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(1-hydroxy-2-phenylethane-1,1-diyl)bis(phosphonic acid)
-
(1-hydroxy-2-[3'-[(naphthalene-2-sulfonyl)amino][1,1'-biphenyl]-3-yl]ethane-1,1-diyl)bis(phosphonic acid)
-
(2E,6E)-farnesyl thiodiphosphate
(2E,6E,10E)-4-methylfarnesyl diphosphate
-
competitive inhibitor against (2Z,6E,10E)-geranylgeranyl diphosphate
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
(2Z)-2-hydroxy-4-oxo-4-[[3-(3-phenoxyphenyl)propyl]amino]but-2-enoic acid
-
(2Z)-2-hydroxy-4-[3-[3-(octyloxy)phenoxy]phenyl]-4-oxobut-2-enoic acid
-
(2Z)-2-hydroxy-4-[4-(octyloxy)phenyl]-4-oxobut-2-enoic acid
-
(2Z)-4-([3-[3-(hexyloxy)phenyl]propyl]amino)-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[3-[3-(decyloxy)phenoxy]phenyl]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[[3-([1,1'-biphenyl]-3-yl)propyl]amino]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z,6E,10E)-4-methyl-geranylgeranyl diphosphate
-
allylic substrate homologue, competitive inhibitor against the allylic primer. It also acts as a strong noncompetitive inhibitor against isopentenyl diphosphate
(4aS,8aS)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro[1,6]naphthyridine-3-carboxylic acid (4-piperidin-1-ylphenyl)amide
-
-
(5-bromo-2-[[3-(octyloxy)phenyl]methoxy]phenyl)phosphonic acid
-
-
(E)-3-methyl-3-pentenyl diphosphate
-
reactive as substrate and competitive inhibition profile
(E,E)-[1-3H]-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
-
-
(S)-farnesyl thiodiphosphate
-
an extremely poor substrate for UPPs
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
1,4-bis(6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indol-2-yl)benzene
1-(2-hydroxy-2,2-diphosphonoethyl)-3-phenylpyridin-1-ium
-
1-[3-fluoro-4-(4-[[2-(thiophen-2-yl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl)phenyl]ethan-1-one
-
1-[[3-(hexyloxy)phenyl]methyl]-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
2,6-bis(5-bromo-2-hydroxyphenyl)-3,5-dimethylpiperidin-4-one
-
2-(2-[[5-(1-benzofuran-2-yl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl]acetamido)benzoic acid
-
2-hydroxy-6-(undecyloxy)benzoic acid
-
2-methoxy-6-[3-(octyloxy)benzamido]benzoic acid
-
-
2-[3-(decyloxy)benzamido]-5-nitrobenzoic acid
-
-
2-[3-(hexyloxy)benzamido]benzoic acid
-
-
2-[3-(octyloxy)benzamido]-5-(trifluoromethoxy)benzoic acid
-
-
2-[3-(octyloxy)benzamido]-5-phosphonobenzoic acid
-
-
2-[3-(octyloxy)benzamido]benzoic acid
-
-
2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethan-1-amine
-
2-[methyl[3-(octyloxy)benzoyl]amino]benzoic acid
-
-
2-[[(2E)-2-cyano-3-[1-[(naphthalen-1-yl)methyl]-1H-indol-3-yl]prop-2-enoyl]amino]benzoic acid
-
2-[[(2E)-2-cyano-3-[3-[(4-fluorophenyl)methoxy]phenyl]prop-2-enoyl]amino]benzoic acid
-
2-[[3-(3,4-dimethylphenoxy)phenyl]carbamoyl]benzoic acid
-
3-(2-chlorophenyl)-5-methyl-N-[4-(propan-2-yl)phenyl]-1,2-oxazole-4-carboxamide
-
3-(2-chlorophenyl)-N-(4-isopropylphenyl-5-methylisoxazole-4-carboxamide)
i.e. UK-106051, a drug-like UPPs inhibitor, UK-106051 binds to a site in the middle of this binding cleft. Substrates FPP and IPP cannot bind simultaneously to UPPs-inhibitor binary complexes
3-(4-chlorophenyl)-N'-[(2,4-dihydroxyphenyl)methyl]-1H-pyrazole-5-carbohydrazide
-
3-(dibenzo[b,d]furan-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-2-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-3-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-3-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-desmethyl (2Z,6E,10E)-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate
3-desmethyl farnesyl diphosphate
-
competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate; competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-desmethyl Z-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-ethoxy-2-methyl-6-(4-phenyl-1H-pyrazol-3-yl)phenol
-
3-fluoro-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-[(5Z)-5-[[5-(2,4-dichlorophenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
-
3-[3-(hexyloxy)benzamido]-4-hydroxybenzoic acid
-
-
3-[3-(octyloxy)benzamido]benzene-1,2-dicarboxylic acid
-
-
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
4,5-difluoro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
4-(benzyloxy)-3-bromo-5-methoxy-N-[(oxolan-2-yl)methyl]benzamide
-
4-(dibenzo[b,d]furan-4-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
4-([1,1'-biphenyl]-3-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
4-([1,1'-biphenyl]-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
4-[3-(octyloxy)benzamido]benzene-1,3-dicarboxylic acid
-
-
4-[3-[([1,1'-biphenyl]-4-carbonyl)amino]phenoxy]benzene-1,2-dicarboxylic acid
-
5-(diethoxyphosphoryl)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-(methanesulfonyl)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-([5-[(1H-benzimidazol-2-yl)sulfanyl]furan-2-yl]methylidene)-1,3-diazinane-2,4,6-trione
-
5-benzyl-3-[1-(4-cyclohexylanilino)ethenyl]-4-hydroxy-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-5-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-cyclohexylphenyl)amide
-
-
5-benzyl-N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-benzyl-N-[4-(hexyloxy)phenyl]-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-bromo-2-[3-(3,3-dimethylbut-1-yn-1-yl)benzamido]benzoic acid
-
-
5-bromo-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-bromo-2-[4-(6-chloro-2,3-dihydro-1H-indole-1-sulfonyl)benzamido]benzoic acid
-
5-chloro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-fluoro-2-[3-(hexyloxy)benzamido]benzoic acid
-
-
5-fluoro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-hydroxy-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-methoxy-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-methoxy-4-(2-methoxyethoxy)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-[3-(octyloxy)benzamido]benzene-1,3-dicarboxylic acid
-
-
6-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate
-
competitive inhibitor, substrate analogue prepared and utilized to study ligand interactions
7-(azepan-1-yl)-3-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine
