Ligand indole-3-acetic acid

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Basic Ligand Information

Molecular Structure
Picture of indole-3-acetic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H9NO2
indole-3-acetic acid
SEOVTRFCIGRIMH-UHFFFAOYSA-N
Synonyms:
(1H-indol-3-yl)acetate, (indol-3-yl)acetate, (indol-3-yl)acetic acid, 3-indolacetate, 3-indole acetic acid, 3-indoleacetic acid, 3-indolylacetic acid, auxin, beta-indolylacetic acid, IAA, indol-3-acetic acid, indol-3-yl acetic acid, indole-3-acetate, indole-3-acetic-acid, indole-acetic acid, indole 3-acetic acid, indoleacetate, indole acetate, indoleacetic acid, indole acetic acid


Show all pahtways known for Show all BRENDA pathways known for indole-3-acetic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + (indol-3-yl)acetate = S-adenosyl-L-homocysteine + methyl (indol-3-yl)acetate
show the reaction diagram
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(1H-indol-3-yl)acetate = skatole + CO2
show the reaction diagram
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ATP + indoleacetate + L-Lys = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
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indole-3-acetic-acid-L-alanine + H2O = indole-3-acetic-acid + L-alanine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
indole-3-acetate + NADH + H+ + O2 = ?
show the reaction diagram
(indol-3-yl)acetate + NADH + H+ + O2 = (2-hydroxyindol-3-yl)acetate + NAD+ + H2O
show the reaction diagram
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indoleacetate + NAD(P)H + O2 + H+ = 5-hydroxyindoleacetate + NAD(P)+ + H2O
show the reaction diagram
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indole-3-acetic acid + FADH2 + chloride + O2 + H+ = 5-chloroindole-3-acetic acid + FAD + 2 H2O
show the reaction diagram
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S-adenosyl-L-methionine + (indol-3-yl)acetate = S-adenosyl-L-homocysteine + methyl (indol-3-yl)acetate
show the reaction diagram
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dimethylallyl diphosphate + indole-3-acetic acid = diphosphate + 7-(3-methylbut-2-enyl)-indole-3-acetic acid
show the reaction diagram
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succinyl-CoA + indole-3-acetate = succinate + indole-3-acetyl-CoA
show the reaction diagram
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(1H-indol-3-yl)acetate = skatole + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
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indole-3-acetaldehyde + NAD+ + H2O = indole-3-acetate + NADH + H+
show the reaction diagram
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indole-3-acetaldehyde + NAD+ + H2O = indole-3-acetate + NADH + H+
show the reaction diagram
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indoleacetaldehyde + NAD+ + H2O = indoleacetate + NADH
show the reaction diagram
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indole-3-acetaldehyde + NAD+ + H2O = indole-3-acetate + NADH + H+
show the reaction diagram
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indole-3-acetaldehyde + NAD+ + H2O = indole-3-acetate + NADH + H+
show the reaction diagram
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indole 3-acetaldehyde + H2O + O2 = indole 3-acetic acid + H2O2
show the reaction diagram
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indoleacetaldehyde + H2O + oxidized benzyl viologen = indoleacetate + H+ + reduced benzyl viologen
show the reaction diagram
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Indoleacetaldehyde + benzyl viologen = Indoleacetate + reduced benzyl viologen
show the reaction diagram
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indoleacetaldehyde + 2,6-dichlorophenolindophenol + H2O = indoleacetate + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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ADP + phosphate + indoleacetyl-CoA = ATP + indoleacetate + CoA
show the reaction diagram
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ADP + phosphate + indole-3-acetyl-CoA = ATP + indole-3-acetate + CoA
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation up to 0.05 mM
-
0.1 mM, increases level of ACO2 transcript in vivo, not ACO1
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activation of phosphorolysis
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the phytohormone increases specific activity of the enzyme practically during the entire growing period, except for the youngest leaves
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The expression of AtIpk2b is enhanced in roots after treatment with 1 microM. Expression of AtIpk2b become stronger when the concentration of exogenous indole-3-acetic acid is increased to 10 microM. By treatment with 40 microM, AtIpk2b expression increases after 0.5 h of treatment, whereas the expression of AtIpk2a remains virtually unaffected. These results indicate that AtIpk2b is an IAA-inducible gene, while AtIpk2a is not.
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enhances activity of both gly I and II
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stimulates
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expression of ipdC is upregulated by indole-3-acetic acid, other auxins, and nutrient stress
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upregulates CAS expression
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activates enzyme activity
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Inhibitor in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibitory above 0.05 mM
-
non-competitive inhibition
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1 mM, 19% inhibition of cleavage of D-tryptophan, 27% inhibition of cleavage of L-tryptophan
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auxin hormone from seeds decreases PsGA2ox1 mRNA levels 2 h after application to deseeded pericarps, sharply increases after 4 h and stays elevated
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feedback inhibition in vivo
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42% inhibition with tyrosine at 3 mM and indole-3-acetic acid at 12 mM
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weak
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GMP + ATP protect
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either in tobacco PG or wild-type plants treated with oligogalacturonides, resistance to fungal infection is suppressed by exogenous auxin, whereas sensitivity to auxin of PG plants is reduced in different bioassays. Altered auxin sensitivity in PG plants may be due to an increased accumulation of oligogalacturonides and subsequent antagonism of auxin action
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competitive inhibition, Ki: 1.14 mM
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slight
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affects specifically MPP, less effective than NEM or PCMB, dithioerythritol protects
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the plant hormone decreases enzyme activity in hearts, but not in kidney and muscle
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3.5 mM, 50% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2.27
-
pH 7.6, 30C
66
-
isoenzyme ACS II
3.45
-
pH 8.0, 55C

KM Value (10 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
64
-
-
1.24
-
pH 8.0, 55C

Ki Value (5 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.6
-
non-competitive inhibition
2.7
-
-
0.07
-
-
0.078
-
-
3.5
-
-

References & Links

Links to other databases for indole-3-acetic acid

ChEBI
PubChem
ChEBI
PubChem