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(1R,2R,6E)-8-(2,5-dihydroxyphenyl)-2-hydroxy-6-methyl-1-[[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl]oct-6-en-1-yl hydrogen sulfate
-
-
(1S,4bS,10aR,12aS)-10a-[(acetyloxy)methyl]-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-2-carboxylic acid
-
scarlarane sesterterpene, isolated from Smenospongia sp.
(2-bromo-4,5-dihydroxybenzyl)(2,3-dibromo-4,5-dihydroxybenzyl) ether
-
-
(2-bromo-4,5-dihydroxyphenyl)(3,4-dihydroxyphenyl) ether
-
-
(2E,6E)-9-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-2,6-dimethylnona-2,6-dienal
-
-
(2E,7E)-10-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-3,7-dimethyl-2-(2-methylprop-1-en-1-yl)deca-2,7-dienal
-
-
(2R)-2-[(3E,7E)-9-(hydroxymethyl)-4,8,11-trimethyldodeca-3,7,10-trien-1-yl]-2,8-dimethyl-3,4-dihydro-2H-chromen-6-ol
-
-
(2R,3R,4S,6E)-2-amino-1,3-dihydroxy-16-methylheptadec-6-en-4-yl hydrogen sulfate
-
(2S,7E)-9-(2,5-dihydroxyphenyl)-7-methyl-1-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]non-7-en-2-yl sulfate
-
-
(3-bromo-4,5-dihydroxyphenyl)(2,3-dibromo-4,5-dihydroxyphenyl)methanone
-
-
(4R,5R)-4-[(2E)-5-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-2-methylpent-2-en-1-yl]-2-methyl-5-(2-methylprop-1-en-1-yl)cyclopent-2-en-1-one
-
-
(4S,5bR,11aS,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
(4S,5bS,11aR,13aS,13bR)-11a-formyl-4-hydroxy-5b,8,8,13a-tetramethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
(4S,5bS,11aR,13aS,13bR)-11a-[(acetyloxy)methyl]-5b,8,8,13a-tetramethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1,4-diyl diacetate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
(5bR,7aS,11aR,11bS,13R,13aS,13bS)-1-hydroxy-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-13-yl acetate
-
(5bR,7aS,11aS,11bR,13R,13aS,13bR)-1-methoxy-5b,8,8,11a,13a-pentamethyl-3-oxo-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-13-yl acetate
-
(5bS,11aR,13aS,13bR)-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-3-oxo-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
(5E)-5-[(2R,6E,10E)-13-furan-3-yl-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methylfuran-2(5H)-one
-
linear furanosesterterpene, isolated from Smenospongia sp.
(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]-5-(3-methoxybenzylidene)furan-2(5H)-one
-
(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]-5-(4-methoxybenzylidene)furan-2(5H)-one
i.e. cadiolide H, purified from the ascidian Synoicum sp.
(5Z)-4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-(3,5-dibromo-4-hydroxybenzylidene)furan-2(5H)-one
i.e. cadiolide E, purified from the ascidian Synoicum sp.
(5Z)-4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-[(2,4-dibromo-3-hydroxyphenyl)methylidene]furan-2(5H)-one
-
(5Z)-5-(3-bromo-4-hydroxybenzylidene)-4-(3-bromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]furan-2(5H)-one
i.e. cadiolide G, purified from the ascidian Synoicum sp.
(5Z)-5-[(2R,5Z,9Z)-13-furan-3-yl-2,6,10-trimethyltrideca-5,9-dien-1-ylidene]-4-hydroxy-3-methylfuran-2(5H)-one
-
linear furanosesterterpene, isolated from Smenospongia sp.
(E)-2-(3-methylnon-2-enyl)benzene-1,4-diol
-
-
(E)-2-(4-hydroxy-3-methylbut-2-enyl)benzene-1,4-diol
-
-
(E)-2-(9-hydroxy-3-methylnon-2-enyl)benzene-1,4-diol
-
-
1,2-bis(5-hydroxy-1H-indol-3-yl)ethane-1,2-dione
-
-
1-(2-aminoethyl)-1H-indol-6-ol
-
-
1-(3-methoxyphenyl)-2,3,4,4a,9,9a-hexahydro-1H-b-carboline
-
1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-b-carboline
-
-
1-(4-ethylpiperazin-1-yl)-3-nitropropan-1-one
-
-
1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-b-carboline
-
-
1-(5-hydroxy-1H-indol-3-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione
i.e. hyrtiosin B
1-(naphthalen-2-yl)-2,3,4,9-tetrahydro-1H-b-carboline
-
-
1-carboxy-6-hydroxy-3,4-dihydro-beta-carboline
-
weak inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
1-cyclopropyl-6-fluoro-7-[4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
1-cyclopropyl-6-fluoro-7-[4-([(3Z)-3-[2-(methoxycarbamothioyl)hydrazinylidene]-5-methyl-2-oxo-2,3-dihydro-1H-indol-1-yl]methyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
1-cyclopropyl-7-(3,5-dimethyl-4-(3-nitropropanoyl)piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
1-cyclopropyl-7-[3,5-dimethyl-4-(3-nitropropanoyl)piperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
a fluoroquinolone derivative and structural analogue of succinate
1-ethyl-4-hydroxy-2-oxo-N'-tridecanoyl-1,2,3,4-tetrahydroquinoline-3-carbohydrazide
-
-
1-ethyl-6,8-difluoro-7-[3-methyl-4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
1-ethyl-6-fluoro-7-[4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
12-deacetoxy-23-acetoxy-19-O-acetylscalarin
-
cytotoxic, isolated from Smenospongia sp.
12-deacetoxy-23-acetoxyscalarin
-
cytotoxic, isolated from Smenospongia sp.
12-deacetoxy-23-hydroxyheteronemin
-
cytotoxic, isolated from Smenospongia sp.
