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Ligand acetoacetic acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

citric acid cycle, leucine metabolism, lysine metabolism, propanol degradation, tyrosine metabolism

KEGG

Butanoate metabolism, Lysine degradation, Microbial metabolism in diverse environments, Styrene degradation, Two-component system, Tyrosine metabolism, Valine, leucine and isoleucine degradation more

MetaCyc

2-deoxy-D-ribose degradation II, acetoacetate degradation (to acetyl CoA), acetone degradation I (to methylglyoxal), acetone degradation II (to acetoacetate), acetone degradation III (to propane-1,2-diol), D-carnitine degradation I, isopropanol biosynthesis (engineered), ketogenesis, ketolysis, L-carnitine degradation III, L-leucine degradation I, L-lysine fermentation to acetate and butanoate, L-tyrosine degradation I, mevalonate degradation, propene degradation, pyruvate fermentation to acetone, TCA cycle VI (Helicobacter) more

Show all BRENDA pathways known for acetoacetic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Natural Substrate (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.30

acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+

737912, 737914

3vdr, 3D-view

1.1.1.30

acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+

737912, 737914

6zzo, 3D-view

1.1.1.30

2 entries

1.8.1.5

2-mercaptoethanesulfonate + acetoacetate + NADP+ = 2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+

288639, 288637, 288638

-

2.8.3.5

succinyl-CoA + acetoacetate = ?

645972, 645971, 645988, 80975, 645984, 645982, 645991, 645992

-

2.8.3.5

succinyl-CoA + acetoacetate = succinate + acetoacetyl-CoA

676985, 663018, 705310, 694193, 660674, 661256, 703810, 705523, 660636, 672216, 724277, 724109, 723826, 676034, 690880, 695186

-

4.1.1.4

acetoacetate + H+ = acetone + CO2

650919, 653267, 746884, 726757, 726777, 748436

-

4.1.1.4

Acetoacetate = ?

4538, 4522

-

2.8.3.5

2 entries

4.1.1.4

2 entries

6.2.1.16

ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA

720477, 690593, 728335, 744249, 744226, 744906, 746014

-

In Vivo Product in Enzyme-catalyzed Reactions (18 results)

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Show Natural Product (18 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH

286540, 286524, 286526, 286512, 286513, 286519, 286516, 286518, 286520, 286521, 286522, 286529, 286533, 286536, 286514, 286517, 286525, 286527, 286528, 286530, 286535, 286538, 286542, 286543, 286523, 286531, 0, 286539, 286541, 286532, 286537, 286515, 286534

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH

286540, 286524, 286526, 286512, 286513, 286519, 286516, 286518, 286520, 286521, 286522, 286529, 286533, 286536, 286514, 286517, 286525, 286527, 286528, 286530, 286535, 286538, 286542, 286543, 286523, 286531, 0, 286539, 286541, 286532, 286537, 286515, 286534

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADH + H+ = acetoacetate + NAD+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADH + H+ = acetoacetate + NAD+

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.30

8 entries

1.1.99.24

(S)-3-hydroxybutanoate + 2-oxoglutarate = acetoacetate + (R)-2-hydroxyglutarate

0

-

1.8.1.5

2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH = 2-mercaptoethanesulfonate + acetoacetate + NADP+

0

-

1.8.1.5

2-oxopropyl-coenzyme M + CO2 + NADPH = coenzyme M + acetoacetate + NADP+

0

-

1.8.1.5

2 entries

2.3.1.247

(5S)-5-amino-3-oxohexanoate + acetyl-CoA = L-3-aminobutanoyl-CoA + acetoacetate

0

-

2.6.1.18

L-beta-amino-n-butyric acid + pyruvate = 3-oxo-n-butyric acid + alanine

0

-

2.8.3.8

acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA

0

-

2.8.3.9

butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate

643837, 643839, 643838

-

3.7.1.2

4-fumarylacetoacetate + H2O = acetoacetate + fumarate

289257, 0, 289247, 289240, 289245, 289241, 289242, 289246

1qco, 3D-view

4.1.3.4

(S)-3-Hydroxy-3-methylglutaryl-CoA = Acetyl-CoA + acetoacetate

0

-

6.4.1.6

acetone + CO2 + ATP + H2O = acetoacetate + AMP + phosphate

0, 349804

-

Substrate in Enzyme-catalyzed Reactions (26 results)

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Show Substrate (26 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.30

acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+

737912, 737914

3vdr, 3D-view

1.1.1.30

acetoacetate + NADH + H+ = (R)-3-hydroxybutanoate + NAD+

737912, 737914

6zzo, 3D-view

1.1.1.30

2 entries

1.1.1.45

acetoacetate + NADH = ? + NAD+

669147

-

1.13.11.50

3-oxobutanone + O2 = ?

636327, 657866

-

1.8.1.5

2-mercaptoethanesulfonate + acetoacetate + NADP+ = 2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+

288638, 288639, 288637

-

1.8.1.5

3-mercaptopropanesulfonate + acetoacetate + NADP+ = 2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+

288638

-

1.8.1.5

3-mercaptopropionate + acetoacetate + NADP+ = 3-(2-oxopropylthio)propionate + CO2 + NADPH + H+

288638

-

1.8.1.5

acetoacetate + H+ = acetone + CO2

288638

-

1.8.1.5

CO2 + acetoacetate = acetoacetate + CO2

288638

-

1.8.1.5

5 entries

2.3.1.247

beta-alanyl-CoA + acetoacetate = ?

