Ligand iodoacetic acid

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Basic Ligand Information

Molecular Structure

C₂H₃IO₂

iodoacetic acid

JDNTWHVOXJZDSN-UHFFFAOYSA-N

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Synonyms:

2-Iodoacetate, 2-iodoacetic acid, CH2ICOOH, ICH2COOH, iodacetic acid, iodoacatate, iodoacetate, monoiode acetate, monoiodoacetate, mono iodoacetate, Monoiodoacetic acid, monoiodo acetic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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3.8.1.2

2 entries

3.8.1.3

monoiodoacetate + H2O = glycolate + HI

210644

Substrate in Enzyme-catalyzed Reactions (6 results)

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3.8.1.10

monoiodoacetate + H2O = glycolate + HI

monoiodoacetate + H2O = glycolate + HI

210644

Product in Enzyme-catalyzed Reactions (4 results)

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3.1.1.1

ethyl iodoacetate + H2O = ethanol + iodoacetate

3.5.1.14

2 entries

3.5.1.17

N6-iodoacetyl-L-lysine + H2O = L-lysine + iodoacetate

Activator in Enzyme-catalyzed Reactions (31 results)

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1.1.1.1

1 mM, 1.1fold activation

688442

1.1.1.283

activation of enzyme MGR I, inhibition of enzyme MGR II

activity 102.5%

stimulation

112% activity at 10 mM

activation

activation

10% activation at 5 mM

680948

3.1.3.26

0.1 mM, 28% activation. The enzyme may be a 3-phytase, EC 3.1.3.8, or a 6-phytase, EC 3.1.3.26. The product of the hydrolysis of myo-inositol hexakisphosphate i.e. myo-inositol 1,2,3,4,5-pentakisphosphate or myo-inositol 1,3,4,5,6-pentakisphosphate has not been identified

665933

3.1.3.8

0.1 mM, 28% acti1vation. The enzyme may be a 3-phytase, EC 3.1.3.8, or a 6-phytase, EC 3.1.3.26. The product of the hydrolysis of myo-inositol hexakisphosphate i.e. myo-inositol 1,2,3,4,5-pentakisphosphate or myo-inositol 1,3,4,5,6-pentakisphosphate has not been identified

665933

3.1.4.4

rapid induction of isoform PLDbeta1

679111

3.2.1.151

induction in green seedling

680027

3.2.1.4

5 mM, 105% of initial activity

735843

3.2.1.55

1 mM, relative activity 102.7%

288826

3.2.1.8

activation of isozymes Ic and IIB

654986

3.2.1.93

1 mM, activation to 103.26% of control, rTRE_P3

771475

3.4.11.21

0.1 mM, 1.8fold activation

771201

3.4.24.37

11% activation at 1 mM

683560

3.5.4.3

1mM, relative activity 103%

209539

3.5.4.5

0.10 mM, activity 105%

10 mM, stimulates

0.1 mM, 53% increase in activity

activates

activates up to 80% by low concentrations, in a 1:1 molar ratio with the 40000 MW species of the enzyme

680

7.1.2.1

in roots in low-phosphorus nutrient solution, iodoacetic acid stimulates the activity of plasma membrane H+-ATPase and phosphorus uptake. The effect is blocked by naphthylphthalamic acid

688069

Inhibitor in Enzyme-catalyzed Reactions (960 results)

1 mM, 50% inhibition after 14 min, half-inactivation time increases to 29.0 min in the presence of 20 mM D-pantoate, 70% inhibition within 50 min at pH 7.2, 20 mM pantoate decreases inactivation from 70 to 30%

