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2.7.1.71: shikimate kinase

This is an abbreviated version!
For detailed information about shikimate kinase, go to the full flat file.

Word Map on EC 2.7.1.71

Reaction

ATP
+
shikimate
=
ADP
 +
3-phosphoshikimate

Synonyms

adenosine triphosphate: shikimate-3-phosphotransferase, AroK, AroL, AtSK1, AtSK2, kinase (phosphorylating), shikimate, kinase, shikimate (phosphorylating), MtSK, OsSK1, OsSK2, OsSK3, Rv2539c, shikimate kinase II, shikimate kinase-like 1, SK I, SK II, SK1, SK2, SKI, SKII, SKL1, type I shikimate kinase, aroK-encoded, type II shikimate kinase

ECTree

     2 Transferases
         2.7 Transferring phosphorus-containing groups
             2.7.1 Phosphotransferases with an alcohol group as acceptor
                2.7.1.71 shikimate kinase

Inhibitors

Inhibitors on EC 2.7.1.71 - shikimate kinase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-4-epi-shikimic acid
-
(-)-4-epi-shikimic acid
-
(1R,4R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
(1R,4S,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
(1R,6S,10S)-4-benzyloxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-4-butyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-4-cyclopropylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-4-ethoxymethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-4-ethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-4-hydroxylmethyl-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]dec-7-ene-8-carboxylic acid
(1R,6S,10S)-6,10-dihydroxy-2-oxabicyclo[4.3.1]deca-4,7-diene-8-carboxylic acid
(1R,6S,10S)-6,10-dihydroxy-4-methyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(1R,6S,10S)-6,10-dihydroxy-4-propyl-2-oxabicyclo[4.3.1]deca-4(Z),7-diene-8-carboxylic acid
(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]prop-2-enenitrile
-
uncompetitive inhibition towards shikimate and competitive inhibition towards ATP
(2E)-3-phenyl-N-[5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,4-oxadiazol-2-yl]prop-2-enamide
-
-
(2E)-N-(3-acetylphenyl)-3-(4-nitrophenyl)prop-2-enamide
-
non-competitive inhibition towards shikimate and competitive inhibition towards ATP
(2E,5Z)-5-[4-(dimethylamino)benzylidene]-2-(2-oxo-2-phenylethylidene)-1,3-thiazolidin-4-one
-
uncompetitive inhibition towards shikimate and competitive inhibition towards ATP
(2R)-N-[3-chloro-4-(methylsulfonyl)benzyl]-2-hydroxy-2-(1-methyl-1H-pyrazol-4-yl)ethanamide
-
-
(3aR,6R,7R,7aS)-6,7-dihydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxole-4-carboxylic acid
-
weak competitive reversible inhibitor
(3R,4R,5R)-3,4-dihydroxy-5-(3-methoxybenzyloxy)cyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3,4-dihydroxy-5-(3-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3,4-dihydroxy-5-(4-methylbenzyloxy)cyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3,4-dihydroxy-5-(naphthalen-2-ylmethoxy)cyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3,4-dihydroxy-5-(naphthyl-2-yl)methoxycyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3,4-dihydroxy-5-[(3-nitrobenzyl)oxy]cyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-3-amino-4,5-dihydroxycyclohex-1-ene-1-carboxylic acid
-
reversible competitive inhibitor