2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane
-
-
2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenylmethane
-
-
2,2',3-tribromo-4,4',5,5'-tetrahydroxybibenzyl
-
-
2,2'-dibromo-4,4',5,5'-tetrahydroxybibenzyl
-
-
2,3-dibromo-4,5-dihydroxybenzyl alcohol
-
-
2,3-dibromo-4,5-dihydroxybenzyl methyl ether
-
-
2,5-dichloro-3-[(3E)-4-chloro-3-methylbut-3-en-1-yn-1-yl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
2-(3-methylbut-2-enyl)benzene-1,4-diol
-
-
2-(4-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 4-chloro-2-methoxybenzoate
2-(4-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
2-(4-hydroxyphenyl)-1-(5H-pyrido[4,3-b]indol-3-yl)ethan-1-one
-
2-(5-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 5-chloro-2-methoxybenzoate
2-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
2-allylbenzene-1,4-diol
-
-
2-hydroxy-1-(5-hydroxy-1H-indol-3-yl)ethanone
-
-
2-methylidenebutanedioic acid
-
i.e. itaconate
2-[(2E,7R,8R)-7,8-dihydroxy-3-methyl-9-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]non-2-en-1-yl]benzene-1,4-diol
-
-
3,4-dihydrohyrtiosulawesine
-
-
3,5-dibromo-4-hydroxyphenylethylamine
-
-
3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol
-
-
3-nitro-1-(4-phenylpiperazin-1-yl)propan-1-one
-
-
3-nitro-1-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-one
-
-
4,4'-(hexane-1,1-diyl)bis(6-bromobenzene-1,3-diol)
-
4,4'-(oxydimethanediyl)bis(5,6-dibromobenzene-1,2-diol)
-
-
4,4'-ethane-1,2-diyldibenzene-1,2-diol
-
-
4,4'-methanediylbis(5,6-dibromobenzene-1,2-diol)
-
-
4,4'-methanediylbis(5-bromobenzene-1,2-diol)
-
-
4,4'-methylenebis(5,6-dibromobenzene-1,2-diol)
-
-
4,5-dichloro-2-(5-chloro-2-methoxybenzamido)phenyl 5-chloro-2-methoxybenzoate
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
4-chloromercuribenzoate
-
complete inactivation at 0.001 mM
4-cyclopropyl-6-[3,5-dimethyl-4-(4-nitro-2-oxobutyl)piperazin-1-yl]-7-fluoro-5-methoxy-1-oxo-1,4,7,8-tetrahydronaphthalene-2-carboxylic acid
-
-
4-hydroxy-9-deoxoidiadione
-
cytotoxic, linear furanosesterterpene, isolated from Smenospongia sp.
4-[2-hydroxy-2-(5H-pyrido[4,3-b]indol-3-yl)ethyl]phenol
-
4-[[1-(4-chlorophenyl)-5-(6-methoxynaphthalen-2-yl)-3-oxopentyl]amino]benzoic acid
-
-
5,6-dichloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
5,6-dichloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
5-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
5-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
5-bromo-2-[[4-(trifluoromethyl)phenyl]carbamoyl]phenyl N-prop-1-en-2-yl-L-phenylalaninate
-
-
5-chloro-2-(4-chloro-2-methoxybenzamido)phenyl 4-chloro-2-methoxybenzoate
5-chloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
5-chloro-2-[[4-(trifluoromethyl)phenyl]carbamoyl]phenyl pyrazine-2-carboxylate
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
5-hydroxy-1H-indole-3-carbaldehyde
-
-
5-hydroxy-1H-indole-3-carboxylic acid methyl ester
-
weak inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
5-hydroxyindole-3-carbaldehyde
-
moderate inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
5-nitro-N'-[(E)-(5-nitrofuran-2-yl)methylidene]furan-2-carbohydrazide
-
-
6-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
6-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
6-chloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
6-hydroxy-4,9-dihydro-3H-beta-carboline-1-carboxylic acid
-
-
7-[3,5-dimethyl-4-[(5-nitro-2,6-dioxohexahydropyrimidin-4-yl)carbonyl]piperazin-1-yl]-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
-
-
ascorbate
-
enzyme is inhibited by an ascorbate plus Fe2+ system under aerobic conditions,16% residual activity at 2 mM ascorbate/0.02 mM Fe2+. Inactivation requires hydrogen peroxide, and can be prevented by catalase, EDTA, Mg2+, isocitrate, 20 mM glutathione, 20 mM dithiothreitol or 40 mM L-cysteine
ATP
-
35% inhibition at 2 mM
bis(2,3-dibromo-4,5-dihydroxyphenyl) ether
-
-
bis(2,3-dibromo-4,5-dihydroxyphenyl)methanone
-
bis(2-bromo-4,5-dihydroxyphenyl) ether
-
-
bis(3,4-dihydroxyphenyl)methanone
-
-
bis(3-bromo-4,5-dihydroxyphenyl)methanone
-
-
Cu2+
-
isoforms ICL1 and ICL2 are 60-80% inhibited by 5 mM Cu2+
D-fructose-6-phosphate
-
-
D-Glucose-6-phosphate
-
-
dimethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzoyl)-3-(3,5-dibromo-4-hydroxyphenyl)but-2-enedioate
i.e. synoilide A, purified from the ascidian Synoicum sp.
dimethyl (2Z)-2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate
i.e. synoilide B, purified from the ascidian Synoicum sp.
fructose-1,6-bisphosphate
GSSG
-
ICL can be inactivated by glutathionylation and reactivated by glutaredoxin after reduced dithiothreitol treatment, whereas thioredoxin does not appear to regulate ICL activity
hyrtiosin A
-
moderate inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
hyrtiosin B
-
strong inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
methyl (1R,4bS,10aR,12aS)-10a-[(acetyloxy)methyl]-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-2-carboxylate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
methyl (1S,4bS,10aR,12aS)-10a-[(acetyloxy)methyl]-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-2-carboxylate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate
methylmalonate
-
50% inhibition at 15 mM
Mg2+
-
isoform ICL2 is 20% inhibited by 5 mM Mg2+
N'1-[(4-nitrophenyl)methylene]-2-[3-(4-bromo-2-fluorobenzyl)-4-oxo-1,2,3,4-tetrahydro-1-phthalazinyl]ethanohydrazide
-
is the most active compound
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
N-(4-bromo-3-methylphenyl)-3-nitropropanamide
-
-
N-(4-bromophenyl)-3-nitropropanamide
-
-
N-(4-chlorophenyl)-3-nitropropanamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
oxaloacetate
-
89% inhibition at 10 mM
p-hydroxymercuribenzoate
-
complete inhibition at 0.016 mM
serotonin
-
moderate inhibition, isolated from marine sponge Hyrtios sp. (Thorectidae family)
sodium (2S)-5-furan-3-yl-2-[(1R)-1-hydroxy-2-[(1S,2R,4aR,8aR)-2-methyl-5-methylidenedecahydronaphthalen-1-yl]ethyl]pentyl sulfate
-
-
sodium 2,3-dihydroxypropyl (2R)-3-[[10-(2-hexylcyclopropyl)decanoyl]oxy]-2-hydroxypropyl phosphate
-
threo-DL-homoisocitrate
-
-
Urea
-
partial inactivation
XHD-1
-
extract of Illicium verum
-
XHD-2
-
extract of Zingiber officinale
-
[(5bS,11aR,13aS)-5b,8,8,13a-tetramethyl-5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a-tetradecahydrochryseno[1,2-c]furan-11a(4H)-yl]methanol
-
scarlarane sesterterpene, isolated from Smenospongia sp.