3378

-

2.6.1.18

beta-alanine + acetoacetate = malonic semialdehyde + 3-aminobutanoate

288059

-

2.8.3.1

acetyl-CoA + acetoacetate = acetate + acetoacetyl-CoA

737535

-

2.8.3.18

acetoacetate + succinyl-CoA = succinate + acetoacetyl-CoA

692865

-

2.8.3.18

acetyl-CoA + acetoacetate = acetoacetyl-CoA + acetate

721675

-

2.8.3.18

succinyl-CoA + acetoacetate = acetoacetyl-CoA + succinate

721675, 692865

-

2.8.3.5

succinyl-CoA + acetoacetate = ?

645972, 645971, 645988, 80975, 645984, 645982, 645991, 645992

-

2.8.3.5

succinyl-CoA + acetoacetate = succinate + acetoacetyl-CoA

80975, 676985, 645977, 645991, 645992, 663018, 705310, 724424, 676034, 694193, 645974, 645975, 645976, 645987, 645994, 660674, 661256, 703810, 705523, 645972, 645973, 645978, 645971, 645988, 645995, 660636, 645967, 645969, 645970, 645979, 645986, 672216, 645980, 645983, 695186, 738807, 724277, 724109, 737420, 645968, 723826, 690880

-

2.8.3.9

acetyl-CoA + acetoacetate = acetate + acetoacetyl-CoA

643837

-

2.8.3.9

butanoyl-CoA + acetoacetate = butanoate + acetoacetyl-CoA

643838

-

2.8.3.9

epsilon-acetyl-CoA + acetoacetate = acetate + acetoacetyl-CoA

643837

-

2.8.3.18

3 entries

2.8.3.5

2 entries

2.8.3.9

3 entries

3.7.1.2

acetoacetate + H2O = acetate

289242

1qco, 3D-view

4.1.1.4

acetoacetate + H+ = acetone + CO2

650919, 653267, 677705, 705516, 746884, 677776, 705885, 726757, 726777, 748436

-

4.1.1.4

acetoacetate + proton = acetone + CO2

650919

-

4.1.1.4

Acetoacetate = ?

4538, 4522

-

4.1.1.4

Acetoacetate = Acetone + CO2

4523, 4522, 4524, 4525, 4526, 4527, 4528, 4529, 4530, 4531, 4532, 4533, 4534, 4535, 4536, 4537, 4538, 4539, 4540, 4541, 715025

-

4.1.1.4

4 entries

6.2.1.16

ATP + acetoacetate + CoA = AMP + diphosphate + acetoacetyl-CoA

653080, 720477, 650, 651, 652, 649794, 650484, 673444, 690593, 728335, 649800, 744249, 653079, 744226, 744906, 746014, 649, 647, 648

-

Product in Enzyme-catalyzed Reactions (75 results)

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Show Product (75 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.276

D-3-hydroxybutyrate + NADP+ = 3-oxobutyrate + NADPH

0

-

1.1.1.276

L-3-hydroxybutyrate + NADP+ = 3-oxobutyrate + NADPH

0

-

1.1.1.30

(R)-2-hydroxybutanoate + NAD+ = acetoacetate + NADH

0

3vdr, 3D-view

1.1.1.30

(R)-2-hydroxybutanoate + NAD+ = acetoacetate + NADH

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + 3-acetylpyridine adenine dinucleotide = acetoacetate + 3-acetylpyridine adenine dinucleotideH2

286528

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + 3-acetylpyridine adenine dinucleotide = acetoacetate + 3-acetylpyridine adenine dinucleotideH2

286528

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH

286540, 286524, 286526, 286512, 286513, 286519, 286516, 286518, 286520, 286521, 286522, 286529, 286533, 286536, 286514, 286517, 286525, 286527, 286528, 286530, 286535, 286538, 286542, 286543, 286523, 286531, 0, 286539, 286541, 286532, 286537, 286515, 286534

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH

286540, 286524, 286526, 286512, 286513, 286519, 286516, 286518, 286520, 286521, 286522, 286529, 286533, 286536, 286514, 286517, 286525, 286527, 286528, 286530, 286535, 286538, 286542, 286543, 286523, 286531, 0, 286539, 286541, 286532, 286537, 286515, 286534

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADH + H+ = acetoacetate + NAD+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADH + H+ = acetoacetate + NAD+

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADP+ = acetoacetate + NADPH

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutanoate + NADP+ = acetoacetate + NADPH

