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(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
(1R,3R,4R)-1,3,4-trihydroxy-5-(3,5-difluoro)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-carboxylic)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-fluoro)phenylcyclo-hex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-hydroxy)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-nitro)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-trifluoromethyl)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(4-fluoro)phenylcyclo-hex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(4-trifluoromethyl)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(furan-3-yl)phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(pyridine-3-yl)cyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-(thiophen-3-yl)phenyl-cyclohex-5-en-1-carboxylic acid
-
-
(1R,3R,4R)-1,3,4-trihydroxy-5-phenylcyclohex-5-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(1H-1,2,3-triazol-4-yl)cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrothien-3-yl)cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-bromothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-hydroxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(4-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(thien-2-yl)cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-naphthalen-2-ylcyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-phenylcyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-pyridin-3-ylcyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-thiophen-3-ylcyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-phenoxy-prop-(E)-enyl]-cyclohex-2-enecarboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[4-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-3-(1-benzofuran-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(1-benzofuran-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(1-benzothiophen-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(1-benzothiophen-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
(1R,4R,5R)-3-(3,5-difluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(3-carbonitrilethien-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-3-(3-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(4-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(furan-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
(1R,4R,5R)-3-furan-3-yl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4S,5R)-1,3,4,5-tetrahydroxycyclohex-2-ene-1-carboxylate
-
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid
(1R,4S,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
(1S,3R,4R)-1,3,4-trihydroxy-5-cyclohexene-1-carboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
(1S,4R,5R)-3-(3-benzoylphenyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
(2R)-2-methyl-3-dehydroquinic acid
compound is a reversible competive inhibitor of type 1 enzymes and a weak substrate of type 2 enzymes
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
(2S)-2-[5-(2,4-dioxo-1,4-dihydroquinazolin-3(2H)-yl)pentyl]-2-hydroxybutanedioic acid
quinazolinedione derivative that disables the catalytic loop plasticity, compound forces the catalytic loop into an inappropriate arrangement for catalysis by strong interactions with the catalytic tyrosine and by expelling the essential arginine out of the active site
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
(3S,5R,7R,8S)-5,7,8-trihydroxy-1-oxaspiro[2.5]octane-5-carboxylic acid
time-dependent irreversible inhibitor, % inhibition in 30 min at 0.274 mM
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
1,3,4-trihydroxy-5-hydroxyiminocyclohexanecarboxylic acid
1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
1,3,4-trihydroxycyclohexanecarboxylic acid
1,4,5-trihydroxycyclohex-2-enecarboxylic acid
2,5-dichloro-N-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide
-
-
2,5-dichloro-N-(6-methoxy-1,3-benzothiazol-2-yl)benzenesulfonamide
-
-
2-[(4,5,6,7-tetrahydro-1-benzothiophen-3-ylcarbonyl)amino]benzoic acid
-
-
3,4-dihydroxy-5-((3-nitrobenzyl)oxy)benzoic acid
most potent isophthalate inhibitor found
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
3-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]benzoic acid
-
3-[(Z)-[(5Z)-3-ethyl-5-[[4-(2-methoxy-2-oxoethoxy)phenyl]methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
no cytotoxicity up to 100 microM
3-[(Z)-[(5Z)-5-[[4-(benzyloxy)phenyl]methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
no cytotoxicity up to 100 microM
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
4-hydroxy-4-methyl-pent-2-enedioic acid
5-[(3-nitrobenzyl)amino]benzene-1,3-dicarboxylic acid
most potent gallate-based inhibitor found
7-hydroxycoumarin
uncompetitive inhibitor
benzo[b]thiophen-5-yl-3-dehydroquinic acid
citrazinic acid
a planar analogue of the reaction product, complex structure, overview
marein
flavonoid polyketide, mixed type inhibitor, both inhibits DHQase and retards the growth of Enterococcus faecalis
N-tetrazol-5-yl-9-oxo-9H-xanthene-2-sulfonamide
-
rhoifolin
flavonoid glycoside, uncompetitive inhibitor
SDS
-
55 C, irreversible inactivation
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(5-methylbenzo[b]-thiophen-2-yl)methoxycyclohex-2-en-1-carboxylate
-
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(benzo[b]thiophen-2-yl)methoxycyclohex-2-en-1-carboxylate
-
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(thien-2-yl)methoxycyclohex-2-en-1-carboxylate
-
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
-
-
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
-
-
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
-
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
-
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid
competitive inhibitor
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid
competitive inhibitor
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
inhibitor is selective for the type II dehydroquinase over the type I dehydroquinase
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
-
-
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
inhibitor is selective for the type II dehydroquinase over the type I dehydroquinase
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
competitive inhibitor
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
a competitive inhibitor
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
competitive inhibitor
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
inhibitor is selective for the type II dehydroquinase over the type I dehydroquinase
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
-
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
inhibitor is selective for the type II dehydroquinase over the type I dehydroquinase
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
a reversible, competitive inhibitor of DHQ2
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
-
a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
a reversible, competitive inhibitor of DHQ2
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
-
a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
a reversible, competitive inhibitor of DHQ2
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
-
a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
a competitive inhibitor
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
-
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
a competitive inhibitor
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
-
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
-
-
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
-
-
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
-
-
1,3,4-trihydroxy-5-hydroxyiminocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxy-5-hydroxyiminocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxy-5-hydroxyiminocyclohexanecarboxylic acid
-
poor inhibition
1,3,4-trihydroxy-5-hydroxyiminocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
-
poor inhibition
1,3,4-trihydroxy-5-oxocyclohexanecarboxylic acid
-
-
1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
1,3,4-trihydroxycyclohexanecarboxylic acid
-
poor inhibition
1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
-
1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
-