[(5bS,11aR,13aS)-5b,8,8,13a-tetramethyl-5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a-tetradecahydrochryseno[1,2-c]furan-11a(4H)-yl]methyl acetate
-
scarlarane sesterterpene, isolated from Smenospongia sp.
[(5bS,11aR,13aS,13bR)-1-methoxy-5b,8,8,13a-tetramethyl-1,5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a,13b-hexadecahydrochryseno[1,2-c]furan-11a(3H)-yl]methanol
-
scarlarane sesterterpene, isolated from Smenospongia sp.
2,5-dichloro-3-[(3E)-4-chloro-3-methylbut-3-en-1-yn-1-yl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2,5-dichloro-3-[(3E)-4-chloro-3-methylbut-3-en-1-yn-1-yl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2,5-dichloro-3-[(3E)-4-chloro-3-methylbut-3-en-1-yn-1-yl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
-
-
2-(4-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 4-chloro-2-methoxybenzoate
-
-
2-(4-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 4-chloro-2-methoxybenzoate
-
-
2-(4-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 4-chloro-2-methoxybenzoate
-
-
2-(4-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-(4-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-(4-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-(5-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 5-chloro-2-methoxybenzoate
-
-
2-(5-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 5-chloro-2-methoxybenzoate
-
-
2-(5-chloro-2-methoxybenzamido)-5-(trifluoromethyl)phenyl 5-chloro-2-methoxybenzoate
-
-
2-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)benzo[d]oxazole
-
-
2-mercaptoethanol
Candida brassicae
-
increase of activity
2-mercaptoethanol
-
increase of activity
2-oxoglutarate
-
19% inhibition at 5 mM
3-nitropropionate
-
0.133 mM, complete inhibition
3-nitropropionate
-
50% inhibition at 0.04 mM
3-nitropropionate
-
no growth of Mycobacterium tuberculosis on fatty acids after addition of 3-nitropropionate
3-nitropropionate
-
0.1 mM, inhibition of bacterial growth on and metabolisation of proprionate as sole carbon in absence of Vitamin B12
3-nitropropionate
-
a succinate analogue. Inhibition by 3-nitropropionate proceeds through an unusual double slow-onset process featuring formation of a complex with a Ki of 0.0033 mM during the first minute, followed by formation of a final complex with a Ki* of 44 nM over the course of several min to hours
3-nitropropionate
-
nearly complete inhibition at 6 mM
3-nitropropionate
-
irreversible inactivation
3-nitropropionic acid
-
-
3-nitropropionic acid
-
-
3-phosphoglycerate
-
-
3-phosphoglycerate
-
29% inhibition at 1 mM
4,5-dichloro-2-(5-chloro-2-methoxybenzamido)phenyl 5-chloro-2-methoxybenzoate
-
-
4,5-dichloro-2-(5-chloro-2-methoxybenzamido)phenyl 5-chloro-2-methoxybenzoate
-
-
4,5-dichloro-2-(5-chloro-2-methoxybenzamido)phenyl 5-chloro-2-methoxybenzoate
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5,6-dichloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5,6-dichloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5,6-dichloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5,6-dichloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5,6-dichloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5,6-dichloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-chloro-2-(4-chloro-2-methoxybenzamido)phenyl 4-chloro-2-methoxybenzoate
-
-
5-chloro-2-(4-chloro-2-methoxybenzamido)phenyl 4-chloro-2-methoxybenzoate
-
-
5-chloro-2-(4-chloro-2-methoxybenzamido)phenyl 4-chloro-2-methoxybenzoate
-
-
5-chloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-chloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-chloro-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
-
-
6-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-bromo-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-bromo-2-(5-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-chloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-chloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
6-chloro-2-(4-chloro-2-methoxyphenyl)benzo[d]oxazole
-
-
ADP
-
20% inhibition at 2 mM
Ba2+
-
-
Ca2+
-
-
citrate
-
22% inhibition at 5 mM
citrate
-
no inhibition at 0.1 mM
Cl-
-
-
Fe2+
-
isoforms ICL1 and ICL2 are 30% inhibited by 5 mM Fe2+
Fe2+
-
enzyme is inhibited by an ascorbate plus Fe2+ system under aerobic conditions,16% residual activity at 2 mM ascorbate/0.02 mM Fe2+. Inactivation requires hydrogen peroxide, and can be prevented by catalase, EDTA, Mg2+, isocitrate, 20 mM glutathione, 20 mM dithiothreitol or 40 mM L-cysteine
fructose-1,6-bisphosphate
-
-
fructose-1,6-bisphosphate
-
39% inhibition at 5 mM
fructose-1,6-bisphosphate
-
-
fumarate
-
-
fumarate
-
no inhibition at 0.1 mM
glucose-6-phosphate
-
44% inhibition at 5 mM
glutathione
Candida brassicae
-
increase of activity
glycolate
-
-
glycolate
Candida brassicae
-
-
glycolate
-
50% inhibition at 5 mM
glycolate
-
20% inhibition at 1 mM
glycolate
Lupinus sp.
-
-
glyoxylate
-
linear competitive inhibitor
glyoxylate
Lupinus sp.
-
-
H2O2
-
incubation with 0.1 mM H2O2 and 0.5mM GSH for 30 min results in a decrease of protein activity comparable with that obtained in the presence of GSSG. The addition of reduced dithiothreitol provides full reactivation of enzyme activity. Exposure to 1 mM H2O2 for 30 min results in an almost complete inactivation of the enzyme, whereas in the presence of a 10fold lower concentration of H2O2 (0.1 mM), ICL retains 20% of total activity after 30 min of incubation. GSH, reacting with sulfenic acid, can protect the protein from H2O2-mediated irreversible inactivation by glutathionylation
H2O2
-
inhibits enzyme activity with increased concentrations, no activity above 1.3 mM
HgCl2
-
100% inhibition at 0.01 mM
HgCl2
-
30% inhibition at 0.1 mM
HPO42-
-
-
Hydroxymalonate
-
-
Hydroxymalonate
-
50% inhibition at 0.5 mM
iodoacetate
-
isocitrate protects
iodoacetate
-
70% inhibition at 10 mM
Itaconate
-
-
Itaconate
-
89% inhibition at 1 mM
Itaconate
-
a succinate analogue lacking an acidic alpha-proton, the inhhibitor does not display slow-binding behavior
Itaconate
-
uncompetitive with respect to isocitrate
Itaconic acid
-
potent competitive inhibitor of ICL, 1 mg/ml reduces the activity to 42% of the uninhibited control. Inhibition of ICL enzymatic activity during chronic infection of rats forces the infection into an acute phase
Itaconic acid
-
itaconic acid specifically inhibits growth of wild-type cells on acetate and propionate, but not dextrose, in an ICL-dependent manner, and elicited metabolomic changes similar to those observed with ICL-deficient cells. Enzyme ICL inhibition by itaconic acid results in a specific decrease in intrabacterial pH from pH 7.3 to pH 6.4 in propionate-grown cells, not in acetate-grown cells
KCl
-
at pH-values above 8.6 inhibition, below pH 8.6 activation by KCl
KCl
-
strong activation by KCl
malate
Lupinus sp.
