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Information on EC 4.1.3.1 - isocitrate lyase
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4.1.3.1 isocitrate lyaseIUBMB Comments
The isomer of isocitrate involved is (1R,2S)-1-hydroxypropane-1,2,3-tricarboxylate .
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Word Map
- 4.1.3.1
-
interstrand
- malate
- lens
- eyes
-
collamer
-
crosslinks
-
postoperative
-
intraocular
-
refract
-
fanconi
-
acuity
- anemia
-
preoperative
-
phakic
-
posterior
-
uncorrected
-
spherical
-
myopic
-
vault
-
fork
- corneal
-
diopter
-
fancd2
- glyoxysomal
- lymphocytopenia
- astigmatism
- mitomycin
-
pupil
-
logmar
-
translesion
- psoralens
- microbodies
-
monoubiquitination
-
anaplerotic
-
lasik
-
keratomileusis
-
pupillary
-
hyperopic
- rad51
-
monoadducts
-
gaba-induced
-
incisions
-
subcapsular
-
biomicroscopy
- itaconate
- molecular biology
- medicine
-
snellen
- drug development
-
vision-threatening
-
best-corrected
- gelatinosa
- sn-glycerol-3-phosphate
The enzyme appears in viruses and cellular organisms
Synonyms
icl, isocitrate lyase, citrate lyase, mtbicl, eggce, isocitritase, isocitratase, isocitric lyase, fpicl1, petal death protein, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AceA
acuD
citrate lyase
EgGCE
FPICL1
ICL
ICL1
ICL2
isocitrate lyase
isocitrate lyase 1
isocitrate lyase 2
SSO1333
ICL
-
-
ICL1
isoenzyme, has both isocitrate lyase and 2-methylisocitrate lyase activity
ICL1
isoenzyme, has both isocitrate lyase and 2-methylisocitrate lyase activity
isocitrate lyase
activity of a bifunctional protein named glyoxylate cycle enzyme (malate synthase and isocitrate lyase activity)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
isocitrate = succinate + glyoxylate
-
-
-
-
isocitrate = succinate + glyoxylate
kinetic mechanism is the same in microgravity and in standard g controls
-
isocitrate = succinate + glyoxylate
common mechanism for catalysis with succinate: (1) an unfavorable prebinding isomerization of the active site Cys191-His193 pair to the thiolate-imidazolium form, a process that is favored in D2O, and (2) the transfer of a proton from succinate or 3-NP to Cys191
-
isocitrate = succinate + glyoxylate
common mechanism for catalysis with succinate: (1) an unfavorable prebinding isomerization of the active site Cys191-His193 pair to the thiolate-imidazolium form, a process that is favored in D2O, and (2) the transfer of a proton from succinate or 3-NP to Cys191
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
isocitrate glyoxylate-lyase (succinate-forming)
The isomer of isocitrate involved is (1R,2S)-1-hydroxypropane-1,2,3-tricarboxylate [3].
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CAS REGISTRY NUMBER
COMMENTARY
9045-78-7
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1S,2S)-1-hydroxypropane-1,2,3-tricarboxylate
succinate + glyoxylate
-
reversible aldol cleavage
glyoxylate shunt
r
(2R)-ethyl-(3S)-methyl malate
2-oxobutanoate + propanoate
-
-
?
(2R)-isobutyl-(3S)-methyl malate
4-methyl-2-oxopentanoate + propanoate
-
-
?
(2R)-propyl-(3S)-methyl malate
4-methyl-2-oxopentanoate + propanoate
-
-
?
isocitrate + phenylhydrazine
? + glyoxylate phenylhydrazone
-
-
-
?
(2R,3S:2S,3R)-2-methyl-isocitrate
succinate + pyruvate
-
-
?
(2R,3S:2S,3R)-2-methyl-isocitrate
succinate + pyruvate
-
-
?
isocitrate
?