(3R,4R,5R)-5-(1-benzothiophen-5-ylmethoxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-5-(3-fluorobenzyloxy)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-5-(benzo[b]thiophen-5-yl)methoxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4R,5R)-5-benzyloxy-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4R,5R,6R)-3,4,5,6-tetrahydroxycyclohex-1-ene-1-carboxylic acid
-
weak competitive reversible inhibitor
(3R,4S)-5-(1-benzothiophen-5-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
-
-
(3R,4S,5R)-5-(4-benzyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4S,5R)-5-(4-phenoxymethyl-1H-1,2,3-triazol-1-yl)-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
(3R,4S,5R)-5-bis(3-bromo-1H-indol-5-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylic acid
(3S)-3-aminoshikimic acid
(3S,4R,5R)-3-amino-4,5-dihydroxycyclohex-1-ene-1-carboxylic acid
-
reversible competitive inhibitor
(3S,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
-
-
(4R,7S,8aS)-4-[3-(morpholin-4-yl)-3-oxopropyl]-7-[[4-(trifluoromethoxy)benzyl]amino]hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one
-
-
(4R,7S,8aS)-4-[3-oxo-3-(piperidin-1-yl)propyl]-7-[[4-(trifluoromethoxy)benzyl]amino]hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one
-
-
(NH4)2SO4
-
5 mM, 29% inhibition
1-(2,4-dinitrophenyl)-5-[[(4-fluorophenyl)acetyl]amino]-N-methyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.1 mg/ml
1-(2,4-dinitrophenyl)-N-methyl-5-([[4-(trifluoromethyl)phenyl]acetyl]amino)-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
1-(2,4-dinitrophenyl)-N-methyl-5-[[(4-methylphenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
1-(2,4-dinitrophenyl)-N-methyl-5-[[(4-nitrophenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of more than 0.1 mg/ml
1-(4-chloro-2,5-dimethoxyphenyl)-1H-tetrazole-5-thiol
inhibitor identified by structure-based virtual screening, docking simulations
1-(5-methoxy-1H-pyrazol-3-yl)-3-[2-[(methylsulfonyl)methyl]benzyl]urea
-
-
1-[(3-ethyl-2,6-dimethylquinolin-4-yl)sulfanyl]methanediamine
inhibitor identified by structure-based virtual screening, docking simulations
1-[(3S,5S)-5-[3-(1,3-benzodioxol-5-yl)-1,2,4-oxadiazol-5-yl]-1-methylpyrrolidin-3-yl]-3-propan-2-ylurea
-
-
1-[1-(2-hydroxyethyl)-1H-pyrazol-3-yl]-3-[2-[2-(methylsulfanyl)ethyl]phenyl]urea
-
-
2-(3-methyl-5-sulfanyl-4H-1,2,4-triazol-4-yl)-1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)ethanone
2-(3-[[(3-cyanobenzyl)carbamoyl]amino]-1H-pyrazol-1-yl)-N-methylacetamide
-
-
2-([[3-([(3R,4S)-4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]piperidin-3-yl]methyl)-1,2-oxazol-5-yl]methyl]carbamoyl)benzoic acid
-
-
2-[(2Z)-2-(4-nitrobenzylidene)hydrazinyl]-1,3-benzothiazole
-
-
2-[(4-aminophenyl)amino]-3-(piperidin-1-yl)naphthalene-1,4-dione
-
non-competitive inhibition towards shikimate and competitive inhibition towards ATP
2-[(4-chlorophenyl)amino]-N-(5-oxo-4,5-dihydro-1H-pyrazol-3-yl)acetamide
-
-
2-[(6-methyl-4-oxo-3-phenyl-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-2-yl)sulfanyl]acetamide
inhibitor identified by structure-based virtual screening, docking simulations
3,5-dichloro-N-[6-(5-hydroxy-3-methyl-1H-pyrazol-1-yl)pyridin-3-yl]benzenesulfonamide
-
-
3-methoxy-4-[2-[2-([2-methoxy-4-[(E)-(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]phenoxy]methyl)phenyl]ethyl]benzaldehyde
-
-
3-methoxy-4-[[2-([2-methoxy-4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]methyl)benzyl]oxy]benzaldehyde