-
-
malate
-
Icl enzyme, 50% inhibition at 5 mM
malate
-
no inhibition at 0.1 mM
malate
-
competitive mode
Maleate
-
condensation reaction
Maleate
-
66% inhibition at 0.5 mM
malonate
-
-
malonate
-
condensation reaction
malonate
Candida brassicae
-
-
methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate
i.e. cadiolide I, purified from the ascidian Synoicum sp.
methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate
-
methylenesuccinate
-
-
methylenesuccinate
-
condensation reaction
methylenesuccinate
Lupinus sp.
-
-
methylenesuccinate
-
87% inhibition at 0.03 mM
Mn2+
-
isoform ICL1 is 40% inhibited by 5 mM Mn2+
Mn2+
Candida brassicae
-
inhibition in presence of Mg2+, activation in absence of Mg2+
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
-
-
N-ethylmaleimide
Lupinus sp.
-
-
N-ethylmaleimide
-
40% inhibition at 1 mM
NaCl
-
activation by NaCl
NO3-
-
-
oxalacetate
-
50% inhibition at 5 mM
oxalate
-
-
oxalate
-
86% inhibition at 10 mM
oxalate
-
77% inhibition at 1 mM
oxalate
-
Icl enzyme, 50% inhibition at 5 mM
oxalate
-
71% inhibition at 0.5 mM
p-chloromercuribenzoate
-
100% inhibition at 0.02 mM, reversible by 2-mercaptoethanol
p-chloromercuribenzoate
Lupinus sp.
-
-
p-chloromercuribenzoate
-
reversible by cysteine
p-chloromercuribenzoate
-
70% inhibition at 0.1 mM
phosphate
-
-
phosphate
-
nonlinear competitive inhibitor, inhibition model
phosphoenolpyruvate
-
-
phosphoenolpyruvate
-
uncompetitive inhibitor
phosphoenolpyruvate
-
90% inhibition at 2 mM
phosphoenolpyruvate
Lupinus sp.
-
-
phosphoenolpyruvate
-
53% inhibition at 1 mM
pyruvate
-
58% inhibition at 5 mM
pyruvate
-
87% inhibition at 10 mM
SO42-
-
-
Sr2+
-
-
succinate
-
33% inhibition at 10 mM
succinate
Candida brassicae
-
-
succinate
-
21% inhibition at 5 mM
succinate
-
90% inhibition at 5 mM
succinate
-
38% inhibition at 1 mM
succinate
Lupinus sp.
-
-
succinate
-
AceA enzyme, 50% inhibition at 5 mM
succinate
-
competitive mode
succinate
-
7% inhibition at 0.5 mM
sulfhydryl compounds
-
increase of activity
sulfhydryl compounds
-
increase of activity
Tartrate
-
-
Tartrate
-
33% inhibition at 0.5 mM
Zn2+
-
isoforms ICL1 and ICL2 are 60-80% inhibited by 5 mM Zn2+
Zn2+
Candida brassicae
-
-
additional information
-
6-hydroxy-3,4-dihydro-1-oxo-beta-carboline, isolated from marine sponge Hyrtios sp. (Thorectidae family), defined inactive as inhibitor since IC50 is higher than 0.989 mM at a concentration of 2 mg/ml
-
additional information
-
natural glyoxylate cycle inhibitors such 5-hydroxyindole-type alkaloids are potent inhibitors
-
additional information
cadiolide and synoilide ICL inhibitors (5Z)-4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-(3,5-dibromo-4-hydroxybenzylidene)furan-2(5H)-one, (5Z)-5-(3-bromo-4-hydroxybenzylidene)-4-(3-bromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]furan-2(5H)-one, (5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]-5-(4-methoxybenzylidene)furan-2(5H)-one, methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate, dimethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzoyl)-3-(3,5-dibromo-4-hydroxyphenyl)but-2-enedioate and dimethyl (2Z)-2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate have no inhibitory effects on Candida albicans strain SC5314 grown in glucose, but are inhibitory to strain SC5314 grown in acetate
-
additional information
-
cadiolide and synoilide ICL inhibitors (5Z)-4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-(3,5-dibromo-4-hydroxybenzylidene)furan-2(5H)-one, (5Z)-5-(3-bromo-4-hydroxybenzylidene)-4-(3-bromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]furan-2(5H)-one, (5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]-5-(4-methoxybenzylidene)furan-2(5H)-one, methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate, dimethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzoyl)-3-(3,5-dibromo-4-hydroxyphenyl)but-2-enedioate and dimethyl (2Z)-2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate have no inhibitory effects on Candida albicans strain SC5314 grown in glucose, but are inhibitory to strain SC5314 grown in acetate
-
additional information
-
degradation of the aceA mRNA, encoding the enzyme, by RNase E/G, that cleaves the aceA mRNA at a single-stranded AU-rich region in the 3' untranslated region. The level of aceA mRNA is approximately 3fold higher in the rneG knockout mutant strain compared to the wild-type strain
-
additional information
-
reversible loss of activity in isocitrate lyase from Haloferax volcanii when the enzyme is out of extract without a thiol, such as dithiothreitol
-
additional information
-
design, synthesis, and in vitro antimycobacterial activities against human hepatic cells of a series of 2-methoxy-2'-hydroxybenzanilide derivatives and their thioxo analogues, overview
-
additional information
-
design, synthesis, and in vitro antimycobacterial activities against human hepatic cells of a series of 2-methoxy-2'-hydroxybenzanilide derivatives and their thioxo analogues, overview
-
additional information
-
some 2-[3-(4-bromo-2-fluorobenzyl)-4-oxo-3,4-dihydro-1-phthalazinyl]acetic acid hydrazones show 45-61% inhibition at 10 mM
-
additional information
-
extracts of Illicium verum and Zingiber officinale inhibit ICL
-
additional information
-
design, synthesis, inhibitory potencies against the enzyme, and in vitro antimycobacterial activities against human hepatic cells of a series of 2-methoxy-2'-hydroxybenzanilide derivatives and their thioxo analogues, overview
-
additional information
-
not inhibited by bromopyruvate
-
additional information
-
halisulfates from the tropical sponge Hippospongia sp. are able to inhibit ICL activity, appressorium formation and C2 utilization
-
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0.0126
(1R,2R,6E)-8-(2,5-dihydroxyphenyl)-2-hydroxy-6-methyl-1-[[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl]oct-6-en-1-yl hydrogen sulfate
Pyricularia grisea
-
-
0.01561
(2-bromo-4,5-dihydroxybenzyl)(2,3-dibromo-4,5-dihydroxybenzyl) ether
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.06819
(2-bromo-4,5-dihydroxyphenyl)(3,4-dihydroxyphenyl) ether
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.185
(2E,6E)-9-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-2,6-dimethylnona-2,6-dienal
Candida albicans
-
pH 7.0, 37°C
0.1729
(2E,7E)-10-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-3,7-dimethyl-2-(2-methylprop-1-en-1-yl)deca-2,7-dienal
Candida albicans
-
pH 7.0, 37°C
0.1184
(2R)-2-[(3E,7E)-9-(hydroxymethyl)-4,8,11-trimethyldodeca-3,7,10-trien-1-yl]-2,8-dimethyl-3,4-dihydro-2H-chromen-6-ol
Candida albicans
-
pH 7.0, 37°C
0.00265
(3-bromo-4,5-dihydroxyphenyl)(2,3-dibromo-4,5-dihydroxyphenyl)methanone
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.141
(4R,5R)-4-[(2E)-5-[(2R)-6-hydroxy-2,8-dimethyl-3,4-dihydro-2H-chromen-2-yl]-2-methylpent-2-en-1-yl]-2-methyl-5-(2-methylprop-1-en-1-yl)cyclopent-2-en-1-one