-
assimilation of one-carbon compounds in the icl+ serine pathway
-
?
isocitrate
glyoxylate + succinate
-
blue-native SDS-PAGE
coupling glyoxylate formation to lactate dehydrogenase type II activity (10 U) in presence of NAD+
?
isocitrate
succinate + glyoxylate
-
pH 7.3, cell-free extracts, in presence of MgCl2 and 2,4-dinitrophenylhydrazine
analysis based on absorbance at 450 nm
?
isocitrate
succinate + glyoxylate
-
pH 7.3, cell-free extracts, in presence of MgCl2 and 2,4-dinitrophenylhydrazine
analysis based on absorbance at 450 nm
?
isocitrate
succinate + glyoxylate
-
first step in glyoxylate-bypass pathway
-
?
isocitrate
succinate + glyoxylate
-
regulatory enzyme playing a crucial role in fungal growth
-
?
isocitrate
succinate + glyoxylate
-
key enzyme of the glyoxylate cycle
-
?
isocitrate
succinate + glyoxylate
-
key enzyme of the glyoxylate cycle
-
?
isocitrate
succinate + glyoxylate
-
-
-
?
isocitrate
succinate + glyoxylate
-
30°C, pH 7.5, HEPES containing phenylhydrazine HCl
absorbance of glyoxylate phenylhydrazone at 334 nm
r
isocitrate
succinate + glyoxylate
-
isotopic analysis, solvent kinetic isotope effects in the direction of isocitrate cleavage arise from the initial deprotonation of the C2 hydroxyl group of isocitrate or the protonation of the aci-acid of the succinate product of the isocitrate aldolcleavage by a solvent-derived proton, equilibrium perturbation in D2O, NMR spectroscopy and mass spectrometry, modeling, overview. The final equilibrium isotopic composition of reactants in D2O reveals dideuterated succinate, protiated glyoxylate, and monodeuterated isocitrate, with the transient appearance and disappearance of monodeuterated succinate
-
r
isocitrate
succinate + glyoxylate
-
-
?
isocitrate
succinate + glyoxylate
-
rate-limiting enzyme of the citric acid cycle
-
?
isocitrate
succinate + glyoxylate
-
first enzyme of glyoxylate shunt
-
?
threo-DL-isocitrate
succinate + glyoxylate
-
-
?
additional information
?
-
-
Lys-193, Cys-195, His-197 and His-356 are catalytic, active-site residues, while His-184 is involved in the assembly of the tetrameric enzyme
-
?
additional information
?
-
-
Mycobacterium tuberculosis isocitrate lyases are catalytically bifunctional isocitrate and methylisocitrate lyases, EC 4.1.3.1 and EC 4.1.3.30, required for growth on even and odd chain fatty acids
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1S,2S)-1-hydroxypropane-1,2,3-tricarboxylate
succinate + glyoxylate
-
reversible aldol cleavage
glyoxylate shunt
-
r
additional information
?
-
-
Mycobacterium tuberculosis isocitrate lyases are catalytically bifunctional isocitrate and methylisocitrate lyases, EC 4.1.3.1 and EC 4.1.3.30, required for growth on even and odd chain fatty acids
-
-
?
isocitrate
?
-
assimilation of one-carbon compounds in the icl+ serine pathway
-
-
?
isocitrate
succinate + glyoxylate
-
first step in glyoxylate-bypass pathway
-
?
isocitrate
succinate + glyoxylate
-
regulatory enzyme playing a crucial role in fungal growth
-
?
isocitrate
succinate + glyoxylate
-
key enzyme of the glyoxylate cycle
-
-
?
isocitrate
succinate + glyoxylate
-
key enzyme of the glyoxylate cycle
-
-
?
isocitrate
succinate + glyoxylate
-
-
-
-
?
isocitrate
succinate + glyoxylate
-
rate-limiting enzyme of the citric acid cycle
-
?
