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5.4.99.5: chorismate mutase

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

Word Map on EC 5.4.99.5

Reaction

chorismate
=
prephenate

Synonyms

105-MtCM, 90-MtCM, AmtCM1, AmtCM2, aro7, AroA, AroH, AroQ, AtCM1, AtCM2, AtCM3, Bacillus subtilis chorismate mutase, Bphy_7813, BsAroH, BsCM, BsCM_2, BTH_I1596, chorismate mutase, chorismate mutase 1, chorismate mutase-prephenate dehydrogenase, Chorismate mutase/prephenate dehydratase, CM, CM type 2, CM-1, CM-prephenate dehydratase, CM-TyrAp, CM/PDT, CM/PDT/PDHG, CM0819, CM1, CM2, EcCM, EcCM-R, MI-CM-1, MI-CM-2, MjCM, MTB chorismate mutase, MTB CM, MtbCM, MtCM, Mutase, chorismate, Mycobacterium tuberculosis chorismate mutase, Mycobacterium tuberculosis H37Rv chorismate mutase, NC30, P protein, P-protein, PheA, PpCM1, PpCM2, Rv0948c, Rv1885c, SmCM, Tparo7, TtCM, y2828, YCM

ECTree

     5 Isomerases
         5.4 Intramolecular transferases
             5.4.99 Transferring other groups
                5.4.99.5 chorismate mutase