strong inhibition

10% inhibition at 1 mM

85% inhibition at 1 mM

285940

1.1.1.144

10 mM, 95% inhibition, prevented by 10 mM glutathione

70% remaining activity at concentration 1 mM

286085

1.1.1.165

complete inhibition at 2 mM

sulfhydryl reagents, slightly inhibitory

62% inhibition at 10 mM

1 mM, 56% residual activity

42% inhibition of oxidation and 19% inhibition of reduction at 10 mM

347839

1.1.1.201

complete inhibition at 0.05 mM

50% inhibition at 0.1 mM

to some extent

slight inhibition

complete inhibition at 10 mM

389504

1.1.1.244

weak inhibition of aldehyde reduction

27% inhibition at 1 mM

1 mM, 16.4% residual activity

weaker inhibitor than p-chloromercuribenzoate or HgCl2

weak inhibition

1 mM, 49% inhibition

weak

1 mM, 29% inhibition with NAD+ as cofactor, 80% with NADP+ as cofactor

more inhibitory in intact cells than in cell free extracts

isoenzyme 2, 1 mM, 97% inhibition, isoenzyme 1, 1 mM, 18% inhibition

94.5% residual activity at 10 mM

5% inhibition at 1 mM

10% inhibition at 1 mM

724598

1.1.3.2

33% inhibition at 1 mM

440395

1.1.3.21

1 mM, less than 20% inhibition

44% inhibition at 2 mM

287628

1.1.3.6

1 mM, 30 min at 4°C, 15% inhibition

63% residual activity at 1 mM

1 mM, 17.4% inhibition

10899

1.1.99.32

4.2 mM, 34% inhibition

677427

1.1.99.37

less than 10% inhibition at a concentration of 5 mM

286374

1.10.3.1

1 mM; 1 mM: 46%, 39% and 31% inhibition of isoenzymes Ia, Ib, and II, respectively

0.0005 mM, 19% inhibition

weak

preincubation with substrate protects against inactivation

439515

1.13.11.29

55% inhibition at 0.1 mM

55% inhibition at 0.1 mM

1 mM, 5% inhibition

5 mM 30 min

1 mM, 12% inhibition of cleavage of D-tryptophan, 7% inhibition of cleavage of L-tryptophan

cysteine-directed reagent, 1 mM, 42% inhibition

649382

1.13.11.74

40% residual activity at 0.5 mM

1 mM, complete inhibition

less effective than p-chloromercuriphenylsulfonate

10 mM, 50% inhibition of ferredoxinNAP reductase

437842

1.14.12.13

55% inhibition at 2 mM

439074

1.14.12.16

2 mM, complete loss of activity

7068

1.14.12.9

0.01 mM, 77% inhibition

partial inhibition

at 1 mM 100% inhibition of 17alpha-hydroxylation and 50% inhibition of lyase activity

287096

1.14.14.21

46% inhibition at 1 mM

5 mM, 23% inhibition

weak

DELTA12-desaturase system, enzymatic complex

inhibition reversed by addition of GSH or cysteine

390584

1.15.1.1

23.5% inhibition at 1 mM

704820

1.17.1.4

21% inhibition at 1 mM

10 mM, 50% inhibition

437842

1.18.1.7

50% inhibition at 10 mM

potent inhibitor

preincubation with glyceraldehyde-phosphate, 10fold molar excess over iodoacetate, prevents inactivation

slowly

1 mM, isozymes A, 83% inhibition, isozyme C, 100% inhibition

inhibition of the reduction of benzoyladenosine 5'-monophosphate, even in the presence of dithiothreitol

288180

1.2.1.32

31% inhibition at 1 mM; 69% remaining activity at an inhibitor concentration of 1 mM

672682

1.2.1.39

18% inhibition in the presence of 1 mM

15% inhibition at 1 mM

69% residual activity at 1 mM

672682

1.2.3.1

31% inhibition at 1 mM

23°C, in a concentration-dependent manner

644696

1.2.7.B2

5 mM, 50% inhibition after min

5 mM, complete inhibition

11936

1.20.4.1

inactivates wild type enzyme and mutant enzyme C106S, in presence of substrate, arsenate, or the competitive inhibitors phosphate or sulfate, the rate of the alkylation is reduced

639365

1.20.4.4

sulfhydryl inhibitors N-ethylmaleimide -and iodoacetate inhibit arsenate reductase activity by 80% in crude cell-free preparations and by 90% with purified ArsC protein

the ability of protein component C to catalyse the arsenate-dependent decomposition of acetyl phosphate is inhibited, but protein C is protected from inactivation by treatment acetyl phosphate