1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
poor inhibition
1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
-
2,3-anhydroquinate
-
2,3-anhydroquinate
mimics the flattened enol/enolate reaction intermediate and serves as an anchor molecule for four of the inhibitors investigated, overview. Structure of MtDHQase in complex with a 2,3-anhydroquinate moiety attached to a biaryl group shows that this group extends to an active-site subpocket inducing significant structural rearrangement
2,3-anhydroquinic acid
-
-
2,3-anhydroquinic acid
-
-
2,3-anhydroquinic acid
-
poor inhibition
2,3-anhydroquinic acid
-
-
3-deoxyquinic acid
-
-
3-deoxyquinic acid
-
poor inhibition
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
-
-
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
-
-
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
competitive inhibitor
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
competitive inhibitor
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
competitive inhibitor
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
-
-
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
-
-
4-hydroxy-4-methyl-pent-2-enedioic acid
-
-
4-hydroxy-4-methyl-pent-2-enedioic acid
-
-
benzo[b]thiophen-5-yl-3-dehydroquinic acid
a reversible, competitive inhibitor of DHQ2
benzo[b]thiophen-5-yl-3-dehydroquinic acid
-
a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication
Cl-
-
-
Cl-
-
no significant effect
diethyl dicarbonate
-
-
guanidine hydrochloride
-
55 C, irreversible inactivation
guanidine hydrochloride
-
-
NaBH4
-
-
NaBH4
-
irreversible inactivation in presence of 3-dehydroquinate
NaBH4
-
irreversible inactivation in presence of 3-dehydroquinate
additional information
binding mechanism of (2R)-2-benzyl-3-dehydroquinic acids, molecular dynamics simulations, overview
-
additional information
-
binding mechanism of (2R)-2-benzyl-3-dehydroquinic acids, molecular dynamics simulations, overview
-
additional information
development of a range of ene-yne-based inhibitors, active site docking study using enzyme structure PDB ID 2WKS, overview
-
additional information
-
inhibitor design and synthesis, binding structure and inhibition mechanism, overview
-
additional information
-
the in silico design, synthesis, and biological evaluation of ten potent type II dehydroquinase inhibitors are described. These compounds contain an anhydroquinate core, incorporated as a mimic of the enolate reaction intermediate. This substructure is attached by a variety of linking units to a terminal phenyl group that binds in an adjacent pocket. Inhibitors are synthesised from (-)-quinic acid using palladium-catalysed Stille and carboamidation chemistry. Several inhibitors exhibited nanomolar inhibition constants
-
additional information
-
nanomolar competitive inhibitors
-
additional information
active-site binding of inhibitors, structure, overview
-
additional information
-
active-site binding of inhibitors, structure, overview
-
additional information
-
binding mechanism of (2R)-2-benzyl-3-dehydroquinic acids, molecular dynamics simulations, overview
-
additional information
-
development of a range of ene-yne-based inhibitors, overview
-
additional information
-
inhibitor design and synthesis, binding structure and inhibition mechanism, overview
-
additional information
RNA interference of NtDHD/SHD-1 strongly inhibits DHD/SHD activity in transgenic tobacco plants
-
additional information
RNA interference of NtDHD/SHD-1 strongly inhibits DHD/SHD activity in transgenic tobacco plants
-
additional information
-
RNA interference of NtDHD/SHD-1 strongly inhibits DHD/SHD activity in transgenic tobacco plants
-
additional information
-
Ki-values for (1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid and (1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid are above 25 mM
-
additional information
-
the in silico design, synthesis, and biological evaluation of ten potent type II dehydroquinase inhibitors are described. These compounds contain an anhydroquinate core, incorporated as a mimic of the enolate reaction intermediate. This substructure is attached by a variety of linking units to a terminal phenyl group that binds in an adjacent pocket. Inhibitors are synthesised from (-)-quinic acid using palladium-catalysed Stille and carboamidation chemistry. Several inhibitors exhibited nanomolar inhibition constants
-
additional information
-
nanomolar competitive inhibitors
-
additional information
development of a range of ene-yne-based inhibitors, active site docking study using enzyme structure PDB ID 1GU1, overview
-
additional information
-
inhibitor design and synthesis, binding structure and inhibition mechanism, overview
-
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0.000026 - 0.00017
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
0.000089 - 0.00025
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
0.00076 - 0.0093
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
0.0017 - 0.02
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
0.000028 - 0.00016
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
0.0001 - 0.0014
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
0.000047 - 0.0026
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
0.0001 - 0.00142
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
0.00009 - 0.00097
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
0.00185 - 0.0215
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
0.000056 - 0.0009
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
0.00009 - 0.00118
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
0.000074 - 0.00097
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
2.44
(1R,3R,4R)-1,3,4-trihydroxy-5-(3,5-difluoro)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
150
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-carboxylic)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
1.5
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-fluoro)phenylcyclo-hex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
95
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-hydroxy)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
0.054
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-nitro)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
2.125
(1R,3R,4R)-1,3,4-trihydroxy-5-(3-trifluoromethyl)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
1.8
(1R,3R,4R)-1,3,4-trihydroxy-5-(4-fluoro)phenylcyclo-hex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
17
(1R,3R,4R)-1,3,4-trihydroxy-5-(4-trifluoromethyl)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
0.83
(1R,3R,4R)-1,3,4-trihydroxy-5-(furan-3-yl)phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
45
(1R,3R,4R)-1,3,4-trihydroxy-5-(pyridine-3-yl)cyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
0.59
(1R,3R,4R)-1,3,4-trihydroxy-5-(thiophen-3-yl)phenyl-cyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
1.5
(1R,3R,4R)-1,3,4-trihydroxy-5-phenylcyclohex-5-en-1-carboxylic acid
-
pH 8.2, 25°C
0.37
(1R,4R,5R)-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
0.0000057 - 0.000225
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
0.063
(1R,4R,5R)-1,4,5-trihydroxy-3-(1H-1,2,3-triazol-4-yl)cyclohex-2-en-1-carboxylic acid
-
0.015 - 0.188
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
0.141
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
0.11
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrothien-3-yl)cyclohex-2-en-1-carboxylic acid
-
0.0046
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-bromothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
0.128
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-hydroxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
0.000054 - 0.0384
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
0.001
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
0.00049
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
0.0068
(1R,4R,5R)-1,4,5-trihydroxy-3-(4-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
0.00054
(1R,4R,5R)-1,4,5-trihydroxy-3-(thien-2-yl)cyclohex-2-en-1-carboxylic acid
-
0.00025 - 0.00059
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
0.0112 - 0.282
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
0.0037
(1R,4R,5R)-1,4,5-trihydroxy-3-naphthalen-2-ylcyclohex-2-ene-1-carboxylic acid