Candida albicans
-
pH 7.0, 37°C
0.01716
(5Z)-4-(3,5-dibromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]-5-(4-methoxybenzylidene)furan-2(5H)-one
Candida albicans
pH and temperature not specified in the publication
0.00762
(5Z)-4-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)-5-(3,5-dibromo-4-hydroxybenzylidene)furan-2(5H)-one
Candida albicans
pH and temperature not specified in the publication
0.0488
(5Z)-5-(3-bromo-4-hydroxybenzylidene)-4-(3-bromo-4-hydroxyphenyl)-3-[(S)-(3,5-dibromo-4-methoxyphenyl)(hydroxy)methyl]furan-2(5H)-one
Candida albicans
pH and temperature not specified in the publication
0.4
(E)-2-(3-methylnon-2-enyl)benzene-1,4-diol
Candida albicans
-
-
0.29
(E)-2-(4-hydroxy-3-methylbut-2-enyl)benzene-1,4-diol
Candida albicans
-
-
0.28
(E)-2-(9-hydroxy-3-methylnon-2-enyl)benzene-1,4-diol
Candida albicans
-
-
0.089
1,2-bis(5-hydroxy-1H-indol-3-yl)ethane-1,2-dione
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.301
1-(2-aminoethyl)-1H-indol-6-ol
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.075
1-(3-methoxyphenyl)-2,3,4,9-tetrahydro-1H-b-carboline
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.0126
1-(4-ethylpiperazin-1-yl)-3-nitropropan-1-one
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.18
1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-b-carboline
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.137
1-(naphthalen-2-yl)-2,3,4,9-tetrahydro-1H-b-carboline
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.379
1-carboxy-6-hydroxy-3,4-dihydro-beta-carboline
Candida albicans
-
0.874 mg/ml
0.00012
1-cyclopropyl-6-fluoro-7-[4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0001
1-cyclopropyl-7-(3,5-dimethyl-4-(3-nitropropanoyl)piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0001
1-cyclopropyl-7-[3,5-dimethyl-4-(3-nitropropanoyl)piperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.00146
1-ethyl-6,8-difluoro-7-[3-methyl-4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.0002
1-ethyl-6-fluoro-7-[4-(3-nitropropanoyl)piperazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.002
2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.0028
2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenylmethane
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.01477
2,2',3-tribromo-4,4',5,5'-tetrahydroxybibenzyl
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.02121
2,2'-dibromo-4,4',5,5'-tetrahydroxybibenzyl
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.0926
2,3-dibromo-4,5-dihydroxybenzyl alcohol
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.1256
2,3-dibromo-4,5-dihydroxybenzyl methyl ether
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.61
2-(3-methylbut-2-enyl)benzene-1,4-diol
Candida albicans
-
-
1.02
2-allylbenzene-1,4-diol
Candida albicans
-
-
0.318
2-hydroxy-1-(5-hydroxy-1H-indol-3-yl)ethanone
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.015
2-[(2E,7R,8R)-7,8-dihydroxy-3-methyl-9-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]non-2-en-1-yl]benzene-1,4-diol
Pyricularia grisea
-
-
0.0929
3,4-dihydrohyrtiosulawesine
Candida albicans
-
pH and temperature not specified in the publication
0.116
3,5-dibromo-4-hydroxyphenylethylamine
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.0021
3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
0.04121
3-nitro-1-(4-phenylpiperazin-1-yl)propan-1-one
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.03018
3-nitro-1-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-one
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.00166 - 0.0924
3-nitropropionate
0.116
3-nitropropionic acid
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.02806
4,4'-(oxydimethanediyl)bis(5,6-dibromobenzene-1,2-diol)
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.05847
4,4'-ethane-1,2-diyldibenzene-1,2-diol
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.01844
4,4'-methanediylbis(5,6-dibromobenzene-1,2-diol)
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.04615
4,4'-methanediylbis(5-bromobenzene-1,2-diol)
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.0039
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00314
4-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.02537
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00574
4-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.01152
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00316
4-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00734
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00511
4-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.08702
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00849
4-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00491
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00369
5-chloro-N-(2-hydroxy-4-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.01543
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00586
5-chloro-N-(2-hydroxy-5-(trifluoromethyl)phenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00298
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00372
5-chloro-N-(4,5-dichloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.0513
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00445
5-chloro-N-(4-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.0086
5-chloro-N-(5-chloro-2-hydroxyphenyl)-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.247
5-hydroxy-1H-indole-3-carbaldehyde
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.799
5-hydroxy-1H-indole-3-carboxylic acid methyl ester
Candida albicans
-
0.153 mg/ml
0.247
5-hydroxyindole-3-carbaldehyde
Candida albicans
-
0.0398 mg/ml
0.38
6-hydroxy-4,9-dihydro-3H-beta-carboline-1-carboxylic acid
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.01163
bis(2,3-dibromo-4,5-dihydroxyphenyl) ether
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.03088
bis(2-bromo-4,5-dihydroxyphenyl) ether
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.02258
bis(3,4-dihydroxyphenyl)methanone
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.00889
bis(3-bromo-4,5-dihydroxyphenyl)methanone
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.6
CdCl2
Mycobacterium tuberculosis
-
-
0.07517
dimethyl (2Z)-2-(3,5-dibromo-4-hydroxybenzoyl)-3-(3,5-dibromo-4-hydroxyphenyl)but-2-enedioate
Candida albicans
pH and temperature not specified in the publication
0.1216
dimethyl (2Z)-2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate
Candida albicans
pH and temperature not specified in the publication
0.318
hyrtiosin A
Candida albicans
-
0.061 mg/ml
0.089
hyrtiosin B
Candida albicans
-
0.285 mg/ml
0.06
Itaconate
Candida albicans
-
-
0.0033
itaconic anhydride
Mycobacterium tuberculosis
-
in 50 mM potassium phosphate, 4 mM MgCl2, 4 mM phenylhydrazine, 12 mM cysteine, pH 7.0, at 37°C
0.01036
methyl 2-[bis(3,5-dibromo-4-hydroxyphenyl)methylidene]-4-(3,5-dibromo-4-hydroxyphenyl)-5-oxo-2,5-dihydrofuran-3-carboxylate