-
diphosphate
product inhibition
isopentyl thiodiphosphate
-
substrate analogue
Mg2+
inhibitory at high concentrations of e.g. 50 mM; inhibitory at high concentrations of e.g. 50 mM
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
N-(2-carbamoylphenyl)-3-(octyloxy)benzamide
-
-
N-(3,5-dichlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(3-amino-3-oxopropyl)-1-benzyl-5-(4-methylphenyl)-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(3-amino-3-oxopropyl)-5-(1-benzothiophen-5-yl)-1-benzyl-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(4-bromo-2-carbamoylphenyl)-3,4-bis(2-methoxyethoxy)benzamide
-
-
N-(4-chlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-([1,1'-biphenyl]-4-yl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
N-[3-[3,4-di(prop-1-en-2-yl)phenoxy]phenyl][1,1'-biphenyl]-4-carboxamide
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
N1,N4-bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-nitrobenzene-1,4-dicarboxamide
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'- (3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-3(-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
NH4+
-
20 mM, 20% inhibition
S-farnesyl thiodiphosphate
-
-
SO42-
competitive inhibitor with respect to (2E,6E)-farnesyl diphosphate; competitive inhibitor with respect to farnesyl diphosphate
viridicatumtoxin B
the inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), via inhibition of the UPP synthase activity
[(5Z)-5-[[5-(4-chloro-2-methylphenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
-
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
[1-hydroxy-2-(pyridin-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(4)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-2-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-[([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)oxy]ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(2),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[2-([1,1'-biphenyl]-3-yl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxy-1,1-ethanediyl]bis(phosphonic acid)
i.e. BPH-629. A pharmacophore model is designed on a known bisphosphonate BPH-629 and used to prepare an enriched compound library that was further docked into UppS conformational ensemble generated by molecular dynamics experiment. The docking results in three anthranilic acid derivatives with promising inhibitory activity against the enzyme
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[2-[3-(octyloxy)benzamido]phenyl]phosphonic acid
-
-
[3-(3,4-dichlorophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl]bis(phosphonic acid)
-
[3-[4-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxypropane-1,1-diyl]bis(phosphonic acid)
-
[4-([1,1'-biphenyl]-4-yl)butane-1,1-diyl]bis(phosphonic acid)
-
[hydroxy([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)methylene]bis(phosphonic acid)
-
[[(9-ethyl-9H-carbazol-3-yl)amino](hydroxy)methylene]bis(phosphonic acid)
-
(2E,6E)-farnesyl thiodiphosphate
-
(2E,6E)-farnesyl diphosphate analogue
(2E,6E)-farnesyl thiodiphosphate
-
substrate analogue
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
-
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
-
-
1,2-Cyclohexanedione
-
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
-
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
-
-
1,4-bis(6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indol-2-yl)benzene
-
1,4-bis(6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indol-2-yl)benzene
-
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
-
-
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
-
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
-
-
2-propanol
-
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
barely inhibits UPPS of Escherichia coli; barely inhibits UPPS of Escherichia coli; i.e. HTS04781. contrary to Helicobacter pylori, HTS04781 is almost not inhibitory in Escherichia coli
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
i.e. HTS04781, crystallization data. The sulfonamide group forms H-bonds with Gly16 and Arg26 and the N atom in the tetracyclic ring is hydrogen bound to the main chain of Met12. Extensive hydrophobic interactions are found between the tetracyclic ring with the surrounding residues including Met12, His30, Gly33 and Val34
4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
-
4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
-
-
BPH-629
-
potent inhibitor
BPH-629
-
bindiing structure in enzyme chain B, overview
Butanedione
-
clomiphene
inhibits the synthesis of undecaprenyl phosphate, antagonizes the activity of targocil
clomiphene
inhibits the synthesis of undecaprenyl phosphate, antagonizes the activity of targocil
EDTA
-
-
farnesyl thiodiphosphate
-
farnesyl thiodiphosphate
-
-
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
MAC-0557874
-
MAC-0588238
-
MAC-0602693
-
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
barely inhibits UPPS of Escherichia coli; i.e. BTB06061
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
i.e. BTB06061, crystallization data. The sulfur atom in the thiazole ring of BTB06061 may form H-bonds with Asn15 and His30 while the SO2 group is hydrogen bound with Met12. The aromatic rings of BTB06061 form hydrophobic interactions with the surrounding hydrophobic residues, including Val34, Leu37, Ala56 and Tyr79
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
weak inhibition
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
-
weak inhibition
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
-
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
-
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
-
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
-
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
-
-
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
i.e. BPH-1358
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
-
i.e. BPH-1358
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
-
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