-
0.0074
(1R,4R,5R)-1,4,5-trihydroxy-3-phenylcyclohex-2-ene-1-carboxylic acid
-
0.056
(1R,4R,5R)-1,4,5-trihydroxy-3-pyridin-3-ylcyclohex-2-ene-1-carboxylic acid
-
0.0018
(1R,4R,5R)-1,4,5-trihydroxy-3-thiophen-3-ylcyclohex-2-ene-1-carboxylic acid
-
0.00012
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.00048 - 0.0105
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
0.027 - 0.033
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
0.0145 - 0.0405
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
0.034 - 0.037
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
0.000048 - 0.00033
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
0.000078 - 0.000538
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
0.0000057 - 0.000375
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
0.000073 - 0.001579
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
0.00038
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(phenylsulfanyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.139
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
0.00014
(1R,4R,5R)-1,4,5-trihydroxy-3-[3-phenoxy-prop-(E)-enyl]-cyclohex-2-enecarboxylic acid
recombinant enzyme, pH 7.0, 25°C
0.0084
(1R,4R,5R)-1,4,5-trihydroxy-3-[4-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
0.03 - 3
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.0142
(1R,4R,5R)-3-(1-benzofuran-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.0071
(1R,4R,5R)-3-(1-benzofuran-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.0036
(1R,4R,5R)-3-(1-benzothiophen-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.0081
(1R,4R,5R)-3-(1-benzothiophen-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.025 - 0.105
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
0.0205
(1R,4R,5R)-3-(3,5-difluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.4
(1R,4R,5R)-3-(3-carbonitrilethien-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
larger than 0.400 mM
0.0094
(1R,4R,5R)-3-(3-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.011
(1R,4R,5R)-3-(4-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.001
(1R,4R,5R)-3-(furan-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
0.027 - 0.029
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
0.00485
(1R,4R,5R)-3-furan-3-yl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
0.000029 - 0.000561
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000217 - 0.0022
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.0023
(1R,4S,5R)-1,4,5-trihydroxy-3-[(1E)-3-phenoxyprop-1-en-1-yl]cyclohex-2-ene-1-carboxylic acid
recombinant enzyme, pH 7.0, 25°C
0.7 - 8
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
0.00013
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.01 - 1.5
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
0.015 - 0.5
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
0.6 - 4.5
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
0.7 - 2.5
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
0.011
(1S,4R,5R)-3-(3-benzoylphenyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
recombinant enzyme, pH 7.0, 25°C
0.305
(2R)-2-methyl-3-dehydroquinic acid
pH 7.2, 25°C
0.000032 - 0.00094
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
0.00024 - 0.016
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
0.2 - 0.37
2,3-anhydroquinate
0.01
3,4-dihydroxy-5-((3-nitrobenzyl)oxy)benzoic acid
pH 7.0, 25°C
0.76 - 1.7
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
0.15
3-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]benzoic acid
-
0.00172 - 0.00578
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
0.65 - 1
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
0.47 - 0.99
4-hydroxy-4-methyl-pent-2-enedioic acid
0.0075
5-[(3-nitrobenzyl)amino]benzene-1,3-dicarboxylic acid
pH 7.0, 25°C
0.042
7-hydroxycoumarin
pH 7.5, 25°C
0.0000008
carbaphosphonate
-
-
0.3
citrazinic acid
recombinant enzyme, pH 7.0, 25°C
0.02
N-tetrazol-5-yl-9-oxo-9H-xanthene-2-sulfonamide
-
0.019
rhoifolin
pH 7.5, 25°C
0.00013
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(5-methylbenzo[b]-thiophen-2-yl)methoxycyclohex-2-en-1-carboxylate
in 50 mM Tris-HCl, pH 7, at 25°C
0.000132
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(benzo[b]thiophen-2-yl)methoxycyclohex-2-en-1-carboxylate
in 50 mM Tris-HCl, pH 7, at 25°C
0.00092
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-(thien-2-yl)methoxycyclohex-2-en-1-carboxylate
in 50 mM Tris-HCl, pH 7, at 25°C
0.000166
sodium (1R,4S,5R)-1,4,5-trihydroxy-3-[(benzo[b]thiophen-5-yl)methoxy]cyclohex-2-en-1-carboxylate
in 50 mM Tris-HCl, pH 7, at 25°C
additional information
additional information
-
Ki-values for (1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid and (1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid are above 25 mM
-
0.000026
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00017
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.000089
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00025
(1R,2R,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.00076
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.0093
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.0017
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.02
(1R,2R,4S,5R)-1,4,5-trihydroxy-3-oxo-2-propylcyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.000028
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00016
(1R,2R,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.0001
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris·HCl
0.0014
(1R,2R,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.000047
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.0026
(1R,2R,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.0001
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00142
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methoxybenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.00009
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00097
(1R,2S,4S,5R)-1,4,5-trihydroxy-2-(4-methylbenzyl)-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.00185
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.0215
(1R,2S,4S,5R)-1,4,5-trihydroxy-3-oxo-2-(prop-2-en-1-yl)cyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.000056
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.0009
(1R,2S,4S,5R)-2-(1-benzothiophen-5-yl)-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.00009
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00118
(1R,2S,4S,5R)-2-benzyl-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.000074
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HOAc
0.00097
(1R,2S,4S,5R)-2-[difluoro(pentafluorophenyl)methyl]-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid
pH 7.0, 25°C, 50 mM Tris-HCl
0.0000057
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000039
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000225
(1R,4R,5R)-1,4,5-trihydroxy-3-(1-phenyl-1H-1,2,3-triazol-4-yl)cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.015
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.188
(1R,4R,5R)-1,4,5-trihydroxy-3-(2-hydroxy)ethylcyclohex-2-ene-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.000054
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.0384
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
0.00049
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
in 50 mM Tris-HCl, pH 7, at 25°C
0.00049
(1R,4R,5R)-1,4,5-trihydroxy-3-(3-phenoxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.00025
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.00054
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.00059
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-yl)cyclohex-2-ene-1-carboxylic acid
in 50 mM Tris-HCl, pH 7, at 25°C
0.0112
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.282
(1R,4R,5R)-1,4,5-trihydroxy-3-hydroxymethylcyclohex-2-en-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.00048
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.0105
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.027
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.033
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1R)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.0145
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.0405