0

6zzo, 3D-view

1.1.1.30

(R)-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

(R)-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.30

4-hydroxybutanoate + NAD+ = acetoacetate + NADH

0

3vdr, 3D-view

1.1.1.30

4-hydroxybutanoate + NAD+ = acetoacetate + NADH

0

6zzo, 3D-view

1.1.1.30

D-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

D-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.30

poly-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

3vdr, 3D-view

1.1.1.30

poly-3-hydroxybutyrate + NAD+ = acetoacetate + NADH + H+

0

6zzo, 3D-view

1.1.1.45

DL-3-hydroxybutanoate + NADH + H+ = acetoacetate + NAD+

0

-

1.1.1.45

L-3-hydroxybutanoate + NADH = acetoacetate + NAD+

0

-

1.1.99.24

(S)-3-hydroxybutanoate + 2-oxoglutarate = acetoacetate + (R)-2-hydroxyglutarate

0

-

1.1.99.24

L-3-hydroxybutyrate + 2-oxoglutarate = acetoacetate + 2-oxoglutarate

286147, 287797

-

1.1.99.24

L-3-hydroxybutyrate + succinic semialdehyde = acetoacetate + 4-hydroxybutyrate

286147, 287797

-

1.8.1.5

2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+ = 2-mercaptoethanesulfonate + acetoacetate + NADP+

288637, 288638, 288639, 0

-

1.8.1.5

2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH = 2-mercaptoethanesulfonate + acetoacetate + NADP+