Candida albicans
pH and temperature not specified in the publication
0.04662
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00388
N-(4-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00798
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.0076
N-(4-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.0368
N-(4-bromo-3-methylphenyl)-3-nitropropanamide
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.03246
N-(4-bromophenyl)-3-nitropropanamide
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.02132
N-(4-chlorophenyl)-3-nitropropanamide
Mycobacterium tuberculosis
-
pH not specified in the publication, temperature not specified in the publication
0.00563
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00653
N-(5-bromo-2-hydroxyphenyl)-4-chloro-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00409
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.00874
N-(5-bromo-2-hydroxyphenyl)-5-chloro-2-methoxybenzothioamide
Mycobacterium tuberculosis
-
pH 7.0, 37°C
0.301
serotonin
Candida albicans
-
0.053 mg/ml
0.0674
sodium (2S)-5-furan-3-yl-2-[(1R)-1-hydroxy-2-[(1S,2R,4aR,8aR)-2-methyl-5-methylidenedecahydronaphthalen-1-yl]ethyl]pentyl sulfate
Pyricularia grisea
-
-
5
succinate
Aspergillus fumigatus
-
in 50 mM MOPS buffer, pH 7.5, with 1 mM MgCl2, 10 mM 2-mercaptoethanol, and 2.7 mM O-nitrophenyl-beta-D-galactopyranoside
0.0477
XHD-1
Mycobacterium tuberculosis
-
in 50 mM potassium phosphate, 4 mM MgCl2, 4 mM phenylhydrazine, 12 mM cysteine, pH 7.0, at 37°C
-
0.0182
XHD-2
Mycobacterium tuberculosis
-
in 50 mM potassium phosphate, 4 mM MgCl2, 4 mM phenylhydrazine, 12 mM cysteine, pH 7.0, at 37°C
-
0.8
ZnCl2
Mycobacterium tuberculosis
-
-
additional information
(4S,5bR,11aS,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
0.00166
3-nitropropionate
Candida albicans
pH and temperature not specified in the publication
0.0348
3-nitropropionate
Candida albicans
-
pH 7.0, 37°C
0.0507
3-nitropropionate
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.051
3-nitropropionate
Candida albicans
-
pH not specified in the publication, temperature not specified in the publication
0.0924
3-nitropropionate
Pyricularia grisea
-
-
0.0924
3-nitropropionate
Pyricularia grisea
-
in 20 mM sodium phosphate buffer (pH 7.0), with 3.75 mM MgCl2 and 4.1 mM phenylhydrazine, at 37°C
additional information
(4S,5bR,11aS,13aS,13bR)-4-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
Candida albicans
-
> 0.1 mg/ml
additional information
(4S,5bS,11aR,13aS,13bR)-11a-formyl-4-hydroxy-5b,8,8,13a-tetramethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
Candida albicans
-
> 0.1 mg/ml
additional information
(4S,5bS,11aR,13aS,13bR)-11a-[(acetyloxy)methyl]-5b,8,8,13a-tetramethyl-1,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1,4-diyl diacetate
Candida albicans
-
> 0.1 mg/ml
additional information
(5bS,11aR,13aS,13bR)-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-3-oxo-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[1,2-c]furan-1-yl acetate
Candida albicans
-
> 0.1 mg/ml
additional information
(5E)-5-[(2R,6E,10E)-13-furan-3-yl-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methylfuran-2(5H)-one
Candida albicans
-
0.027 mg/ml
additional information
(5Z)-5-[(2R,5Z,9Z)-13-furan-3-yl-2,6,10-trimethyltrideca-5,9-dien-1-ylidene]-4-hydroxy-3-methylfuran-2(5H)-one
Candida albicans
-
0.0312 mg/ml
additional information
12-deacetoxy-23-acetoxy-19-O-acetylscalarin
Candida albicans
-
> 0.1 mg/ml
additional information
12-deacetoxy-23-acetoxyscalarin
Candida albicans
-
0.0672 mg/ml
additional information
12-deacetoxy-23-hydroxyheteronemin
Candida albicans
-
> 0.1 mg/ml
additional information
3-nitropropionate
Candida albicans
-
0.006 mg/ml
additional information
4-hydroxy-9-deoxoidiadione
Candida albicans
-
> 0.1 mg/ml
additional information
methyl (1R,4bS,10aR,12aS)-10a-[(acetyloxy)methyl]-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-2-carboxylate
Candida albicans
-
0.055 mg/ml
additional information
methyl (1S,4bS,10aR,12aS)-10a-[(acetyloxy)methyl]-1-formyl-4b,7,7,12a-tetramethyl-1,4,4a,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-2-carboxylate
Candida albicans
-
> 0.1 mg/ml
additional information
[(5bS,11aR,13aS)-5b,8,8,13a-tetramethyl-5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a-tetradecahydrochryseno[1,2-c]furan-11a(4H)-yl]methanol
Candida albicans
-
0.0457 mg/ml
additional information
[(5bS,11aR,13aS)-5b,8,8,13a-tetramethyl-5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a-tetradecahydrochryseno[1,2-c]furan-11a(4H)-yl]methyl acetate
Candida albicans
-
> 0.1 mg/ml
additional information
[(5bS,11aR,13aS,13bR)-1-methoxy-5b,8,8,13a-tetramethyl-1,5,5a,5b,6,7,7a,8,9,10,11,11b,12,13,13a,13b-hexadecahydrochryseno[1,2-c]furan-11a(3H)-yl]methanol
Candida albicans
-
0.042 mg/ml
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evolution
the enzyme belongs to the isocitrate lyase ICL subfamily 3, one of two eubacterial groups, it has a substitution of M504I compared to the cold-adapted ICLs, rendering is less thermostable, phylogenetic analysis, overview
evolution
the ICL family includes five subfamilies, and the 2-methylisocitrate lyase (MICL) family. The ICL from Pseudomonas aeruginosa (ICL-Pa) is identified in a different ICL node (subfamily 3) than other Pseudomonas ICL enzymes, phylogenetic analysis
evolution
-
the enzyme belongs to the isocitrate lyase ICL subfamily 3, one of two eubacterial groups, it has a substitution of M504I compared to the cold-adapted ICLs, rendering is less thermostable, phylogenetic analysis, overview
-
malfunction
-
a mutant deleted of the ICL gene (acuD) is fully virulent in a murine model
malfunction
-
an ICL-deficient mutant is unable to utilize acetate, ethanol, citrate, glycerol, oleate, lactate, pyruvate, peptone, glutamate or alanine for growth, unlike the parental strain. ICL-deficient mutant is unable to utilize nonfermentable carbon sources and has reduced virulence in mice
malfunction
-
an ICL1 mutant shows the same number of subarachnoidal yeast cells as the wild-type after 10 days in immunosuppressed rabbits. In an inhalation model of murine cryptococcosis, no differences in survival between an ICL1 mutant and the wild-type
malfunction
-
deletion of the ICL1 gene causes a reduction in appressorium formation, conidiogenesis and cuticle penetration, and an overall decrease in damage to leaves of rice and barley
malfunction
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ICL (aceA) mutant displays reduced virulence on alfalfa seedlings and a reduction in histopathology in rat lungs
malfunction