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-chloro-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.034
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
at pH 7.0, 25°C, 50 mM Tris-HCl
0.037
(1R,4R,5R)-1,4,5-trihydroxy-3-[(1S)-1-hydroxy-2-phenylethyl]cyclohex-2-en-1-carboxylic acid
-
at pH 7.0, 25°C, 50 mM Tris-HCl
0.000048
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000157
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.00033
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(2-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000078
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.00023
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000538
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.0000057
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000136
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000375
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000073
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000925
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.001579
(1R,4R,5R)-1,4,5-trihydroxy-3-[1-(thiophen-2-ylmethyl)-1H-1,2,3-triazol-4-yl]cyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.03
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
0.06
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
0.2
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
3
(1R,4R,5R)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
-
0.025
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
-
pH 7.0
0.105
(1R,4R,5R)-3-(2-carboxy-vinyl)-1,4,5-trihydroxy-cyclohex-2-enecarboxylic acid
-
pH 7.0
0.027
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
pH 7.0
0.027
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
recombinant enzyme, pH 7.0, 25°C
0.029
(1R,4R,5R)-3-(tert-butylcarbamoyl)-1,4,5-trihydroxycyclohex-2-enecarboxylic acid
-
pH 7.0
0.000029
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000154
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000561
(1R,4R,5R)-3-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.000217
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.002122
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.0022
(1R,4R,5R)-3-[1-(furan-2-ylmethyl)-1H-1,2,3-triazol-4-yl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
pH 7.5, 25°C
0.7
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
-
0.7
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
-
8
(1R,4S,5R)-3,3-difluoro-1,4,5-trihydroxycyclohexane-1-carboxylic acid
-
-
0.01
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
0.015
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
1.5
(1R,4S,5R)-3-fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
-
0.015
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
0.02
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
0.5
(1S,3R,4R)-1,3,4-trihydroxy-5-methylenecyclohexanecarboxylic acid
-
-
0.6
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
1.2
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
1.5
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
4.5
(1S,3R,4R)-1,3,4-trihydroxycyclohexanecarboxylic acid
-
-
0.7
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
2.2
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
2.5
(1S,3R,4R,5E)-1,3,4-trihydroxy-5-(methylimino)cyclohexanecarboxylic acid
-
-
0.000032
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
pH 7.0
0.00094
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
pH 7.0
0.00094
(3R,5R,6R)-3,5,6-trihydroxycyclohex-1-ene-1,3-dicarboxylic acid
-
pH not specified in the publication, temperature not specified in the publication
0.00024
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
-
pH 7.0
0.016
(3R,5R,6R)-3-carbamoyl-3,5,6-trihydroxycyclohex-1-enecarboxylic acid
-
pH 7.0
0.2
2,3-anhydroquinate
recombinant enzyme, pH 7.0, 25°C
0.37
2,3-anhydroquinate
-
0.76
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
-
pH 7.0
1.7
3-hydroxy-cyclohex-1-ene-1,3-dicarboxylic acid
-
pH 7.0
0.00172
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
pH 7.5, 25°C
0.003126
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
pH 7.5, 25°C
0.00578
3-[4-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]-1H-1,2,3-triazol-1-yl]benzoic acid
-
pH 7.5, 25°C
0.65
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
-
pH 7.0
1
4-hydroxy-2-hydroxymethyl-4-methyl-pent-2-enedioic acid
-
pH 7.0
0.47
4-hydroxy-4-methyl-pent-2-enedioic acid
-
pH 7.0
0.99
4-hydroxy-4-methyl-pent-2-enedioic acid
-
pH 7.0
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.000028 - 0.000356
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000171 - 0.002194
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.000168 - 0.001203
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.0000071 - 0.000316
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
0.0000022 - 0.000133
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
0.0000069 - 0.000108
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
0.0000075 - 0.000126
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000012 - 0.000548
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
0.000035
(1R,4S,5R)-1,4,5-trihydroxy-3-(naphthalen-2-ylmethoxy)cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
at pH 7.0 and 25°C
0.000042
(1R,4S,5R)-1,4,5-trihydroxy-3-[(5-methyl-1-benzothiophen-2-yl)methoxy]cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
at pH 7.0 and 25°C
0.000028
(1R,4S,5R)-3-(1-benzothiophen-2-ylmethoxy)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
at pH 7.0 and 25°C
0.000026 - 0.00017
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
0.000089 - 0.00025
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
0.000047 - 0.0026
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
0.00000084 - 0.0006
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.000052 - 0.00126
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.000069 - 0.00032
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.0000011 - 0.00108
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.000022 - 0.000122
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.00086 - 0.038
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.00019 - 0.0034
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.0004 - 0.00315
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.000093 - 0.00035
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.0003 - 0.034
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
0.034
2,5-dichloro-N-(4-phenyl-1,3-thiazol-2-yl)benzenesulfonamide
Clostridioides difficile
-
in 50 mM HEPES, pH 7.5, at 22°C
0.035
2,5-dichloro-N-(6-methoxy-1,3-benzothiazol-2-yl)benzenesulfonamide
Clostridioides difficile
-
in 50 mM HEPES, pH 7.5, at 22°C
0.031
2-[(4,5,6,7-tetrahydro-1-benzothiophen-3-ylcarbonyl)amino]benzoic acid
Clostridioides difficile
-
in 50 mM HEPES, pH 7.5, at 22°C
0.0171
3-[(Z)-[(5Z)-3-ethyl-5-[[4-(2-methoxy-2-oxoethoxy)phenyl]methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
Mycobacterium tuberculosis
pH 7.0, 25°C
0.0315
3-[(Z)-[(5Z)-5-[[4-(benzyloxy)phenyl]methylidene]-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino]benzoic acid
Mycobacterium tuberculosis
pH 7.0, 25°C
0.000028 - 0.00016
benzo[b]thiophen-5-yl-3-dehydroquinic acid
0.061
HTS 11955
Helicobacter pylori
-
-
0.0845
RH00573
Helicobacter pylori
-
-
0.000028
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000253
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.000356
(1R,4R,5R)-1,4,5-trihydroxy-3-(phenylethynyl)cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000171
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000712
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.002194
(1R,4R,5R)-1,4,5-trihydroxy-3-(pyridin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000168
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000885
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.001203
(1R,4R,5R)-1,4,5-trihydroxy-3-(quinolin-3-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.0000071
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000187
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000316
(1R,4R,5R)-1,4,5-trihydroxy-3-(thiophen-2-ylethynyl)cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.0000022
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000098
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.000133