0

-

1.8.1.5

2-oxopropyl-coenzyme M + CO2 + NADPH = coenzyme M + acetoacetate + NADP+

0

-

1.8.1.5

CO2 + acetoacetate = acetoacetate + CO2

288638

-

1.1.1.276

2 entries

1.1.1.30

20 entries

1.1.1.45

2 entries

1.1.99.24

3 entries

1.8.1.5

4 entries

2.3.1.247

(5S)-5-amino-3-oxohexanoate + acetyl-CoA = L-3-aminobutanoyl-CoA + acetoacetate

0

-

2.6.1.18

L-beta-amino-n-butyric acid + pyruvate = 3-oxo-n-butyric acid + alanine

0

-

2.6.1.18

L-beta-amino-n-butyric acid + pyruvate = 3-oxobutyrate + alanine

0

-

2.6.1.18

2 entries

2.6.1.40

DL-3-amino-n-butanoate + pyruvate = 3-oxobutanoate + L-alanine

0

-

2.6.1.55

DL-3-aminobutyrate + 2-oxoglutarate = 3-oxobutyrate + L-glutamate

636678, 636679

-

2.8.3.8

acetoacetyl-CoA + acetate = acetoacetate + acetyl-CoA

0

-

2.8.3.9

3-hydroxypropanoate + acetoacetyl-CoA = 3-hydroxypropanoyl-CoA + acetoacetate

0

-

2.8.3.9

3-mercaptopropionate + acetoacetyl-CoA = 3-mercaptopropionyl-CoA + acetoacetate

0

-

2.8.3.9

3-methylvinylacetate + acetoacetyl-CoA = 3-methylvinylacetyl-CoA + acetoacetate

0

-

2.8.3.9

4-hydroxybutyrate + acetoacetyl-CoA = 4-hydroxybutanoyl-CoA + acetoacetate

0

-

2.8.3.9

4-pentenoate + acetoacetyl-CoA = 4-pentenoyl-CoA + acetoacetate

0

-

2.8.3.9

acetate + acetoacetyl-CoA = acetyl-CoA + acetoacetate

643839, 643838, 0, 643837

-

2.8.3.9

acrylate + acetoacetyl-CoA = acrylyl-CoA + acetoacetate

0

-

2.8.3.9

butanoate + acetoacetyl-CoA = butanoyl-CoA + acetoacetate

643837, 643839, 643838, 0

-

2.8.3.9

crotonate + acetoacetyl-CoA = crotonyl-CoA + acetoacetate

643838

-

2.8.3.9

DL-2-hydroxybutyrate + acetoacetyl-CoA = 2-hydroxybutyryl-CoA + acetoacetate

0

-

2.8.3.9

DL-2-hydroxypentanoate + acetoacetyl-CoA = 2-hydroxypentanoyl-CoA + acetoacetate

0

-

2.8.3.9

DL-3-hydroxybutyrate + acetoacetyl-CoA = 3-hydroxybutyryl-CoA + acetoacetate

0

-

2.8.3.9

formate + acetoacetyl-CoA = formyl-CoA + acetoacetate

0

-

2.8.3.9

isobutyrate + acetoacetyl-CoA = isobutyryl-CoA + acetoacetate

0

-

2.8.3.9

isopentanoate + acetoacetyl-CoA = isopentanoyl-CoA + acetoacetate

0

-

2.8.3.9

monochloroacetate + acetoacetyl-CoA = monochloroacetyl-CoA + acetoacetate

0

-

2.8.3.9

octanoate + acetoacetyl-CoA = octanoyl-CoA + acetoacetate

0

-

2.8.3.9

pentanoate + acetoacetyl-CoA = pentanoyl-CoA + acetoacetate

643838

-

2.8.3.9

propionate + acetoacetyl-CoA = propionyl-CoA + acetoacetate

643839, 643838

-

2.8.3.9

vinylacetate + acetoacetyl-CoA = vinylacetyl-CoA + acetoacetate

0

-

2.8.3.9

20 entries

3.1.1.8

acetoacetylcholine + H2O = acetoacetate + choline

0

-

3.1.2.1

acetoacetyl-CoA + H2O = CoA + acetoacetate

0

-

3.1.2.1

acetoacetyl-CoA = acetoacetate + CoA

0

-

3.1.2.1

2 entries

3.1.2.11

acetoacetyl-CoA + H2O = acetoacetate + CoA

80975, 80977, 5360, 80971, 80973, 80976, 80980, 80972, 80978, 80979

-

3.1.2.18

acetoacetyl-CoA + H2O = acetoacetate + CoA

0

-

3.1.2.2

acetoacetyl-CoA + H2O = CoA + acetoacetate

0, 646200, 646165

-

3.1.2.20

acetoacetyl-CoA + H2O = CoA + acetoacetate

0, 646165

-

3.1.2.32

acetoacetyl-CoA + H2O = 3-oxobutanoic acid + CoA

0

-

3.1.2.32

S-ethyl-acetothioacetate + H2O = 3-oxobutanoic acid + thioethanol

0

-

3.1.2.32

2 entries

3.1.2.6

S-acetoacetylglutathione + H2O = acetoacetate + glutathione

0

-

3.5.1.97

N-3-oxobutanoyl-L-homoserine lactone + H2O = L-homoserine lactone + 3-oxobutanoic acid

0

-

3.7.1.2

4-fumarylacetoacetate + H2O = acetoacetate + fumarate

289257, 0, 289247, 289240, 289245, 289241, 289242, 289246

1qco, 3D-view

3.7.1.2

maleylacetoacetate + H2O = acetoacetate + maleate

0

1qco, 3D-view

3.7.1.2

triacetic acid + H2O = acetoacetic acid + acetic acid

289239

1qco, 3D-view

4.1.3.4

(S)-3-Hydroxy-3-methylglutaryl-CoA = Acetyl-CoA + acetoacetate

649475, 650252, 652427, 652699, 0, 653126

-

4.1.3.4

3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

0

-

6.4.1.6

acetone + CO2 + ATP + H2O = acetoacetate + AMP + phosphate

349805, 0, 349804, 349806

-

6.4.1.6

acetone + CO2 + GTP + H2O = acetoacetate + GMP + phosphate

349805

-

3.7.1.2

3 entries

4.1.3.4

2 entries

6.4.1.6

2 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.3.5.1

-

723986

-

Inhibitor in Enzyme-catalyzed Reactions (27 results)

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Show Inhibitors (27 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.10

50% inhibition at 0.63 mM

656049

-

1.1.1.10

50% inhibition at 1.8 mM

656049

-

1.1.1.10

50% inhibition at 2.5 mM

656049

-

1.1.1.10

3 entries

1.1.1.19

-

286147

-

1.1.1.21

-

286247

-

1.1.1.30

inhibition above 1 mM, 2 mM, 89% inhibition

286534

3vdr, 3D-view

1.1.1.30

inhibition above 1 mM, 2 mM, 89% inhibition

286534

6zzo, 3D-view

1.1.1.30

substrate inhibition, above 5 mM, noncompetitive vs. NADH

286532

3vdr, 3D-view

1.1.1.30

substrate inhibition, above 5 mM, noncompetitive vs. NADH

286532

6zzo, 3D-view

1.1.1.30

4 entries

1.1.1.45

competitive inhibitor

286910

-

1.1.1.88

-

657303

-

1.1.1.88

competivive inhibitor vs. mevalonate, non inhibitory vs. NAD+

287498

-

1.1.1.88

2 entries

1.14.99.1

weak

438373

-

1.8.1.5

mixed noncompetitive inhibition

765078

-

2.8.3.13

-

643833

-

2.8.3.13

non-competitive inhibition

643832

-

2.8.3.5

-

645978

-

2.8.3.5

5 mM

645974

-

2.8.3.5

kinetics; product inhibition

645967

-

2.8.3.5

product inhibition

672216

-

2.8.3.5

substrate inhibition above 1 mM

645973

-

2.8.3.13

2 entries

2.8.3.5

5 entries

3.5.1.54

Ki 0.3 mM

209196

-

3.7.1.2

1 mM, 30% inhibition

289242

1qco, 3D-view

4.1.3.4

-

650252

-

4.4.1.1

treatment with 0.025-0.035 mM H2O2, 4-8 mM acetoacetate and high D-glucose of 25 mM causes a significant decrease in enzyme protein expression, enzyme activity, and H2S levels, and an increase in intracellular reactive oxygen species production compared with those in normal controls

730038

-

5.3.2.1

-

703331

-

5.3.2.2

-

2874

-

3D Structure of Enzyme-Ligand-Complex (PDB) (21 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (21 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

3vdr, 3D-view

1.1.1.30

6zzo, 3D-view

1.1.1.30

18 entries

1.1.1.35

1e3w, 3D-view

3.7.1.2

1qco, 3D-view

4.1.3.5

1ysl, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (27 results)

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Show Turnover Number (27 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.30