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ICL1 mutant fails to grow on acetate or fatty acids, but is able to germinate and develop appressoria and is capable of degrading lipid bodies as well as the wild-type strain. Conidia from the ICL1-deficient mutant inoculated onto cucumber leaves and cotyledons form a reduced number of lesions on leaves, and especially on cotyledons, but nevertheless remain pathogenic. In invasive experiments such as the inoculation of conidia into wound sites, no defect is observed in the ICL1 mutant, while in penetration assays on cucumber cotyledons the mutant is unable to develop penetrating hyphae
malfunction
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inhibiting the activity of this enzyme during experimental chronic lung infection of rats forces the infection into an acute state, which can then be treated with antibiotics. If antibiotics are not provided in combination with isocitrate lyase inhibitors, the resulting infection overwhelms the host, resulting in death. ICL mutant is hypervirulent, it does not establish a chronic infection but establishes an acute infection. ICL mutants are significantly more cytotoxic than other strains. Complementation of the mutant strain restores the wild-type phenotype
malfunction
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mutations in the sole ICL gene (aceA) prevent growth on acetate but do not affect pathogenesis in a mouse model
malfunction
nutrient-starved bacilli lacking the glyoxylate shunt enzyme isocitrate lyase fail to reduce their intracellular ATP level and die, thus establishing a link between ATP control and intermediary metabolism. ICL loss-of-function mutant dies in the Loebel model. Viability is fully restored when the mutant strain is complemented with a wild-type copy of ICL
malfunction
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population of an ICL-deficient strain increases in macrophages after 12 h but then decline significantly
malfunction
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single ICL mutations have no dramatic effect on the growth. ICL mutant has a reduced ability to sustain the infection. An ICL/AceA double mutant is unable to grow on carbon source. The double mutant inoculated into mice is eliminated from lungs and spleen and is unable to induce splenomegaly or alterations in lungs
malfunction
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an aceA mutant displays enhanced biofilm formation during anaerobic growth. Expression of PcrV, of PopN (a regulator of the T3SS translocation process), ExoS (a T3 effector protein), and ExsD (a T3S regulator) is greatly reduced in the aceA mutant. Expression of aceA from a plasmid in trans can restore PcrV expression and ICL activity in the aceA mutant
malfunction
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enzyme-deficient cells undergo a progressive depletion of TCA cycle intermediates and accumulation of propionyl-CoA when metabolizing fatty acid substrates, phenotype, overview. Enzyme-deficient cells are unable to metabolize both even- and odd-chain fatty acids because of the dead-end depletion of TCA cycle intermediates by a constitutively active, but broken, methylcitrate cycle. Addition of cobalamin is sufficient to selectively protect ICL-deficient cells from the bactericidal effects of acetate and propionate, and this attenuation is accompanied by a dose-dependent restoration of TCA cycle activity and propionyl-CoA levels
malfunction
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enzyme-deficient Mycobacterium tuberculosis strains are significantly more susceptible than wild type to the antibiotics isoniazid, rifampicin, and streptomycin
malfunction
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enzyme-deficient Mycobacterium tuberculosis strains are significantly more susceptible than wild type to the antibiotics isoniazid, rifampicin, and streptomycin
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malfunction
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nutrient-starved bacilli lacking the glyoxylate shunt enzyme isocitrate lyase fail to reduce their intracellular ATP level and die, thus establishing a link between ATP control and intermediary metabolism. ICL loss-of-function mutant dies in the Loebel model. Viability is fully restored when the mutant strain is complemented with a wild-type copy of ICL
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metabolism
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ICL overexpression and malonate addition has a significant impact on metabolism and on organic acid production profiles. Increased ICL expression does not result in an increased glyoxylate bypass flux, there is a global response with respect to gene expression, leading to an increased flux through the oxidative part of the TCA cycle. Instead of an increased production of succinate and malate, a major increase in fumarate production is observed. In the strain with overexpression of ICL the organic acid production shifts from fumarate towards malate production when malonate is added to the cultivation medium
metabolism
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participation of isoforms in metabolic regulation of the glyoxylate cycle, organic acid metabolism during photorespiration in leaves and acidosis in corn seeds
metabolism
glyoxylate cycle key enzyme
metabolism
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high activity in isolates from cystic fibrosis patients
metabolism
-
first enzyme of the glyoxylate shunt, which allows for the anaplerosis of citric acid cycle intermediates under nutrient limiting conditions
metabolism
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isocitrate lyase is a key enzyme in the glyoxylate cycle
metabolism
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the enzyme is important in the glyoxylate shunt pathway, which is strongly induced in Pseudomonas aeruginosa during anaerobic growth and during growth on C2-sources, such as acetate or fatty acids, as the sole carbon source, overview
metabolism
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the enzyme is an essential component of the glyoxylate cycle
metabolism
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the enzyme is an essential component of the glyoxylate cycle
metabolism
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the enzyme is required for the utilization of poly-beta-hydroxybutyrate for energy deriving during carbon starvation
metabolism
-
the function of isoform ICL1 is related to the glyoxylate cycle while isoform ICL2 functions independently from the glyoxylate cycle and interconverts organic acids in the cytosol
metabolism
-
ICL overexpression and malonate addition has a significant impact on metabolism and on organic acid production profiles. Increased ICL expression does not result in an increased glyoxylate bypass flux, there is a global response with respect to gene expression, leading to an increased flux through the oxidative part of the TCA cycle. Instead of an increased production of succinate and malate, a major increase in fumarate production is observed. In the strain with overexpression of ICL the organic acid production shifts from fumarate towards malate production when malonate is added to the cultivation medium