(1R,4R,5R)-1,4,5-trihydroxy-3-[(3-nitrophenyl)ethynyl]cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0000069
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000103
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.000108
(1R,4R,5R)-1,4,5-trihydroxy-3-[[3-(trifluoromethyl)phenyl]ethynyl]cyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0000075
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000094
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.000126
(1R,4R,5R)-3-(1,3-benzothiazol-2-ylethynyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000012
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Streptomyces coelicolor
pH 7.5, 25°C
0.000106
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Helicobacter pylori
pH 7.5, 25°C
0.000548
(1R,4R,5R)-3-[(4-fluorophenyl)ethynyl]-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000026
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.00017
(2R)-2-p-methoxybenzyl-3-dehydroquinic acid
Helicobacter pylori
pH and temperature not specified in the publication
0.000089
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.00025
(2R)-2-p-methylbenzyl-3-dehydroquinic acid
Helicobacter pylori
pH and temperature not specified in the publication
0.000047
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0026
(2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
Helicobacter pylori
pH and temperature not specified in the publication
0.00000084
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.00009
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0006
(4R,6R,7S)-2-(1-cyclopropylethyl)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.000052
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.00081
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.00126
(4R,6R,7S)-2-ethenyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.000069
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.00032
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.00032
(4R,6R,7S)-2-ethyl-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.0000011
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.00011
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.00108
(4R,6R,7S)-2-[(1E)-2-cyclopropylprop-1-en-1-yl]-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.000022
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.000049
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.000122
(4R,6R,7S)-4,6,7-trihydroxy-2-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.00086
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0018
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.038
(4R,6R,7S)-4,6,7-trihydroxy-2-(prop-2-en-1-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.00019
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0019
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.0034
(4R,6R,7S)-4,6,7-trihydroxy-2-(propan-2-yl)-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.0004
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0016
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.00315
(4R,6R,7S)-4,6,7-trihydroxy-2-methyl-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.000093
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.000097
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.00035
(4R,6R,7S)-4,6,7-trihydroxy-2-[(1Z)-prop-1-en-1-yl]-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.0003
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Mycobacterium tuberculosis
-
pH 7.5, 25°C
0.0097
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Streptomyces coelicolor
-
pH 7.5, 25°C
0.034
(4R,6R,7S)-4,6,7-trihydroxy-4,5,6,7-tetrahydro-1-benzothiophene-4-carboxylic acid
Helicobacter pylori
-
pH 7.5, 25°C
0.000028
benzo[b]thiophen-5-yl-3-dehydroquinic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.00016
benzo[b]thiophen-5-yl-3-dehydroquinic acid
Helicobacter pylori
pH and temperature not specified in the publication
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1972
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1978
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Some properties of the initial four enzymes involved in shikimic acid biosynthesis in tea plant
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1979
Camellia sinensis
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Saccharomyces cerevisiae, Meyerozyma guilliermondii, Wickerhamomyces anomalus, Cyberlindnera jadinii, Cyberlindnera fabianii, Ogataea henricii, Lodderomyces elongisporus, Neurospora crassa, Rhodotorula sphaerocarpa, Rhodotorula toruloides, Rhodotorula mucilaginosa, Saccharomycopsis lipolytica
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Cloning the Bacillus 168 aroC gene encoding dehydroquinase
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32
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1984
Bacillus subtilis, Bacillus subtilis 168
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3-Dehydroquinate dehydratase from Escherichia coli
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Escherichia coli, Escherichia coli AB2848/pKD201
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Subcellular localization of the common shikimate-pathway enzymes in Pisum sativum L.
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Salmonella enterica subsp. enterica serovar Typhi
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Streptomyces coelicolor
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Helicobacter pylori, Salmonella enterica subsp. enterica serovar Typhi, Streptomyces coelicolor, Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis H37Rv (P9WPX7)
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Crystallization and preliminary X-ray crystallographic analysis of type II dehydroquinase from Helicobacter pylori
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Comparison of different crystal forms of 3-dehydroquinase from Salmonella typhi and its implication for the enzyme activity
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Structural study of the type II 3-dehydroquinate dehydratase from Actinobacillus pleuropneumoniae
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1
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Streptomyces coelicolor
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10
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2002
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Inhibitors of types I and II dehydroquinase
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4
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2004
Aspergillus nidulans, Mycobacterium tuberculosis, Salmonella enterica subsp. enterica serovar Typhimurium, Streptomyces coelicolor
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(1R,4S,5R)-3-Fluoro-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid: the fluoro analogue of the enolate intermediate in the reaction catalyzed by type II dehydroquinases
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2
1592-1596
2004
Salmonella enterica subsp. enterica serovar Typhi, Streptomyces coelicolor (P15474), Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis H37Rv (P9WPX7)
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56
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2004
Staphylococcus aureus
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Stewart, K.A.; Robinson, D.A.; Lapthorn, A.J.
Type II dehydroquinase: molecular replacement with many copies
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64
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2008
Helicobacter pylori, Streptomyces coelicolor (P15474)
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Singh, S.A.; Christendat, D.
Structure of Arabidopsis dehydroquinate dehydratase-shikimate dehydrogenase and implications for metabolic channeling in the shikimate pathway
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45
7787-7796
2006
Arabidopsis thaliana (Q9SQT8)
brenda
Toscano, M.D.; Payne, R.J.; Chiba, A.; Kerbarh, O.; Abell, C.
Nanomolar inhibition of type II dehydroquinase based on the enolate reaction mechanism
ChemMedChem
2
101-112
2007
Mycobacterium tuberculosis, Salmonella enterica subsp. enterica serovar Typhi, Streptomyces coelicolor
brenda
Payne, R.J.; Peyrot, F.; Kerbarh, O.; Abell, A.D.; Abell, C.