4.5

-

mutant T190A

698660

1.1.1.30

4.9

-

recombinant enzyme with C-terminal His-tag, at pH 6.5 and 30°C

737912

1.1.1.30

5.1

-

mutant T190C

698660

1.1.1.30

30

-

mutant L215A

698660

1.1.1.30

87

-

mutant L215V

698660

1.1.1.30

97.16

-

recombinant enzyme with N-terminal His-tag, at pH 6.5 and 30°C

737912

1.1.1.30

100

-

-

695653

1.1.1.30

100

-

30°C

669544

1.1.1.30

110

-

-

695653

1.1.1.30

110

-

30°C

669544

1.1.1.30

120

-

wild-type

698660

1.1.1.30

125

-

mutant T190S

698660

1.1.1.30

150

-

-

695653

1.1.1.30

13 entries

1.13.11.50

8.5

-

-

657866

1.8.1.5

0.263

-

-

288638

2.8.3.18

36.5

-

-

692865

2.8.3.18

36.5

-

pH 8.0, 25°C

692865

2.8.3.5

9.17

-

pH 8.1, 21-22°C, mutant C28S

672216

2.8.3.5

35

-

pH 8.1, 21-22°C, mutant C196S

672216

2.8.3.5

98.3

-

pH 8.1, 21-22°C, wild-type enzyme

672216

4.1.1.4

30

-

mutant enzyme K116N

4540

4.1.1.4

38

-

mutant enzyme K116C

4540

4.1.1.4

165

-

at 25°C, in 50 mM phosphate buffer, pH 5.95

705885

4.1.1.4

302

-

mutant enzyme K116R

4540

4.1.1.4

349

-

at 25°C, in 50 mM phosphate buffer, pH 5.95

705885

4.1.1.4

1560

-

wild-type enzyme

4540

2.8.3.18

2 entries

2.8.3.5

3 entries

4.1.1.4

6 entries

6.2.1.16

5.89

-

pH 7.5, 30°C, recombinant enzyme

746014

K_M Value (62 results)

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Show KM Value (62 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.30

0.00547

-

-

286515

1.1.1.30

0.146

-

euthermic state, brain

655126

1.1.1.30

0.149

-

liver, soluble enzyme

286536

1.1.1.30

0.15

-

-

286534

1.1.1.30

0.15

-

euthermic state, liver

655126

1.1.1.30

0.17

-

recombinant enzyme with N-terminal His-tag, at pH 6.5 and 30°C

737912

1.1.1.30

0.24

-

reduction reaction, pH 5.0, 55°C

656326

1.1.1.30

0.25

-

-

695653

1.1.1.30

0.26

-

-

286535

1.1.1.30

0.29

-

pH 7.0, 37°C

655261

1.1.1.30

0.312

-

heart, soluble enzyme

286536

1.1.1.30

0.37

-

wild-type

698660

1.1.1.30

0.59

-

-

286525

1.1.1.30

1.1

-

-

695653

1.1.1.30

1.1

-

30°C

669544

1.1.1.30

1.1

-

mutant T190S

698660

1.1.1.30

1.3

-

-

695653

1.1.1.30

1.3

-

30°C

669544

1.1.1.30

1.3

-

mutant L215V

698660

1.1.1.30

7.7

-

mutant T190C

698660

1.1.1.30

8.3

-

mutant L215A

698660

1.1.1.30

8.7

-

cyanylated enzyme

286525

1.1.1.30

10.47

-

recombinant enzyme with C-terminal His-tag, at pH 6.5 and 30°C

737912

1.1.1.30

32

-

mutant T190A

698660

1.1.1.45

6.4

-

cofactor NADH, pH 6.3

286905

1.1.1.45

8.3

-

at pH 8.5, rabbit liver GDH

669147

1.1.1.45

9.9

-

at pH 8.5, recombinant rabbit GDH

669147

1.1.1.30

24 entries

1.1.1.45

3 entries

1.13.11.50

0.0091

-

-

657866

1.8.1.5

6.3

-

-

288638

2.8.3.18

130

-

-

692865

2.8.3.18

130

-

pH 8.0, 25°C

692865

2.8.3.5

0.0002

-

pH 8.1, 25°C, presence of sodium sulfate

645995

2.8.3.5

0.05

-

C28S mutant

672216

2.8.3.5

0.05

-

pH 8.1, 21-22°C, mutant C28S

672216

2.8.3.5

0.07

-

cosusbstrate: succinyl-CoA

645973

2.8.3.5

0.1

-

C28A mutant

672216

2.8.3.5

0.1

-

pH 8.1, 21-22°C, mutant C196S

672216

2.8.3.5

0.1

-

pH 8.1, 21-22°C, wild-type enzyme

672216

2.8.3.5

0.1

-

wild-type SCOT

672216

2.8.3.5

0.2

-

cosusbstrate: succinyl-CoA, pH 8.1

645967

2.8.3.5

0.2

-

heart, succinyl CoA as second substrate

645972

2.8.3.5

0.21

-

kidney, skeletal muscle, pH 8.1, 25°C

645972

2.8.3.5

0.31

-

brain, pH 8.1, 25°C

645972

2.8.3.5

0.44

-

pH 8.1, 25°C

645978

2.8.3.9

1.1

-

pH 7.5, 25°C, butyryl-CoA level of 0.18 mM

643838

2.8.3.9

1.4

-

pH 7.5, 25°C, butyryl-CoA level of 0.23 mM

643838

2.8.3.9

1.8

-

pH 7.5, 25°C, butyryl-CoA level of 0.37 mM

643838

4.1.1.4

0.94

-

-

4523

4.1.1.4

4.1

-

at 25°C, in 50 mM phosphate buffer, pH 5.95

705885

4.1.1.4

5.2

-

-

4535

4.1.1.4

5.7

-

at 25°C, in 50 mM phosphate buffer, pH 5.95

705885

4.1.1.4

7

-

-

4536

4.1.1.4

8

-

-

4527

4.1.1.4

8.2

-

wild-type enzyme

4540

4.1.1.4

8.4

-

mutant enzyme K116C

4540

4.1.1.4

10

-

mutant enzyme K116N

4540

4.1.1.4

14.7

-

mutant enzyme K116R

4540

4.1.1.4

400

-

polymyxin MI

4523

6.2.1.16

0.008

-

-

647

6.2.1.16

0.07

-

-

650

6.2.1.16

0.076

-

-

649

6.2.1.16

0.3

-

pH 8.4

653080

2.8.3.18

2 entries

2.8.3.5

13 entries

2.8.3.9

3 entries

4.1.1.4

11 entries

6.2.1.16

4 entries

K_i Value (6 results)