isocitrate
succinate + glyoxylate
-
first enzyme of glyoxylate shunt
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ba2+
Cd2+
-
5 mM, 90% inhibition of Mg2+-activated enzyme, interaction with catalytic domain induces partial unfolding (revealed by thermal denaturation, far-UV circular dichroism, fluorescence spectra, and glutaraldehyde crosslinking)
Co2+
Fe2+
Mg2+
Mn2+
Ni2+
Sr2+
Zn2+
-
5 mM, 90% inhibition of Mg2+-activated enzyme, interaction with catalytic domain induces partial unfolding (revealed by thermal denaturation, far-UV circular dichroism, ANS fluorescence spectra, and glutaraldehyde crosslinking)
additional information
Fe2+
-
no activity in absence of exogenous cation, Fe2+ 7% as effective as Mg2+
Mg2+
-
requirement, optimal concentration: 2 mM, Km value: 0.092 at pH 7
Mg2+
-
required, in the absence of Mg2+, no enzymatic activity is measured
Mg2+
-
Icl enzyme: most effective cation, optimal concentration: 5 mM
Mg2+
-
5 mM, essential for catalytic activity, 100% activity, binds and stabilizes non-catalytic alpha/beta barrel core without structural alterations (revealed by thermal, urea and GdnHCL denaturation and far-UV CD)
Mg2+
-
reactivation after thermal inactivation, Mg2+-isocitrate complex is true substrate, 2 Mg2+-binding sites: catalytic and activator site
Mn2+
-
Icl enzyme: can replace Mg2+, yielding 39% of the activity obtained with Mg2+
Mn2+
-
5 mM, 45% activity, binds and stabilizes non-catalytic alpha/beta barrel core without structural alterations (revealed by thermal, urea and GdnHCL denaturation and far-UV CD)
Ni2+
-
no activity in absence of exogenous cation, Ni2+ 7% as effective as Mg2+
Sr2+
-
no activity in absence of exogenous cation, Sr2+ 3% as effective as Mg2+
additional information
-
isoform ICL2 is not activated by Mg2+. Ca2+and K+ reveal no marked effect on both isoforms of the enzyme
additional information
-
no significant change in enzyme activity after incubation with Co2+, Pb2+, Fe2+, Cu2+, Cd2+, Na+, K+, Cl-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(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.
(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
-
-
(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.
1-(5-hydroxy-1H-indol-3-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione
i.e. hyrtiosin B
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-hydroxyheteronemin
-
cytotoxic, isolated from Smenospongia sp.
2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenylmethane
-
-
2,5-dichloro-3-[(3E)-4-chloro-3-methylbut-3-en-1-yn-1-yl]-6-hydroxycyclohexa-2,5-diene-1,4-dione
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-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol
-
-
3-nitro-1-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-one
-
-
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-[[1-(4-chlorophenyl)-5-(6-methoxynaphthalen-2-yl)-3-oxopentyl]amino]benzoic acid
-
-
5-bromo-2-[[4-(trifluoromethyl)phenyl]carbamoyl]phenyl N-prop-1-en-2-yl-L-phenylalaninate
-
-
5-chloro-2-[[4-(trifluoromethyl)phenyl]carbamoyl]phenyl pyrazine-2-carboxylate
-
-
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
-
-
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
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.
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
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
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
-
[(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-(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
-
-
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
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-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-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-methoxybenzothioamide
-
-
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-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-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-methoxybenzothioamide
-
-
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
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
Itaconate
-
a succinate analogue lacking an acidic alpha-proton, the inhhibitor does not display slow-binding behavior
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
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
-
p-chloromercuribenzoate
-
100% inhibition at 0.02 mM, reversible by 2-mercaptoethanol
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
-
halisulfates from the tropical sponge Hippospongia sp. are able to inhibit ICL activity, appressorium formation and C2 utilization
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
acetate
-
activity of the ICL promoter is significantly upregulated during growth on acetate
glutaredoxin 1
-
reactivation of GSSG-treated ICL in the presence of glutaredoxin 1 within 20 min
-
acetyl-CoA
more than 4fold increased enzyme activity in the presence of 150 microM acetyl-CoA
acetyl-CoA
increases the substrate binding affinities isocitrate and succinate, but had little effect on the affinity for glyoxylate
additional information
-
high enzymic activity of ICL in strains isolated from diabetic patients suffering from vulvovaginal candidiasis. Specific activation of ICL1 when the pathogen is exposed to neutrophils or macrophages
-
additional information
-
no reactivation of GSSG-treated ICL in the presence of thioredoxin 1
-
additional information
-
no evidence that isocitrate lyase contains coenzyme
-
additional information
-
no evidence that isocitrate lyase contains coenzyme
-
additional information
-
no evidence that isocitrate lyase contains coenzyme
-
additional information
-
no evidence that isocitrate lyase contains coenzyme
-
additional information
-
ICL activity increases in pellicles in synthetic media as a consequence of fatty acid degradation as well as under microaerophilic growth conditions
-
additional information
-
no significant change in enzyme activity after incubation with serine, glycine, aspartic and glutamic acids
-
additional information
-
no evidence that isocitrate lyase contains coenzyme
-