Rational design, synthesis, and evaluation of nanomolar type II dehydroquinase inhibitors
ChemMedChem
2
1015-1029
2007
Mycobacterium tuberculosis, Streptomyces coelicolor
brenda
Prazeres, V.F.; Sanchez-Sixto, C.; Castedo, L.; Lamb, H.; Hawkins, A.R.; Riboldi-Tunnicliffe, A.; Coggins, J.R.; Lapthorn, A.J.; Gonzalez-Bello, C.
Nanomolar competitive inhibitors of Mycobacterium tuberculosis and Streptomyces coelicolor type II dehydroquinase
ChemMedChem
2
194-207
2007
Mycobacterium tuberculosis, Streptomyces coelicolor
brenda
Ding, L.; Hofius, D.; Hajirezaei, M.R.; Fernie, A.R.; Boernke, F.; Sonnewald, U.
Functional analysis of the essential bifunctional tobacco enzyme 3-dehydroquinate dehydratase/shikimate dehydrogenase in transgenic tobacco plants
J. Exp. Bot.
58
2053-2067
2007
Nicotiana tabacum (Q6PUF9), Nicotiana tabacum (Q6PUG0), Nicotiana tabacum
brenda
Smith, N.N.; Gallagher, D.T.
Structure and lability of archaeal dehydroquinase
Acta Crystallogr. Sect. F
64
886-892
2008
Archaeoglobus fulgidus (O30011), Archaeoglobus fulgidus
brenda
Liu, J.S.; Cheng, W.C.; Wang, H.J.; Chen, Y.C.; Wang, W.C.
Structure-based inhibitor discovery of Helicobacter pylori dehydroquinate synthase
Biochem. Biophys. Res. Commun.
373
1-7
2008
Helicobacter pylori
brenda
Adachi, O.; Ano, Y.; Toyama, H.; Matsushita, K.
A novel 3-dehydroquinate dehydratase catalyzing extracellular formation of 3-dehydroshikimate by oxidative fermentation of Gluconobacter oxydans IFO 3244
Biosci. Biotechnol. Biochem.
72
1475-1482
2008
Gluconobacter oxydans, Gluconobacter oxydans IFO 3244
brenda
Sanchez-Sixto, C.; Prazeres, V.F.; Castedo, L.; Suh, S.W.; Lamb, H.; Hawkins, A.R.; Canada, F.J.; Jimenez-Barbero, J.; Gonzalez-Bello, C.
Competitive inhibitors of Helicobacter pylori type II dehydroquinase: synthesis, biological evaluation, and NMR studies
ChemMedChem
3
756-770
2008
Helicobacter pylori (Q48255), Helicobacter pylori
brenda
Han, J.; Lee, K.; Yoon, M.; Kang, S.; Kim, G.
Cold stress regulation of a bi-functional 3-dehydroquinate dehydratase/shikimate dehydrogenase (DHQ/SDH)-like gene in the freshwater green alga Spirogyra varians
Botanica Marina
52
178-185
2009
Spirogyra varians
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brenda
Prazeres, V.; Castedo, L.; Lamb, H.; Hawkins, A.; Gonzlez-Bello, C.
2-Substituted-3-dehydroquinic acids as potent competitive inhibitors of type II dehydroquinase
ChemMedChem
4
1980-1984
2009
Mycobacterium tuberculosis (P9WPX7), Helicobacter pylori (Q48255), Mycobacterium tuberculosis H37Rv (P9WPX7)
brenda
Blomberg, L.; Mangold, M.; Mitchell, J.; Blumberger, J.
Theoretical study of the reaction mechanism of Streptomyces coelicolor type II dehydroquinase
J. Chem. Theory Comput.
5
1284-1294
2009
Streptomyces coelicolor (P15474), Streptomyces coelicolor
brenda
Prazeres, V.F.; Tizon, L.; Otero, J.M.; Guardado-Calvo, P.; Llamas-Saiz, A.L.; van Raaij, M.J.; Castedo, L.; Lamb, H.; Hawkins, A.R.; Gonzalez-Bello, C.
Synthesis and biological evaluation of new nanomolar competitive inhibitors of Helicobacter pylori type II dehydroquinase. Structural details of the role of the aromatic moieties with essential residues
J. Med. Chem.
53
191-200
2010
Helicobacter pylori (Q48255), Helicobacter pylori
brenda
Dias, M.V.; Snee, W.C.; Bromfield, K.M.; Payne, R.J.; Palaninathan, S.K.; Ciulli, A.; Howard, N.I.; Abell, C.; Sacchettini, J.C.; Blundell, T.L.
Structural investigation of inhibitor designs targeting 3-dehydroquinate dehydratase from the shikimate pathway of Mycobacterium tuberculosis
Biochem. J.
436
729-739
2011
Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WPX7)
brenda
Light, S.H.; Minasov, G.; Shuvalova, L.; Peterson, S.N.; Caffrey, M.; Anderson, W.F.; Lavie, A.
A conserved surface loop in type I dehydroquinate dehydratases positions an active site arginine and functions in substrate binding
Biochemistry
50
2357-2363
2011
no activity in Homo sapiens, Salmonella enterica (P58687), Salmonella enterica
brenda
Shinagawa, E.; Adachi, O.; Ano, Y.; Yakushi, T.; Matsushita, K.
Purification and characterization of membrane-bound 3-dehydroshikimate dehydratase from Gluconobacter oxydans IFO 3244, a new enzyme catalyzing extracellular protocatechuate formation
Biosci. Biotechnol. Biochem.
74
1084-1088
2010
Gluconobacter oxydans, Gluconobacter oxydans IFO 3244
brenda
Peon, A.; Otero, J.M.; Tizon, L.; Prazeres, V.F.; Llamas-Saiz, A.L.; Fox, G.C.; van Raaij, M.J.; Lamb, H.; Hawkins, A.R.; Gago, F.; Castedo, L.; Gonzalez-Bello, C.
Understanding the key factors that control the inhibition of type II dehydroquinase by (2R)-2-benzyl-3-dehydroquinic acids
ChemMedChem
5
1726-1733
2010
Mycobacterium tuberculosis, Helicobacter pylori (Q48255), Helicobacter pylori
brenda
Tran, A.; Cergol, K.; West, N.; Randall, E.; Britton, W.; Bokhari, S.; Ibrahim, M.; Lapthorn, A.; Payne, R.