-
noncompetitive inhibitor with respect to both shikimate and MgATP
3-phenyl-4-(5-sulfanyl-1H-tetrazol-1-yl)butanoic acid
inhibitor identified by structure-based virtual screening, docking simulations
3-[(5Z)-5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-N-(2-hydroxy-4-nitrophenyl)propanamide
-
-
3-[(8-methoxy-2-methyl-3-propylquinolin-4-yl)sulfanyl]propanoic acid
inhibitor identified by structure-based virtual screening, docking simulations
3-[[difluoro(4-methylphenyl)acetyl]amino]-N,1-dimethyl-1H-pyrazole-5-carboxamide
-
-
4-(5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-N-[4-(trifluoromethyl)phenyl]benzene-1-sulfonamide
-
-
4-[(Z)-[1-[2-(1,3-benzothiazol-2-yl)-3-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-pyrazol-4-yl]ethylidene]amino]-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
-
-
4-[(Z)-[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl]-2-ethoxyphenyl 3-nitrobenzoate
-
-
5-bromo-2-(5-[(E)-[1-(3,4-dichlorophenyl)-3,5-dioxopyrazolidin-4-ylidene]methyl]furan-2-yl)benzoic acid
-
-
5-bromo-2-(5-[[1-(3,4-dichlorophenyl)-3,5-dioxo-4-pyrazolidinylidene]methyl]-2-furyl)benzoic acid
-
competitive inhibitor toward shikimate and noncompetitive inhibitor with respect to MgATP
5-hydroxy-N-[[(2-oxo-4-phenyl-2H-1-benzopyran-7-yl)oxy]acetyl]-L-tryptophan
-
-
5-[(6S)-5-[[5-(hydroxymethyl)furan-2-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-6-yl]-3-[4-(trifluoromethoxy)phenyl]-2H-1,2,4-oxadiazol-1-ium
-
-
5-[[(2-bromo-6-chlorophenyl)acetyl]amino]-N,3-dimethyl-1H-pyrazole-4-carboxamide
-
-
5-[[(4-fluorobenzyl)sulfanyl]methyl]-4-methyl-4H-1,2,4-triazole-3-thiol
inhibitor identified by structure-based virtual screening, docking simulations
5-[[(4-fluorophenyl)acetyl]amino]-N,1-dimethyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.025 mg/ml
5-[[(4-fluorophenyl)acetyl]amino]-N-methyl-1-phenyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
5-[[(4-fluorophenyl)acetyl]amino]-N-methyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
5-[[(5-chloro-2-hydroxyphenyl)amino]methylidene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
6-cyclohexamidomanzamine A
6-deoxymanzamine X
-
noncompetitive inhibition
6-[3-(1,3-benzodioxol-5-yl)-1,2,4-oxadiazol-5-yl]-5-(3-phenylpropyl)-3a,4,5,6,7,7a-hexahydro-1H-imidazo[4,5-c]pyridine
-
-
8-hydroxymanzamine A
-
noncompetitive inhibition
alpha-linolenic acid
-
-
AMP
-
4 mM, 27% inhibition
caffeic acid
-
1 mM, 44% inhibition
disodium 7-amino-3-[(E)-(5-hydroxy-7-sulfonatonaphthalen-2-yl)diazenyl]naphthalene-2-sulfonate
-
-
EDTA
-
-
ethyl 4-[([(6S)-6-[4-(propan-2-yl)furan-2-yl]-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridin-5-yl]carbonyl)amino]benzoate
-
-
manzamine A
manzamine E
-
noncompetitive inhibition
manzamine F
-
noncompetitive inhibition
methyl 4-([[4-methoxy-2-(trifluoromethyl)benzyl]carbamoyl]amino)-1-methyl-1H-pyrazole-5-carboxylate
-
-
methyl 5-([[(5-chloro-2-methoxyphenyl)amino]acetyl]amino)-4-methyl-1H-pyrazole-3-carboxylate
-
-
N,1-dimethyl-5-([[4-(trifluoromethyl)phenyl]acetyl]amino)-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
N,1-dimethyl-5-[[(4-methylphenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of 0.025 mg/ml
N,1-dimethyl-5-[[(4-nitrophenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