Inhibitors

Inhibitors on EC 5.4.99.5 - chorismate mutase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,2S,3S,5S,7S)-10-hydroxy-3-oxo-2-oxa-5-azatricyclo[4.3.1.1(4,8)]undecane-8-carboxylate
-
does not display tighter binding to the enzyme than the native substrate chorismate or greater inhibitory action than the ether analogue
(1R,3R,5S)-3-carboxy-1-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-5-carboxylate
(1R,3R,5S,8R)-2-azatricyclo[3.3.1.0(1,8)]-non-6-ene-3,5-dicarboxylate
-
exo arizidine analogue, no time-dependent loss of activity is observed in the presence of this potentially reactive aza inhibitor
(1R,3R,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
-
(1R,3R,5S,8R)-8-hydroxy-5-nitro-2-azabicyclo[3.3.1]non-6-ene-3-carboxylic acid
-
(1R,3R,5S,8R)-8-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid
-
(1R,3R,5S,8S)-8-hydroxy-2-azabicyclo[3.3.1]non-6-ene-3,5-dicarboxylate
-
does not display tighter binding to the enzyme than the native substrate chorismate or greater inhibitory action than the ether analogue
(1R,3S,5S,8R)-8-hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
-
(1R,3S,5S,8R)-8-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid
-
(1R,3S,5S,8S)-8-hydroxy-2-azabicyclo[3.3.1]non-6-ene-3,5-dicarboxylate
-
does not display tighter binding to the enzyme than the native substrate chorismate or greater inhibitory action than the ether analogue
(1R,3S,6S,8S,10S)-10-hydroxy-4-oxo-5-oxa-2-azatricyclo[4.3.1.13,8]undecane-8-carboxylic acid
-
(1R,5R,8R)-8-hydroxy-2-oxabicyclo[3.3.1]nona-3,6-diene-3,5-dicarboxylic acid
-
(1R,5S,8R)-8-hydroxy-2-azabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
-
(1S,2aR,2bR,3S)-4-oxohexahydro-1H-5-oxa-2b-aza-1,3-methanocyclopropa[cd]indene-1-carboxylic acid
-
(1S,3R,5R)-1-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid
(1S,3S,5R)-1-hydroxy-5-nitro-2-oxabicyclo[3.3.1]non-6-ene-3-carboxylic acid
(1S,3S,5R,6R)-6-hydroxy-4-oxabicyclo[3.3.1]non-7-ene-1,3-dicarboxylate
endo-oxabicyclic dicarboxylic acid is a good geometric mimic of transition state
(1S,4S,6R,8S,10S)-3-oxo-5-aza-2-oxa-tetracyclo[4.3.1.(4,8).0(6,10)]undecane-8-carboxylate
-
tetracyclic lactone, no time-dependent loss of activity is observed in the presence of this potentially reactive aza inhibitor
(2E)-8-exo-3-Hydroximino-8-hydroxy-2-oxabicyclo-[3.3.1]non-6-ene-5-carboxylic acid
-
poor
(2Z)-2-(4-chlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-enoic acid
-
(2Z)-2-(4-chlorophenyl)-3-[4-(dimethoxymethyl)-2-nitrophenyl]prop-2-enoic acid
competitive
(3R,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
(3S,6Z)-8-hydroxy-2-azabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
(3S,6Z)-8-hydroxy-2-oxabicyclo[3.3.3]undec-6-ene-3,5-dicarboxylic acid
-
(Z)-3-((5-nitrothiazol-2-yl)imino)indolin-2-one
-
-
(Z)-3-((6-nitrobenzo[d]thiazol-2-yl)imino)indolin-2-one
-
-
(Z)-3-(4-nitrobenzylidene)indolin-2-one
MIC is 0.0235 mM
(Z)-3-(hydroxyimino)indolin-2-one
-
-
(Z)-N-(1-acetyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
-
-
(Z)-N-(1-acetyl-2-oxoindolin-3-ylidene)hydrazinecarboxamide
-
-
(Z)-N-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide
-
-
(Z)-N-(2-oxoindolin-3-ylidene)hydrazinecarboxamide
-
-
1-(2-(tert-butyl)-5-chloro-7-(methylsulfonyl)-1H-indol-3-yl)ethan-1-one
45% inhibition at 0.03 mM
1-(prop-1-en-2-yl)indoline-2,3-dione
-
-
1-acetylindoline-2,3-dione
-
-
1-ethylindoline-2,3-dione
-
-
1-hydroxyadamantane
-
1-isopropyl-2-methoxy-4-methylbenzene
-
1-isopropylindoline-2,3-dione
-
-
1-methylindoline-2,3-dione
-
-
1-phenylindoline-2,3-dione
-
-
1-pivaloylindoline-2,3-dione
-
-
1-Substituted adamantane derivatives
-
order of decreasing inhibitory activity with the various substituents: -PO32-, -P(OCH3)O2, CO2-, -CH2CO2-, -SO2-,Y -SO3-