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Show KI Value (6 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.88

3

-

standard conditions, inhibition by substrate analog

657303

2.8.3.13

0.5

-

pH 8.5, 30°C

643832

2.8.3.5

0.78

-

pH 8.1

645967

2.8.3.5

3.7

-

pH 8.1, 25°C

645978

2.8.3.5

2 entries

3.5.1.54

0.3

-

-

209196

4.1.3.4

0.021

-

-

650252

References & Links

Literature References (194)

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Show Reference (194 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

647

6539623

Purification and characterization of acetoacetyl-CoA synthetase from rat liver

1984

Ito, M.; Fukui, T.; Kamokari, M.; Saito, T.; Tomita, K.

Biochim. Biophys. Acta

794

183-193

648

2862567

Rat liver acetoacetyl-CoA synthetase

1985

Bergstrom, J.D.; Edmond, J.

Methods Enzymol.

110

3-9

649

7140777

Purification and characterization of acetoacetyl-CoA synthetase from Zoogloea ramigera 1-16-M

1982

Fukui, T.; Ito, M.; Tomita, K.

Eur. J. Biochem.

127

423-428

650

4073493

A radiochemical assay for acetoacetyl-CoA synthetase

1985

Bergstrom, J.D.; Edmond, J.

Anal. Biochem.

149

358-364

651

5125223

A role of acetoacetyl-CoA synthetase in acetoacetate Utilization by rat liver cell fractions

1971

Stern, J.R.

Biochem. Biophys. Res. Commun.

44

1001-1007

652

6501306

The regulation of acetoacetyl-CoA synthetase activity by modulators of cholesterol synthesis in vivo and the utilization of acetoacetate for cholesterogenesis

1984

Bergstrom, J.D.; Wong, G.A.; Edwards, P.A.; Edmond, J.

J. Biol. Chem.

259

14548-14553

2874

5781999

Oxalacetate keto-enol tautomerase. Purification and characterization

1969

Annett, R.G.; Kosicki, G.W.

J. Biol. Chem.

244

2059-2067

3378

6811551

Pathway of lysine degradation in Fusobacterium nucleatum

1982

Barker, H.A.; Kahn, J.M.; Hedrick, L.

J. Bacteriol.

152

201-207

4522

16347575

Expression of solvent-forming enzymes and onset of solvent production in batch cultures of Clostridium beijerinckii

1988

Yan, R.T.; Zhu, C.X.; Golemboski, C.; Chen, J.S.

Appl. Environ. Microbiol.

54

642-648

4523

-

Acetoacetate decarboxylase and a peptide with similar activity produced by Bacillus polymyxa

1986

Kimura, Y.; Yasuda, N.; Tanigaki-Nagae, H.; Nakabayashi, T.; Matsunga, H.M; Kimura, M.; Matsuoka, A.

Agric. Biol. Chem.

50

2509-2516

4524

-

Stereochemical imperative in enzymic decarboxylation. Stereochemical course of the decarboxylation catalyzed by acetoacetate decarboxylase

1984

Rozzel, J.D.; Benner, S.A.

J. Am. Chem. Soc.

106

4937-4941

4525

-

Stereospecificity and stereochemical infidelity of acetoacetate decarboxylase (AAD)

1981

Benner, S.A.; Rozzel, J.D.

J. Am. Chem. Soc.

103

993-994

4526

4360355

Inhibition of acetoacetate decarboxylase by ketophosphonates. Structural and dynamic probes of the active site

1974

Kluger, R.; Nakaoka, K.

Biochemistry

13

910-914

4527

-

Acetoacetate decarboxylase

1972

Fridovich, I.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

6

255-270

4528

5469164

The thermal inactivation of acetoacetate decarboxylase

1970

Autor, A.P.; Fridovich, I.

J. Biol. Chem.

245

5223-5227

4529

5469163

The interactions of acetoacetate decarboxylase with carbonyl compounds, hydrogen cyanide, and an organic mercurial

1970

Autor, A.P.; Fridovich, I.

J. Biol. Chem.

245

5214-5222

4530

-

Acetoacetate decarboxylase from Clostridium acetobutylicum

1969

Westheimer, F.H.

Methods Enzymol.

14

231-241

4531

5657855

Acetoacetate decarboxylase. Reaction with acetopyruvate

1968

Tagaki, W.; Guthrie, J.P.; Westheimer, F.H.

Biochemistry

7

905-913

4532

5657854

Acetoacetate decarboxylase. Catalysis of hydrogen-deuterium exchange in acetone

1968

Tagaki, W.; Westheimer, F.H.