636469, 636473

1.21.99.3

recombinant and native isozyme type III

3.3 mM, 29% inhibition

390510

1.3.1.116

1.0 mM, 9% inhibition

745196

1.3.1.12

390522, 390537, 390542

inhibition of 70-80% at concentration of 1 mM

1 mM, 34% inhibition

slight inhibition

slight inhibition

50% inhibition of apoenzyme at 2 mM, not inhibitory for the holo form

1 mM, 8% inhibition

50 mM, partial

weak

1 mM, 30°C, 15% loss of aminating activity

81.6% residual activity at 1 mM

724793

1.4.3.7

68% inhibition at 0.1 mM

395288

1.4.5.1

0.1 mM, 62% inhibition

15% inhibition at 1 mM

10% inactivation at 1 mM

392127

1.5.1.36

1.0 mM, 9% inhibition

complete inhibition at 1 mM

394961

1.5.3.20

2 mM, 28% residual activity

3 mM

64% inhibition

progressive inhibition, 2 mM GMP protect

partial

low effect

in presence of NADH or dihydrolipoamide

0.054 mM, 57% inhibition

1 mM, 19% inhibition

1 mM, 51% residual activity

740640

1.8.2.5

0.5 mM, 70% inhibition

complete inhibition at 10 mM

complete inhibition at 100 mM, 79% inhibition at 10 mM

670507

2.1.1.160

complete inhibition at 100 mM, 89% inhibition at 10 mM

670507

2.1.1.165

5 mM, 28% inhibition, production of methyl iodide

slight inhibition

weak

441507, 441509, 441533

83% inhibition at 3.3 mM

inhibition at 0.5 mM

76% inactivation after 4 min at 5 mM

5 mM, complete inhibition

0.01 mM, 71% inhibition

488137

2.3.3.18

1 mM, 18% residual activity

740585

2.3.3.9

5 mM, 6% residual activity

weak inhibition

0.2 mM inhibits the enzyme 70%

0.001-0.01 mM: 50-70% inhibition

30% inhibition at 1 mM

1 mM, 47% inhibition

10 mM, 84% activity retains

slight inhibition

98.9% inhibition at 25 mM

735987

2.4.1.68

10 mM, 35% inhibition

1 mM, 91% inhibition

489559, 489566, 489572

1 mM, complete inactivation

0.5 mM, 24% inhibition

1 mM, 75% inhibition

0.004 M, 95% inhibition

637142

2.7.1.14

60% inhibition at 10 mM

1 mM, 56% inhibition of the 63000 Da isoform, no inhibition of the 410000 Da isoform

0.1 mM, complete loss of activity

1 mM, 41% inhibition

5 mM, 87% inhibition, NADH protects

642389, 642394, 642399

1.67 mM, 12% inhibition

642495

2.7.4.14

0.05 mM, 50% inhibition

DNA polymerase beta

1 mM, 42% remaining activity

645513, 645515, 645518

2.8.1.2

662415, 723958

2.8.2.14

645709, 645712, 645714, 645720

weak inhibition

slight inhibition

48% residual activity at 1 mM

plasmalogen-specific PLA2

1 mM inhibits 5% of the activity

80982, 80985, 80987

69% inhibition of D-glucose 1-phosphate hydrolysis by 10 mM

50 mM, 30% inhibition after 1 h at 30°C

30% inhibition at 10 mM

114218

3.1.3.26

70% inhibition at 1 mM

95% inhibition at 1 mM

monoiodoacetic acid, 1 mM, weak

135991

3.2.1.115

still 60.1% relative activity

weak inhibition

1 mM, about 80% inhibition

93% residual activity at 1 mM

30.33% residual activity at 10 mM

inhibition of beta-xylosidase A

strong inhibition

34% inhibition at 5 mM

1 M, 10% loss of activity

750928

3.2.1.50

complete inhibition at 2.5 mM

208693

3.2.1.52

with 1 mM 73% of activity remains

5 mM, 34% inhibition

79.7% residual activity at 5 mM

5 mM, 17% inhibition

5 mM, 3% inhibition of 2-nitrophenyl beta-D-galactopyranoside hydrolysis, no inhibition of 4-nitrophenyl beta-D-glucopyranoside hydrolysis

725057

3.2.2.1

0.01 M, 25% inhibition. 0.02 M 36.1% inhibition

326387

3.3.2.2

12 mM, 17% inhibition

weak

1 mM, 11% inhibition

25% inhibition at 1 mM

0.1 mM, complete inactivation

inhibition of wild-type but not of S120C mutant

1.0 mM inhibitor, 25% inhibition, 5.0 mM inhibitor, 48% inhibition

90% inhibition

1 mM, 38% inhibition

25% inhibition at 1 mM

1 mM, 16.5% inhibition; 16.5% inhibition at 1 mM

3 mM inhibits at pH 7.5 with casein as a substrate and at pH 3.5 with bovine serum albumin as a substrate

