Ligand Itaconate

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Basic Ligand Information

Molecular Structure
Picture of Itaconate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H6O4
Itaconate
QBKSWRVVCFFDOT-UHFFFAOYSA-N
Synonyms:
2-methylenesuccinic acid, 2-methylidenebutanedioic acid, Itaconic acid, methylenesuccinate, Methylene succinate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + itaconate + CoA = ADP + phosphate + itaconyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-aconitate = itaconate + CO2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-methylenesuccinic acid + NAD(P)H = (R)-2-methylsuccinic acid + NAD(P)+
show the reaction diagram
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S-adenosyl-L-methionine + itaconate = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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succinyl-CoA + itaconate = succinate + ?
show the reaction diagram
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succinyl-CoA + itaconate = succinate + ?
show the reaction diagram
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itaconate + succinyl-CoA = ? + succinate
show the reaction diagram
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itaconate = methylmaleate
show the reaction diagram
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GTP + itaconate + CoA = GDP + phosphate + itaconyl-CoA
show the reaction diagram
-
ATP + itaconate + CoA = ADP + phosphate + itaconyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-aconitate = itaconate + CO2
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates even in the presence of 10 mM 2-oxoglutarate
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Inhibitor in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
18% inhibition at 5 mM
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competitively inhibited by di-and tricarboxylic acids, itaconic acid being most effective, monocarboxylic acids do not inhibit
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competitive, most effective inhibitor, Ki: 0.74 mM
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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 propionat-grown cells, not in acetate-grown cells
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IC90 (compound concentration at which 90% or higher inhibition is observed) 10 microM, using high-throughput screen, relaxation inhibition 100%
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2
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KM Value (7 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
44
-
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60
-
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Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.8
-
-
0.74
-
competitive, most effective inhibitor

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.06
-
-

References & Links

Links to other databases for Itaconate

ChEBI
PubChem
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PubChem