7
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.3.5.2 dihydroorotate + coenzyme Q0
-
 Homo sapiens orotate + reduced coenzyme Q0
-
 ?
1.3.5.2 dihydroorotate + coenzyme Q0
-
 Schistosoma mansoni orotate + reduced coenzyme Q0
-
 ?

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.3.5.2 0.000019
-
 pH 8.2, 25°C Schistosoma mansoni Lapachol
1.3.5.2 0.000023
-
 pH 8.2, 25°C Schistosoma mansoni 2-hydroxy-3-(3-methylbutyl)naphthalene-1,4-dione
1.3.5.2 0.000037
-
 pH 8.2, 25°C Homo sapiens brequinar
1.3.5.2 0.000078
-
 pH 8.2, 25°C Schistosoma mansoni 2-(2-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0001
-
 pH 8.2, 25°C Homo sapiens Lapachol
1.3.5.2 0.000108
-
 pH 8.2, 25°C Homo sapiens 2-hydroxy-3-[3-(trifluoromethyl)anilino]naphthalene-1,4-dione
1.3.5.2 0.000111
-
 pH 8.2, 25°C Schistosoma mansoni 2-hydroxy-3-[3-(trifluoromethyl)anilino]naphthalene-1,4-dione
1.3.5.2 0.000123
-
 pH 8.2, 25°C Homo sapiens 2-(2,3-dichloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000129
-
 pH 8.2, 25°C Schistosoma mansoni 2-(3-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000185
-
 pH 8.2, 25°C Schistosoma mansoni 2-(4-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.00019
-
 pH 8.2, 25°C Schistosoma mansoni 2-(2,3-dichloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.00028
-
 pH 8.2, 25°C Schistosoma mansoni 2-[4-(4-chlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000312
-
 pH 8.2, 25°C Homo sapiens teriflunomide
1.3.5.2 0.00033
-
 pH 8.2, 25°C Homo sapiens 2-(4-fluoroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.00038
-
 pH 8.2, 25°C Schistosoma mansoni 2-hydroxy-3-[4-(4-nitrophenyl)piperazin-1-yl]naphthalene-1,4-dione
1.3.5.2 0.00043
-
 pH 8.2, 25°C Schistosoma mansoni atovaquone
1.3.5.2 0.00044
-
 pH 8.2, 25°C Schistosoma mansoni 2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000541
-
 pH 8.2, 25°C Homo sapiens 2-(4-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000709
-
 pH 8.2, 25°C Homo sapiens 2-hydroxy-3-(3-methylbutyl)naphthalene-1,4-dione
1.3.5.2 0.000711
-
 pH 8.2, 25°C Schistosoma mansoni 2-hydroxy-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione
1.3.5.2 0.000808
-
 pH 8.2, 25°C Homo sapiens 2-(2-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.000911
-
 pH 8.2, 25°C Homo sapiens 2-(3-chloroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.001
-
 pH 8.2, 25°C Schistosoma mansoni 2-(4-fluoroanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.00105
-
 pH 8.2, 25°C Homo sapiens 2-[(2,3-dihydro-1,4-benzodioxin-6-yl)amino]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0012
-
 pH 8.2, 25°C Schistosoma mansoni isolapachol
1.3.5.2 0.0018
-
 pH 8.2, 25°C Homo sapiens 2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0021
-
 pH 8.2, 25°C Schistosoma mansoni 2-anilino-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0021
-
 pH 8.2, 25°C Schistosoma mansoni 2-[(2,3-dihydro-1,4-benzodioxin-6-yl)amino]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0025
-
 pH 8.2, 25°C Schistosoma mansoni [[3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl]oxy]acetonitrile
1.3.5.2 0.0026
-
 pH 8.2, 25°C Homo sapiens 2-anilino-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0027
-
 pH 8.2, 25°C Homo sapiens atovaquone
1.3.5.2 0.0036
-
 pH 8.2, 25°C Homo sapiens 2-[(2H-1,3-benzodioxol-5-yl)amino]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0046
-
 pH 8.2, 25°C Homo sapiens 2-[4-(4-chlorophenyl)piperazin-1-yl]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0047
-
 pH 8.2, 25°C Schistosoma mansoni 2-hydroxy-3-(4-methoxyanilino)naphthalene-1,4-dione
1.3.5.2 0.0055
-
 pH 8.2, 25°C Schistosoma mansoni 2-[(2H-1,3-benzodioxol-5-yl)amino]-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.0068
-
 pH 8.2, 25°C Homo sapiens 2-hydroxy-3-(4-phenylpiperazin-1-yl)naphthalene-1,4-dione
1.3.5.2 0.0079
-
 pH 8.2, 25°C Homo sapiens 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzene-1-sulfonate
1.3.5.2 0.0088
-
 pH 8.2, 25°C Schistosoma mansoni 1,4-benzoquinone
1.3.5.2 0.0099
-
 pH 8.2, 25°C Schistosoma mansoni 2-(2,6-dimethylanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.01
-
 pH 8.2, 25°C Homo sapiens 2-(2,6-dimethylanilino)-3-hydroxynaphthalene-1,4-dione
1.3.5.2 0.01
-
 pH 8.2, 25°C Homo sapiens isolapachol
1.3.5.2 0.02
-
 pH 8.2, 25°C Schistosoma mansoni brequinar
1.3.5.2 0.029
-
 pH 8.2, 25°C Schistosoma mansoni Lawsone
1.3.5.2 0.0314
-
 pH 8.2, 25°C Schistosoma mansoni 3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl 4-methylbenzene-1-sulfonate
1.3.5.2 0.034
-
 pH 8.2, 25°C Homo sapiens 1,4-benzoquinone
1.3.5.2 0.05
-
 pH 8.2, 25°C Schistosoma mansoni teriflunomide
1.3.5.2 0.057
-
 pH 8.2, 25°C Schistosoma mansoni 2-methylcyclohexa-2,5-diene-1,4-dione
1.3.5.2 0.079
-
 pH 8.2, 25°C Schistosoma mansoni 2-chloro-3-(methylamino)naphthalene-1,4-dione
1.3.5.2 0.768
-
 pH 8.2, 25°C Schistosoma mansoni 2-tert-butylcyclohexa-2,5-diene-1,4-dione