2-(1-Carboxy-1,4-dihydrobenzyl)acrylic acid
-
-
2-chloro-3-(5,6-difluoro-1H-indol-3-yl)quinoxaline
2-chloro-4-(ethoxycarbonyl)-1-hydroxy-6-methylquinolin-1-ium
-
2-isopropyl-5-methylphenyl acetate
-
2-methyl-5-(prop-1-en-2-yl)cyclohexanol
-
2-[2-[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]ethyl]-4-methylpentanoic acid
competitive
3-((5-nitrothiophen-2-yl)methylene)indolin-2-one
-
-
3-((dihydroxyamino)thio)-4-((3,5-dimethoxyphenethyl)amino)-5-nitrobenzoic acid
competitive
3-(3-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3d]pyrimidin-4[3H]-one
3-(4-nitrobenzylidene)indolin-2-one
-
-
3-amino-1-(3-(4-hydroxybut-1-yn-1-yl)phenyl)-1H-benzol[f]chromene-2-carbonitril
3-Chloroadamantane-1-acetic acid
-
-
3-chloroquinoxaline
-
3-endo,6-exo-6-Hydroxy-7-bicyclo[3.3.1]-nonene-1,3-dicarboxylic acid
-
poor
3-endo,8-exo-8-Hydroxy-2-oxabicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
-
potent
3-methyl-5-(propan-2-yl)phenol
-
4-(3,4-dimethoxyphenethylamino)-3-nitro-5-sulfamoylbenzoic acid
4-Methyl-DL-Trp
-
enzyme form CM1 is inhibited, enzyme form CM2 not
4-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-nitro-5-sulfamoylbenzoic acid
-
5,5'-dithiobis(2-nitrobenzoate)
-
-
5-(2,3-dichlorophenyl)indoline-2,3-dione
-
-
5-(2,5-dimethylphenyl)indoline-2,3-dione
-
-
5-(4-(3-(tert-butyl)phenyl)piperazin-1-yl)indoline-2,3-dione
-
-
5-(4-(furan-2-carbonyl)piperazin-1-yl)indoline-2,3-dione
-
-
5-(4-methylpiperazin-1-yl)indoline-2,3-dione
-
-
5-(piperazin-1-yl)indoline-2,3-dione
-
-
5-(piperidin-1-yl)indoline-2,3-dione
-
-
5-isopropyl-2-methylaniline
-
5-naphthyl-7-propyl-3H-pyrazolo-[4,3-d][1,2,3]triazin-4[5h]-one
5-naphthyl-7-propyl-3H-pyrazolo[4,3-d][1,2,3]triazin-4(5H)-one
-
5-phenylindoline-2,3-dione
-
-
6'-iodo-1,3-dihydro-1'H-spiro[indene-2,2'-quinazolin]-4'(3'H)-one
a spiro 2,3-dihydroquinazolin-4(1H)-one
6,6'-dinitro-[1,1'-biphenyl]-2,2'-dicarboxylic acid
-
6-hydroxyadamantane
-
6-hydroxybicyclo[3.3.1]nonane-1,3-dicarboxylic acid
-
6-Methyl-DL-Trp
-
enzyme form CM1 is inhibited, enzyme form CM2 not
8-exo-8-Hydroxy-2-oxabicyclo[3.3.1]nona-3,6-diene-3,5-dicarboxylic acid
-
slight
8-hydroxy-2-oxa-bicyclo[3.3.1]non-6-ene-3,5-dicarboxylic acid
-
competitive inhibition
adamantan phosphonic acid
-
Adamantane-1-acetic acid
adamantane-1-carboxylic acid
-
adamantane-1-phosphonate
-
no inhibitory effect up to concentrations of 0.1 and 1 mM
caffeic acid
carvacrol
chlorogenic acid
chorismate
DL-3-fluoro-Phe
-
enzyme form CM1 is inhibited, enzyme form CM2 not
DL-5-Fluoro-Trp
-
enzyme form CM1 is inhibited, enzyme form CM2 not
DL-5-hydroxy-Trp
-
enzyme form CM1 is inhibited, enzyme form CM2 not
endo-Oxabicylic transition state analogue inhibitor
-
-
-
ethyl 4-(2-(4-hydroxybut-1-yn-1-yl)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
-
ferulic acid
-
inhibits enzyme form CM3
iodoacetamide
-
-
L-Trp
96% residual activity at 0.2 mM
L-tryptophan
methyl 4-(methylamino)-3-nitrobenzoate
N-(4-fluoro-2-(5-fluoro-1-(methylsulfonyl)-1H-inden-2-yl)phenyl)methanesulfonamide
-
N-[(3-(2-amino-3-cyano-2H-benzo[h]chromen-4-y))phenyl]methylidyne]-2-hydroxyethanaminium
-
N-[[3-(tert-butoxycarbonyl)-2-phenyl-1,3-thiazolidin-4-yl]carbonyl]leucine
-
NaCl
-
inhibition is cooperative, NaCl also increases the sensitivity of the enzyme to inhibition by Phe
oxabicyclic dicarboxylic acid
transition state analogon, competitive inhibition
p-coumaric acid
-
inhibits enzyme form CM1, CM2 and CM3
phenylalanine
model of the AtCM1x02phenylalanine complex including residues Arg79-Val290 and Val307-Asp340, the phenylalanine ligand, and 83 waters, inhibits about 20fold
prephenate
Transition state analogue inhibitor
-
-
-
tyrosine
Zn2+
-
strong
additional information
-