Synthesis and evaluation of potent ene-yne inhibitors of type II dehydroquinases as tuberculosis drug leads
ChemMedChem
6
262-265
2011
Mycobacterium tuberculosis, Streptomyces coelicolor (P15474), Helicobacter pylori (Q48255)
brenda
Paz, S.; Tizon, L.; Otero, J.; Llamas-Saiz, A.; Fox, G.; Van Raaij, M.; Lamb, H.; Hawkins, A.; Lapthorn, A.; Castedo, L.; Gonzalez-Bello, C.
Tetrahydrobenzothiophene derivatives: conformationally restricted inhibitors of type II dehydroquinase
ChemMedChem
6
266-272
2011
Helicobacter pylori, Mycobacterium tuberculosis, Streptomyces coelicolor
brenda
Light, S.H.; Minasov, G.; Shuvalova, L.; Duban, M.E.; Caffrey, M.; Anderson, W.F.; Lavie, A.
Insights into the mechanism of type I dehydroquinate dehydratases from structures of reaction intermediates
J. Biol. Chem.
286
3531-3539
2011
Clostridioides difficile, Salmonella enterica (P58687), Salmonella enterica, Clostridioides difficile 630, Salmonella enterica LT2 (P58687)
brenda
Tran, A.; Cergol, K.; Britton, W.; Imran Bokhari, S.; Ibrahim, M.; Lapthorn, A.; Payne, R.
Rapid assembly of potent type II dehydroquinase inhibitors via 'click' chemistry
MedChemComm
1
271-275
2010
Helicobacter pylori, Mycobacterium tuberculosis, Streptomyces coelicolor
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brenda
Nishikura-Imamura, S.; Matsutani, M.; Insomphun, C.; Vangnai, A.S.; Toyama, H.; Yakushi, T.; Abe, T.; Adachi, O.; Matsushita, K.
Overexpression of a type II 3-dehydroquinate dehydratase enhances the biotransformation of quinate to 3-dehydroshikimate in Gluconobacter oxydans
Appl. Microbiol. Biotechnol.
98
2955-2963
2014
Gluconobacter oxydans (W6JLW3), Gluconobacter oxydans, Gluconobacter oxydans NBRC3244 (W6JLW3)
brenda
Devi, A.S.; Ebihara, A.; Kuramitsu, S.; Yokoyama, S.; Kumarevel, T.; Ponnuraj, K.
Crystal structure of type I 3-dehydroquinate dehydratase of Aquifex aeolicus suggests closing of active site flap is not essential for enzyme action
Biochem. Biophys. Res. Commun.
432
350-354
2013
Aquifex aeolicus
brenda
Coderch, C.; Lence, E.; Peon, A.; Lamb, H.; Hawkins, A.R.; Gago, F.; Gonzalez-Bello, C.
Mechanistic insight into the reaction catalysed by bacterial type II dehydroquinases
Biochem. J.
458
547-557
2014
Helicobacter pylori, Mycobacterium tuberculosis
brenda
Light, S.H.; Antanasijevic, A.; Krishna, S.N.; Caffrey, M.; Anderson, W.F.; Lavie, A.
Crystal structures of type I dehydroquinate dehydratase in complex with quinate and shikimate suggest a novel mechanism of Schiff base formation
Biochemistry
53
872-880
2014
Salmonella enterica (P58687), Salmonella enterica
brenda
Blanco, B.; Sedes, A.; Peon, A.; Otero, J.M.; van Raaij, M.J.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
Exploring the water-binding pocket of the type II dehydroquinase enzyme in the structure-based design of inhibitors
J. Med. Chem.
57
3494-3510
2014
Helicobacter pylori, Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis
brenda
Yao, Y.; Li, Z.S.
New insights into the mechanism of the Schiff base hydrolysis catalyzed by type I dehydroquinate dehydratase from S. enterica: a theoretical study
Org. Biomol. Chem.
10
7037-7044
2012
Salmonella enterica
brenda
Ratia, K.; Light, S.H.; Antanasijevic, A.; Anderson, W.F.; Caffrey, M.; Lavie, A.
Discovery of selective inhibitors of the Clostridium difficile dehydroquinate dehydratase
PLoS ONE
9
e89356
2014
Clostridioides difficile
brenda
Light, S.H.; Anderson, W.F.; Lavie, A.
Reassessing the type I dehydroquinate dehydratase catalytic triad: kinetic and structural studies of Glu86 mutants
Protein Sci.
22
418-424
2013
Salmonella enterica (P58687), Salmonella enterica
brenda
Reiling, S.; Kelleher, A.; Matsumoto, M.; Robinson, G.; Asojo, O.
Structure of type II dehydroquinase from Pseudomonas aeruginosa
Acta Crystallogr. Sect. F
70
1485-1491
2014
Pseudomonas aeruginosa (O30557), Pseudomonas aeruginosa, Pseudomonas aeruginosa DSM (O30557)
brenda
Liu, C.; Liu, Y.; Sun, Q.; Jiang, C.; Liu, S.