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N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
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N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
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N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
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Phenylglyoxal
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spirohexaline
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spirohexaline
the molecule shows weak inhibitory activity against catalytically related enzymes such as bacterial octaprenyl pyrophosphate synthase and yeast dehydrodolichyl pyrophosphate synthase, indicating that the compound preferentially inhibits UPP synthase. The inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), via inhibition of the UPP synthase activity. Molecular docking and homology modeling of UPP synthase-spirohexaline complex
targocil
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tetramic acid
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the crystal structure is used for modelling with bound inhibitor tetramic acid
tetramic acid
binding structure, overview
Triton X-100
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C55 is retained in the active site for further elongation, whereas the kcat is increased by 190fold under steady-state condition by 0.1% Triton X-100
Triton X-100
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inhibition at concentration above 1%
Triton X-100
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marked decrease of activity when a small amount of detergent is added, activity gradually increases as further detergent is added, being fully restored when the concentration reaches 2%
viridicatumtoxin
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viridicatumtoxin
originally isolated from Penicillium viridicatum, the molecule shows weak inhibitory activity against catalytically related enzymes such as bacterial octaprenyl pyrophosphate synthase and yeast dehydrodolichyl pyrophosphate synthase, indicating that the compound preferentially inhibits UPP synthase. The inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Molecular modeling strongly suggests that the hydrophobic spirobicyclic ring of viridicatumtoxin interacts with three hydrophobic clefts of the active site in MRSA UPP synthase
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
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[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
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additional information
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Z-isomer ZHIPP, (Z)-3-methyl-3-pentenyl diphosphate, which is not accepted as substrate by the enzyme, exhibited no inhibition on the synthase reaction
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additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase; small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
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additional information
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farnesol (1 mM) lacking the diphosphate does not inhibit the UPPS reaction; no inhibition by farnesol
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additional information
screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
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additional information
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screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
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additional information
antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
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additional information
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a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
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additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
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additional information
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virtual screening of inhibitors from a library of 58635 compounds performed
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additional information
virtual screening of inhibitors from a library of 58635 compounds performed
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additional information
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no inhibition by phosphate
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additional information
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no inhibition by phosphate
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additional information
the inhibitors tested show antimicrobial, cytotoxic, and enzyme inhibitory activities, overview
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additional information
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the inhibitors tested show antimicrobial, cytotoxic, and enzyme inhibitory activities, overview
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additional information
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screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
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additional information
antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
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additional information
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antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
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additional information
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a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
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additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
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additional information
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tetramic acids are selective and potent inhibitors of UPPS
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