Biochemistry

7

901-905

4533

5657853

Acetoacetate decarboxylase. The molecular weight of the enzyme and subunits

1968

Tagaki, W.; Westheimer, F.H.

Biochemistry

7

895-900

4534

5657852

Acetoacetate decarboxylase. Reassociation of subunits

1968

Tagaki, W.; Westheimer, F.H.

Biochemistry

7

891-894

4535

5640970

A study of the interaction of acetoacetic decarboxylase with several inhibitors

1968

Fridovich, I.

J. Biol. Chem.

243

1043-1051

4536

6027255

Acetoacetic decarboxylase. Activation by heat

1967

Neece, M.S.; Fridovich, I.

J. Biol. Chem.

242

2939-2944

4537

5657856

Acetoacetate decarboxylase. Selective acetylation of the enzyme

1968

O'Leary, M.H.; Westheimer, F.H.

Biochemistry

7

913-919

4538

-

Induction of acetoacetate decarboxylase in Clostridium acetobutylicum

1985

Ballongue, J.; Amine, J.; Masion, E.; Petitdemange, H.; Gay, R.

FEMS Microbiol. Lett.

29

273-277

4539

2254264

Cloning, sequencing, and molecular analysis of the acetoacetate decarboxylase gene region from Clostridium acetobutylicum

1990

Gerischer, U.; Durre, P.

J. Bacteriol.

172

6907-6918

4540

8555196

Mechanism of the reaction catalyzed by acetoacetate decarboxylase. Importance of lysine 116 in determining the pKa of the active-site lysine 115

1996

Highbarger, L.A.; Gerlt, J.A.; Kenyon, G.L.

Biochemistry

35

41-46

4541

2268159

Purification of acetoacetate decarboxylase from Clostridium acetobutylicum ATCC 824 and cloning of the acetoacetate decarboxylase gene in Escherichia coli

1990

Petersen, D.J.; Bennett, G.N.

Appl. Environ. Microbiol.

56

3491-3498

5360

6131897

A survey of enzymes which generate or use acetoacetyl thioesters in rat liver

1983

Aragon, J.J.; Lowenstein, J.M.

J. Biol. Chem.

258

4725-4733

80971

5690557

Acetoacetyl coenzyme A deacylase activity in liver mitochondria from fed and fasted rats

1968

Burch, R.E.; Triantafillou, D.

Biochemistry

7

1009-1013

80972

13818236

Enzymes of ketone body metabolism. II. Properties of an acetoacetate-synthesizing enzyme prepared from ox liver

1960

Drummond, G.I.; Stern, J.R.

J. Biol. Chem.

235

318-325

80973

640138

Rat brain acetoacetyl-coenzyme A deacylase [proceedings

1978

Patel, T.B.; Clark, J.B.

Biochem. Soc. Trans.

6

126-128

80975

38142

The role of 3-oxo acid-CoA transferase in the regulation of ketogenesis in the liver

1979

Zammit, V.A.; Beis, A.; Newsholme, E.A.

FEBS Lett.

103

212-215

80976

34385

Acetoacetate metabolism in rat brain. Development of acetoacetyl-coenzyme A deacylase and 3-hydroxy-3-methylglutaryl-coenzyme A synthase

1978

Patel, T.B.; Clark, J.B.

Biochem. J.

176

951-958

80977

4072

On the occurrence of enzymes of ketone-body metabolism in human adipose tissue

1976

Rous, S.

Biochem. Biophys. Res. Commun.

69

74-78

80978

5449124

Enzymes involved in acetoacetate formation in various bovine tissues

1970

Baird, G.D.; Hibbitt, K.G.; Lee, J.

Biochem. J.

117

703-709

80979

-

Acetoacetate formation in bovine tissues

1969

Baird, G.D.; Hibbitt, K.G.

Biochem. J.

115

49

80980

5667251

Activity and intracellular distribution of enzymes of ketone-body metabolism in rat liver

1968

Williamson, D.H.; Bates, M.W.; Krebs, H.A.

Biochem. J.

108

353-361

209196

-

Purification and properties of the allophanate hydrolase from Chlamydomonas reinhardii

1982

Maitz, G.S.; Haas, E.M.; Castric, P.A.

Biochim. Biophys. Acta

714

486-491

286147

1784339

An overview of gamma-hydroxybutyrate catabolism: the role of the cytosolic NADP+-dependent oxidoreductase EC 1.1.1.19 and of a mitochondrial hydroxyacid-oxoacid transhydrogenase in the initial, rate-limiting step in this pathway

1991

Kaufman, E.E.; Nelson, T.

Neurochem. Res.

16

965-974

286247

14275148

Isolation and properties of lens aldose reductase

1965

Hayman, S.; Kinoshita, J.H.

J. Biol. Chem.

240

877-882

286512

-

(R)-3-Hydroxybutyrate dehydrogenase: selective phosphatidylcholine binding by the C-terminal domain

2000

Loeb-Hennard, C.; McIntyre, J.O.

Biochemistry

39

11929-11938

286513

8679568

Wild type and mutant human heart (R)-3-hydroxybutyrate dehydrogenase expressed in insect cells

1996

Green, D.; Marks, a.R.; Fleischer, S.; McIntyre, J.O.