N-(1,3-benzothiazol-2-yl)-6-(methylsulfanyl)-1,3-benzothiazol-2-amine
-
-
N-(2-cyclopropylbenzyl)-1-(2-hydroxyethyl)-1H-pyrazole-4-carboxamide
-
-
N-(3,5-dichloro-4-[[(methylsulfonyl)methyl]amino]phenyl)-5-oxo-4,5-dihydro-1H-pyrazole-3-carboxamide
-
IC50 of 0.025 mg/ml
N-(3-chloro-4-methylphenyl)-2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetamide
inhibitor identified by structure-based virtual screening, docking simulations
N-(4-hydroxyphenyl)-4-[4-oxo-5-[(Z)-2-phenylethenyl]-2-thioxo-1,3-thiazolidin-3-yl]butanamide
-
-
N-(5,7-dimethyl-1,3-benzothiazol-2-yl)-2-methoxybenzamide
-
-
N-methyl-1-phenyl-5-([[4-(trifluoromethyl)phenyl]acetyl]amino)-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
N-methyl-5-([[4-(trifluoromethyl)phenyl]acetyl]amino)-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
N-methyl-5-[[(4-methylphenyl)acetyl]amino]-1-phenyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.025 mg/ml
N-methyl-5-[[(4-methylphenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of 0.025 mg/ml
N-methyl-5-[[(4-nitrophenyl)acetyl]amino]-1-phenyl-1H-pyrazole-3-carboxamide
-
IC50 of 0.05 mg/ml
N-methyl-5-[[(4-nitrophenyl)acetyl]amino]-1H-pyrazole-3-carboxamide
-
IC50 of 0.1 mg/ml
N-[(2S)-2-[(2-oxo-4-propyl-2H-1-benzopyran-7-yl)oxy]propanoyl]-L-tryptophan
-
-
N-[(2S)-2-[(4-ethyl-2-oxo-2H-1-benzopyran-7-yl)oxy]propanoyl]-5-hydroxy-L-tryptophan
-
-
N-[3,5-dichloro-4-[(methylsulfonyl)amino]phenyl]-5-oxo-4,5-dihydro-1H-pyrazole-3-carboxamide
-
-
N-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]-3-phenoxybenzamide
-
-
N-[[(6-chloro-2-oxo-4-propyl-2H-1-benzopyran-7-yl)oxy]acetyl]-5-hydroxy-L-tryptophan
-
-
Na2SO4
-
5 mM, 27% inhibition
NaCl
-
250 mM, 50% inhibition
NSC162535
selective inhibitor, identification and binding analysis with enzyme mutant E144A by virtual docking analysis, isothermal titration calorimetry, and crystals structure analysis revealing an induced-fit mechanism, inactivation mechanism, detailed overview. Binding kinetics of wild-type and mutant enzymes
p-coumaric acid
-
1 mM, 14% inhibition
shikimate
substrate inhibition
shikimate 3-phosphate
-
-
sodium (3R,4R,5R)-3,4-dihydroxy-5-((perfluorophenyl)methoxy)-cyclohex-1-ene-1-carboxylate
sodium (3R,4R,5R)-3,4-dihydroxy-5-(3-nitrobenzyloxy)cyclohex-1-ene-1-carboxylate
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(1H-indol-5-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
sodium (3R,4S,5R)-3,4-dihydroxy-5-[[(naphthalen-2-yl)methyl]amino]cyclohex-1-ene-1-carboxylate
sodium (3R,4S,5R)-5-di(naphth-2-yl)methylamino-3,4-dihydroxycyclohex-1-eno-1-carboxylate
sodium (3R,4S,5R)-5-[bis[(1-benzothiophen-5-yl)methyl]amino]-3,4-dihydroxycyclohex-1-ene-1-carboxylate
sodium (3S,4R,5R)-3-amino-5-(benzo[b]thiophen-5-yl)-methoxy-4-hydroxycyclohex-1-ene-carboxylate
sodium (3S,4S,5R)-3-amino-4-hydroxy-5-(naphth-2-yl)-metoxycyclohex-1-ene-carboxylate
[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]acetic acid
inhibitor identified by structure-based virtual screening, docking simulations
[[1,3-dimethyl-9-(2-methylprop-2-en-1-yl)-2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-8-yl]sulfanyl]acetic acid
inhibitor identified by structure-based virtual screening, docking simulations
[[3-(2-methylprop-2-en-1-yl)-4-oxo-3,4,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-2-yl]sulfanyl]acetic acid
-
-
additional information
-