1 mM, 10% inhibition

5 mM, 17% inhibition

1 mM, 92% inhibition

0.4 mM, complete inhibition

5% residual activity at 2 mM

1 mM, 76% inhibition

0.05 mM, 80% inhibition

0.25 mM, complete

exceptionally low rat constant for inhibition

weak inhibitor

1 mM, 22% inhibition

3 mM,88 % inhibition

83% inhibition

affects specifically MPP, less effective than NEM or PCMB, dithioerythritol protects

1.0 mM, 54.04 mM inhibition

1 mM, 40% inhibition

55% inhibition at 0.25 mM

740655

3.5.1.137

13% residual activity at 1 mM

1 mM, 73% inhibition

with 20 micromol iodoacetate the activity is 33% after 10 min

2.5 mM, 55% inhibition

weak

weak

1 mM: strong inhibition

172071

3.5.1.65

2 mM: strong inhibition, protected partially, about 30%, by preincubation, 15 min, with 20 mM 2-mercaptoethanol

209221

3.5.1.71

4 mM: 100% inhibition

209230

3.5.1.73

1 mM, 28% loss of activity

288939

3.5.1.75

0.1 mM: 40% inhibition

weak

31906, 31907, 31908

16% residual activity at 5 mM for IsoI and 13% residual activity at 5 mM for IsoII

689405

3.5.3.11

the enzyme is rendered inactive when the purified enzyme is incubated with dithiothreitol followed by excess iodoacetic acid

slight

10 mM, complete inhibition

slight inhibition at 1 mM

weak

0.01 mM: 5% of maximal activity

648214

3.5.5.7

5 mM, complete inhibition

670792

3.5.99.2

0.01 mM 42% inhibition

246761

3.6.1.1

209770, 209790, 209799

3.6.1.17

10 mM, 58.8% residual activity

733872

3.6.1.20

inhibitory above 10 mM

209942

3.6.1.41

10 mM, 58.8% residual activity

0.5 mM

pyridoxal phosphate protects

10 mM, 15% inhibition

1 mM, 64% remaining activity

poor inhibitor

68% inhibition at 16 mM, complete inhibition at 35 mM

1 mM, 11% inhibition

10% inhibition at 10 mM

46% inhibition at 5 mM; 50 mM, almost complete inhibition

1 mM, 97% inhibition

50 mM, 43% inhibition

inhibition after prolonged incubation

5698

4.2.1.55

0.01 M, 12% inhibition

2.5 mM, 90% inhibition

slight

weak

1 mM, 45% loss of activity

2 mM, 25% inhibition

1 mM, 94% inhibition

1 mM, 86% loss of activity

inhibition to a minor degree, completely reversible

134538, 134540, 134544, 134550

weak inhibition

12% inhibition at 1 mM

weak

10 mM, more than 95% inhibition

0.7 mM, 100% inhibition

2936, 2944, 2947

1 mM, 80% inhibition

irreversibly inactivates

589, 592

75 mM, 100% inhibition

1188, 1190, 1211

1 mM and above

specific reaction with subunit acyl carrier protein

685053

Metals and Ions (2 results)

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3.2.1.22

5 mM, 43% residual activity

741505

3.2.1.28

10 mM, activates 1.3fold

655271

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

Enzyme Kinetic Parameters

K_M Value (1 result)

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3.8.1.3

1.1

210644

K_i Value (5 results)

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1.2.1.12

0.145

30°C, pH 7.2

0.179

pH 6.3, 38°C

661292

IC₅₀ Value (7 results)

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1.18.1.7

pH and temperature not specified in the publication

437842

1.5.3.1

200

IC50 equal or less 200 mM, at pH 8.0 and 30°C

References & Links

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Show Reference (1134 entries)

Links to other databases for iodoacetic acid

Ligand iodoacetic acid

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

Substrate in Enzyme-catalyzed Reactions (6 results)

Product in Enzyme-catalyzed Reactions (4 results)

Activator in Enzyme-catalyzed Reactions (31 results)

Inhibitor in Enzyme-catalyzed Reactions (960 results)

Metals and Ions (2 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

Enzyme Kinetic Parameters

KM Value (1 result)

Ki Value (5 results)

IC50 Value (7 results)

References & Links

Literature References (1134)

Links to other databases for iodoacetic acid

K_M Value (1 result)

K_i Value (5 results)

IC₅₀ Value (7 results)