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4.2.1.10: 3-dehydroquinate dehydratase

This is an abbreviated version!
For detailed information about 3-dehydroquinate dehydratase, go to the full flat file.

Word Map on EC 4.2.1.10

Reaction

3-dehydroquinate
=
3-dehydroshikimate
 +
H2O

Synonyms

3-dehydroquinase, 3-dehydroquinate dehydratase, 3-dehydroquinate dehydratase /shikimate dehydrogenase isoform 1, 3-dehydroquinate dehydratase /shikimate dehydrogenase isoform 2, 3-dehydroquinate dehydratase/shikimate dehydrogenase, 3-DHQase, 5-dehydroquinase, 5-dehydroquinate dehydratase, 5-dehydroquinate hydro-lyase, AfDQ, aroD, AroQ, bifunctional 3-dehydroquinate dehydratase/shikimate dehydrogenase, chloroplast, dehydratase, 3-dehydroquinate, dehydroquinase, dehydroquinate dehydratase, dehydroquinate dehydratase-shikimate dehydrogenase, dehydroquinate synthase, DHD/SHD, DHQ synthase, DHQ-SDH, DHQ-SDH protein, DHQ/SDH, DHQ1, DHQ2, DHQase, DHQase I, DHQase-SORase, DHQD, DHQS, DQD, EC 4.2.1.10, EcDQD/SDH1, EcDQD/SDH2, mDQD, membrane-bound 3-dehydroquinate dehydratase, More, MtDHQase, NtDHD/SHD-1, NtDHD/SHD-2, pDQD, sDQD, SVCR3, type I 3-dehydroquinate dehydratase, Type I dehydroquinase, type I dehydroquinate dehydratase, Type I DHQase, type I DHQD, type II 3-dehydroquinate dehydratase, Type II dehydroquinase, Type II DHQase

ECTree

     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.1 Hydro-lyases
                4.2.1.10 3-dehydroquinate dehydratase

Inhibitors

Inhibitors on EC 4.2.1.10 - 3-dehydroquinate dehydratase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
2,3-anhydroquinate
2,3-anhydroquinic 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-deoxyquinic acid
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
acetate
-
-
benzo[b]thiophen-5-yl-3-dehydroquinic acid
carbaphosphonate
-
-
citrazinic acid
a planar analogue of the reaction product, complex structure, overview
Cu2+
-
partial
D-(+)-tartrate
-
-
diethyl dicarbonate
Fe2+
-
partial
guanidine hydrochloride
HTS 11955
-
-
hydroxylamine
-
partial
iodoacetamide
-
partial
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
-
NaBH4
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
-
succinate
-
-
Zn2+
-
partial
additional information
-