Biochemistry

35

8158-8165

286514

8608144

Specific interaction of(R)-3-hydroxybutyrate dehydrogenase with membrane phosphatidylcholine as studied by ESR spectroscopy in oriented phospholipid multilayers: coenzyme binding enhances the interaction with phosphatidylcholine

1996

Klein, K.; Rudy, B.; McIntyre, J.O.; Fleischer, S.; Trommer, W.E.

Biochemistry

35

3044-3049

286515

7526614

Occurence, purification and properties of the staphylococcal beta-hydroxybutyrate dehydrogenase

1994

Szewczyk, E.; Rozolska, M.

Acta Microbiol. Pol.

43

33-45

286516

7686368

Monoclonal antibodies for structure-function studies of (R)-3-hydroxybutyrate dehydrogenase, a lipid-dependent membrane-bound enzyme

1993

Adam, Pascal; Duncan, T.M.; McIntyre, J.O.; Carter, C.E.; Fu, C.; Melin, M.; Latruffe, N.; Fleischer, S.

Biochem. J.

292

863-872

286517

8280053

Effect of selective thiol-group derivatization on enzyme kinetics of (R)3-hydroxybutyrate dehydrogenase

1993

Dalton, L.A.; McIntyre, J.O.; Fleischer, S.

Biochem. J.

296

563-569

286518

8487494

Inhibition of succinate dehydrogenase and beta-hydroxybutyrate dehydrogenase activities by methylmalonate in brain and liver of developing rats

1993

Dutra, J.C.; Dutra-Filho, C.S.; Cardozo, S.E.C.; Wannmacher, C.M.D.; Sarkis, J.J.F.; Wajner, M.

J. Inherit. Metab. Dis.

16

147-153

286519

1639787

Molecular cloning and characterization of (R)3-hydroxybutyrate dehydrogenase from human heart

1992

Marks, A.R.; McIntyre, J.O.; Duncan, T.M.; Erdjument-Bromage, H.; Tempst, P.; Fleischer, S.

J. Biol. Chem.

267

15459-15463

286520

1804504

Post-transcriptional analysis of rat mitochondrial D-3-hydroxybutyrate dehydrogenase control through development and physiological stages

1991

Bailly, A.; Lone, Y.C.; Latruffe, N.

Biol. Cell.

73

121-129

286521

3355176

Comparison of 3-hydroxybutyrate dehydrogenase from bovine heart and rat liver mitochondria

1988

McIntyre, J.O.; Latruffe, N.; Brenner, S.C.; Fleischer, S.

Arch. Biochem. Biophys.

262

85-98

286522

3676253

Noncooperative vs. cooperative reactivation of D-beta-hydroxybutyrate dehydrogenase: multiple equilibria for lecithin binding are determined by the physical state (soluble vs. bilayer) and composition of the phospholipids

1987

Cortese, J.D.; Fleischer, S.

Biochemistry

26

5283-5293

286523

3494445

3-Hydroxyisobutyrate dehydrogenase, an impurity in commercial 3-hydroxybutyrate dehydrogenase

1987

Worral, E.B.; Gassain, S.; Cox, D.J.; Sugden, M.C.; Palmer, T.N.

Biochem. J.

241

297-300

286524

-

Kinetics of D-3-hydroxybutyrate dehydrogenase from Paracoccus denitrificans

1986

Kovar, J.; Matyskova, I.; Matyska, L.

Biochim. Biophys. Acta

871

302-309

286525

3013239

Cyanylation of 3-hydroxybutyrate dehydrogenase

1986

Dubois, H.; Fritsche, T.M.; Trommer, W.E.; McIntyre, J.O.; Fleischer, S.

Biol. Chem. Hoppe-Seyler

367

343-353

286526

-

Purification and properties of D-3-hydroxybutyrate dehydrogenase from Paracoccus denitrificans

1985

Matyskova I.; Kovar, J.; Racek, P.

Biochim. Biophys. Acta

839

300-307

286527

3986202

A rapid and efficient procedure for the purification of mitochondrial beta-hydroxybutyrate dehydrogenase

1985

Burnett, B.K.; Khorana, H.G.

Biochim. Biophys. Acta

815

51-56

286528

7213590

Inhibition of D(-)-beta-hydroxybutyrate dehydrogenase by butanedione, phenylglyoxal, and diethyl pyrocarbonate

1981

Phelps, D.C.; Hatefi, Y.

Biochemistry

20

459-463

286529

-

D-3-Hydroxybutyrate dehydrogenase and metabolism of ketone bodies by rat stomach

1984

MacGill, A.K.; Anderson, N.G.; Trotman, C.N.A.; Carrington, J.M.; Hanson, P.J.

Biochem. Soc. Trans.

607

788

286530

6822516

Target size of D-beta-hydroxybutyrate dehydrogenase

1983

McIntyre, J.O.; Churchill, P.; Maurer, A.; Berenski, C.J.; Jung, C.Y.; Fleischer, S.

J. Biol. Chem.

258

953-959

286531

6981412

The rapid purification of 3-hydroxybutyrate dehydrogenase and malate dehydrogenase on triazine dye affinity matrices

1982

Scawen, M.D.; Darbyshire, J.; Harvey, M.J.; Atkinson, T.

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