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metabolism
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isocitrate lyase is a key enzyme in the glyoxylate cycle
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physiological function
ICL gene is required for non-growing survival in the Loebel model (nutrient deprivation in oxygen-rich medium)
physiological function
-
ICL is essential for full virulence in the organism
physiological function
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ICL is essential for long-term survival and proliferation in macrophages
physiological function
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ICL is required for persistence during chronic infection, but not for acute lethal infection in mice
physiological function
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ICL1 contributes to virulence but is not essential for systemic infection. Role for the beta-oxidation pathway in virulence
physiological function
-
important role for ICL in fungal virulence on plants. The ICL1 gene is expressed during its infection of Brassica napus cotyledons and inactivation of this locus causes low germination rates of pycnidiospores, reducing the pathogenicity of the fungus on cotyledons as well as limiting its hyphal growth on canola
physiological function
-
isocitrate lyase is a persistence factor. ICL is not required for survival within unactivated murine macrophage cells
physiological function
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lack of correlation between ICL gene expression and biological function
physiological function
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the glyoxylate cycle mediated by ICL is unnecessary for virulence
physiological function
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the organism constitutively produces ICL
physiological function
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two functional ICLs
physiological function
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two functional ICLs. ICL has a pivotal role in bacterial persistence in the host. ICL activity is essential for survival in the host. ICL and to a lesser extent AceA are required for the growth on propionate and on odd-chain fatty acids as a carbon source. The organism possesses dual ICL/MICL activity and can support growth on acetate and propionate
physiological function
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involved in a novel pathway for pyruvate dissimilation (GAS pathway: utilizes the glyoxylate shunt, anaplerotic fixation of carbon from CO2 and succinyl CoA synthetase for the generation of succinyl CoA)
physiological function
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involved in a novel pathway for pyruvate dissimilation (GAS pathway: utilizes the glyoxylate shunt, anaplerotic fixation of carbon from CO2 and succinyl CoA synthetase for the generation of succinyl CoA)
physiological function
-
isocitrate lyase plays a key role for survival of Mycobacterium tuberculosis in the latent form during a chronic stage of infection. The enzyme is important during steady stage growth when it converts isocitrate to succinate and glyoxylate
physiological function
isocitrate lyase plays an important role in the ability of Pseudomonas aeruginosa to grow on fatty acids, acetate, acyclic terpenes, and amino acids
physiological function
-
key enzyme of the glyoxylate cycle
physiological function
-
Mycobacterium tuberculosis isocitrate lyases are catalytically bifunctional isocitrate and methylisocitrate lyases required for growth on even and odd chain fatty acids
physiological function
-
the enzyme catalyzes the first committed step in the glyoxylate cycle, it is essential in Mycobacterium tuberculosis for cell survival during chronic infection
physiological function
-
the enzyme regulates the type III secretion system, T3SS, overview. Expression of the T3SS in oxygen-limited growth conditions is strongly dependent on the glyoxylate shunt enzyme, isocitrate lyase, which probably affects the RetS/LadS signalling pathways. ICL-dependent regulation of the T3SS does not alter the expression level of the master transcriptional regulator, ExsA, but affects expression of the T3 structural proteins, effectors and regulators, ExsC, ExsD and ExsE
physiological function
isocitrate lyase is a key enzyme of the glyoxylate shunt crucial for the survival of Mycobacterium tuberculosis in macrophages during persistent infection
physiological function
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the enzyme plays a key role during Puccinia striiformis f. sp. tritici germination
physiological function
-
the enzyme plays a key role during Puccinia striiformis f. sp. tritici germination
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physiological function
-
the enzyme catalyzes the first committed step in the glyoxylate cycle, it is essential in Mycobacterium tuberculosis for cell survival during chronic infection
-
physiological function
-
involved in a novel pathway for pyruvate dissimilation (GAS pathway: utilizes the glyoxylate shunt, anaplerotic fixation of carbon from CO2 and succinyl CoA synthetase for the generation of succinyl CoA)
-
physiological function
-
isocitrate lyase is a key enzyme of the glyoxylate shunt crucial for the survival of Mycobacterium tuberculosis in macrophages during persistent infection
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physiological function
-
ICL gene is required for non-growing survival in the Loebel model (nutrient deprivation in oxygen-rich medium)
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physiological function
-
key enzyme of the glyoxylate cycle
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additional information
conserved residues in the subfamily 3 signature of ICL-Pa play important roles in catalysis and thermostability and are likely associated with the catalytic loop structural conformation. Three-dimensional structural homology modeling of ICL-Pa wild-type and mutants, structure comparisons, active site modeling, overview. Residue N214 plays an essential role in ICL-Pa catalytic activity
additional information
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conserved residues in the subfamily 3 signature of ICL-Pa play important roles in catalysis and thermostability and are likely associated with the catalytic loop structural conformation. Three-dimensional structural homology modeling of ICL-Pa wild-type and mutants, structure comparisons, active site modeling, overview. Residue N214 plays an essential role in ICL-Pa catalytic activity
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