Unraveling the kinetic diversity of microbial 3-dehydroquinate dehydratases of shikimate pathway
AMB Express
5
007
2015
Acetivibrio clariflavus (G8M0G7), Acetivibrio clariflavus DSM 19732 (G8M0G7), Alcanivorax borkumensis (Q0VMZ2), Alcanivorax borkumensis SK-2 (Q0VMZ2), Alicyclobacillus acidocaldarius (B7DR33), Alicyclobacillus acidocaldarius LAA1 (B7DR33), Arthrobacter crystallopoietes (N1V364), Arthrobacter crystallopoietes BAB-32 (N1V364), Bacillus subtilis (P54517), Bacillus subtilis 168 (P54517), Butyrivibrio crossotus (D4S0D1), Butyrivibrio crossotus DSM 2876 (D4S0D1), Citrobacter koseri (A8AQF2), Citrobacter koseri ATCC BAA-895 (A8AQF2), Corynebacterium glutamicum (O52377), Corynebacterium glutamicum, Corynebacterium glutamicum DSM 20300 (O52377), Escherichia coli (P05194), Escherichia coli, Geobacillus sp. Y4.1MC1, Gluconobacter oxydans (WP_011252021), Gluconobacter oxydans 621-H (WP_011252021), Halanaerobium hydrogeniformans (E4RLB7), Klebsiella aerogenes (A0A0H3FM50), Klebsiella aerogenes DSM 30053 (A0A0H3FM50), Klebsiella pneumoniae (EMH96211.1), Klebsiella pneumoniae RYC492 (EMH96211.1), Lancefieldella rimae (B9CK59), Lancefieldella rimae ATCC 49626 (B9CK59), Micromonospora lupini (I0L192), Micromonospora lupini Lupac 08 (I0L192), Mycobacterium tuberculosis (WP_003413001), Mycobacterium tuberculosis KZN 1435 (WP_003413001), Natranaerobius thermophilus (B2A551), Natranaerobius thermophilus DSM 18059 (B2A551), Pseudomonas putida (Q88IJ6), Pseudomonas putida DSM 6125 (Q88IJ6), Psychrobacter sp. PRwf-1 (A5WDH9), Psychromonas ingrahamii (A1SZA3), Psychromonas ingrahamii 37 (A1SZA3), Ruminococcus champanellensis (D4LCT8), Ruminococcus champanellensis DSM 18848 (D4LCT8), Streptomyces acidiscabies (A0A124C1Y7), Thermodesulfobium narugense (M1E6S9), Thermodesulfobium narugense DSM 14796 (M1E6S9), Thermomonospora curvata (D1A7X0), Thermomonospora curvata DSM 43183 (D1A7X0), Xylella fastidiosa (Q9PH97), Xylella fastidiosa 9a5c (Q9PH97)
brenda
Maneiro, M.; Peon, A.; Lence, E.; Otero, J.M.; Van Raaij, M.J.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
Insights into substrate binding and catalysis in bacterial type I dehydroquinase
Biochem. J.
462
415-424
2014
Mycobacterium tuberculosis, Salmonella enterica subsp. enterica serovar Typhi (P24670), Salmonella enterica subsp. enterica serovar Typhi
brenda
de Avila, M.B.; de Azevedo, W.F.
Development of machine learning models to predict inhibition of 3-dehydroquinate dehydratase
Chem. Biol. Drug Des.
92
1468-1474
2018
Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis H37Rv (P9WPX7)
brenda
Howard, N.I.; Dias, M.V.; Peyrot, F.; Chen, L.; Schmidt, M.F.; Blundell, T.L.; Abell, C.
Design and structural analysis of aromatic inhibitors of type II dehydroquinase from Mycobacterium tuberculosis
ChemMedChem
10
116-133
2015
Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis, Mycobacterium tuberculosis ATCC 25618 (P9WPX7)
brenda
Peon, A.; Robles, A.; Blanco, B.; Convertino, M.; Thompson, P.; Hawkins, A.R.; Caflisch, A.; Gonzalez-Bello, C.
Reducing the flexibility of type II dehydroquinase for inhibition a fragment-based approach and molecular dynamics study
ChemMedChem
12
1512-1524
2017
Helicobacter pylori (Q48255), Helicobacter pylori, Helicobacter pylori 26695 (Q48255)
brenda
Iqbal, N.; Kumar, M.; Sharma, P.; Yadav, S.P.; Kaur, P.; Sharma, S.; Singh, T.P.
Binding studies and structure determination of the recombinantly produced type-II 3-dehydroquinate dehydratase from Acinetobacter baumannii
Int. J. Biol. Macromol.
94
459-465
2017
Acinetobacter baumannii (A3M692), Acinetobacter baumannii, Acinetobacter baumannii ATCC 17978 (A3M692)
brenda
Petersen, G.O.; Saxena, S.; Renuka, J.; Soni, V.; Yogeeswari, P.; Santos, D.S.; Bizarro, C.V.; Sriram, D.
Structure-based virtual screening as a tool for the identification of novel inhibitors against Mycobacterium tuberculosis 3-dehydroquinate dehydratase
J. Mol. Graph. Model.
60
124-131
2015
Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv (P9WPX7)
brenda
Tizon, L.; Maneiro, M.; Peon, A.; Otero, J.M.; Lence, E.; Poza, S.; van Raaij, M.J.; Thompson, P.; Hawkins, A.R.; Gonzalez-Bello, C.
Irreversible covalent modification of type I dehydroquinase with a stable Schiff base
Org. Biomol. Chem.
13
706-716
2015
Salmonella enterica subsp. enterica serovar Typhi (P24670), Salmonella enterica subsp. enterica serovar Typhi
brenda
Lence, E.; van der Kamp, M.W.; Gonzalez-Bello, C.; Mulholland, A.J.
QM/MM simulations identify the determinants of catalytic activity differences between type II dehydroquinase enzymes
Org. Biomol. Chem.
16
4443-4455
2018
Mycobacterium tuberculosis (P9WPX7), Mycobacterium tuberculosis, Helicobacter pylori (Q48255), Helicobacter pylori, Helicobacter pylori ATCC 700392 (Q48255), Mycobacterium tuberculosis H37Rv (P9WPX7)
brenda
Cheung, V.W.; Xue, B.; Hernandez-Valladares, M.; Go, M.K.; Tung, A.; Aguda, A.H.; Robinson, R.C.; Yew, W.S.
Identification of polyketide inhibitors targeting 3-dehydroquinate dehydratase in the shikimate pathway of Enterococcus faecalis
PLoS ONE
9
e103598
2014
Enterococcus faecalis (P36923), Enterococcus faecalis, Enterococcus faecalis ATCC 700802 (P36923)
brenda
Tahara, K.; Nishiguchi, M.; Funke, E.; Miyazawa, S.I.; Miyama, T.; Milkowski, C.
Dehydroquinate dehydratase/shikimate dehydrogenases involved in gallate biosynthesis of the aluminum-tolerant tree species Eucalyptus camaldulensis
Planta
253
3
2020
Eucalyptus camaldulensis (A0A5H2WZU5), Eucalyptus camaldulensis (A0A5H2X4C4), Eucalyptus camaldulensis
brenda