Ligand oxaloacetic acid

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Basic Ligand Information

Molecular Structure

C₄H₄O₅

oxaloacetic acid

KHPXUQMNIQBQEV-UHFFFAOYSA-N

Synonyms:

2-oxo-succinate, 2-oxobutan-1,4-dioate, 2-oxobutanedioate, 2-oxobutanedioic acid, 2-oxosuccinate, 2-oxosuccinic acid, 3-oxosuccinate, alpha-keto-succinate, keto-oxaloacetate, oxalacetate, oxalacetic acid, oxaloacetate

BRENDA

alanine metabolism, anapleurotic synthesis of oxalacetate, C4 and CAM-carbon fixation, citric acid cycle, gluconeogenesis

more

KEGG

2-Oxocarboxylic acid metabolism, Alanine, aspartate and glutamate metabolism, Benzoate degradation, Biosynthesis of alkaloids derived from histidine and purine, Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid

more

MetaCyc

2-methylcitrate cycle I, 2-methylcitrate cycle II, 3-methylarginine biosynthesis, acetyl-CoA biosynthesis III (from citrate), anaerobic energy metabolism (invertebrates, cytosol)

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Show all BRENDA pathways known for oxaloacetic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (87 results)

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1.1.1.290

oxaloacetic acid + NAD+ = ?

oxaloacetate + NADH + H+ = malate + NAD+

737315

1.1.99.7

(S)-lactate + oxaloacetate = malate + pyruvate

287844, 287850, 287845

1.4.1.21

2 entries

2.1.3.1

propionyl-CoA + oxaloacetate = (S)-methylmalonyl-CoA + pyruvate

acetyl-CoA + H2O + oxaloacetic acid = ? + CoA

740585

2.3.3.2

lauroyl-CoA + H2O + oxaloacetate = (2S,3S)-2-hydroxytridecane-1,2,3-tricarboxylate + CoA

ADP + phosphate + acetyl-CoA + oxaloacetate = ATP + citrate + CoA

735902, 736752, 736797, 735597, 735620, 736093, 736591, 736996, 735713, 736127

2.6.1.31

pyridoxamine + oxaloacetate = pyridoxal + L-aspartate

639961, 639962

3.7.1.1

oxaloacetate + H2O = oxalate + acetate

210609, 210612, 719546, 210614, 210610, 670169, 687682, 686268, 734415, 719879, 734735, 735295, 210608

4.1.1.112

3 entries

4.1.1.31

phosphate + oxaloacetate = phosphoenolpyruvate + HCO3-

727236, 727209, 728484, 727178, 727533, 728519

In Vivo Product in Enzyme-catalyzed Reactions (67 results)

(S)-malate + NAD+ = oxaloacetate + NADH + H+

1.1.1.82

(S)-malate + NADP+ = oxaloacetate + NADPH + H+

D-aspartic acid + H2O + O2 = oxaloacetate + NH3 + H2O2

1.4.3.16

2 entries

1.4.3.2

L-Asp + H2O + O2 = oxaloacetate + NH3 + H2O2

1.4.3.3

2 entries

1.4.3.7

D-aspartate + H2O + O2 = oxaloacetate + NH3 + H2O2

395288, 395287, 395286

2.1.3.1

(S)-methylmalonyl-CoA + pyruvate = propanoyl-CoA + oxaloacetate

L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate

639822, 639824, 639840, 639856, 639865, 639875, 639859, 639872, 639871, 639873, 636643, 639815, 639823, 639841, 639842, 639843, 639844, 639855, 639870, 639879, 639884, 639869, 639829, 639868, 639880, 639886, 639816, 639817, 639821, 639831, 639839, 639850, 639864, 639830, 639834, 639828, 639845, 639860, 639836, 639851, 639832, 286649, 639876, 639862, 639814, 639838, 639885, 639849, 639833, 639854, 639846, 639818, 639819, 639837, 639820, 639861, 636718, 639863, 636732, 636660, 639835, 639867, 636719, 639874, 639883, 639878, 639881, 639858, 636716, 639826, 639825, 639882, 639866, 639848

3pdb, 3D-view

2.6.1.35

glyoxylate + L-aspartate = glycine + oxaloacetate

639968, 639967, 639966

2.6.1.70

L-aspartate + 3-phenylpyruvate = oxaloacetate + L-phenylalanine

640191

2.6.1.78

prephenate + L-aspartate = L-arogenate + oxaloacetate

phosphate + phosphoenolpyruvate + CO2 = diphosphate + oxaloacetate

citrate = acetate + oxaloacetate

441599, 492186, 653146, 649579

4.1.3.B3

4-carboxy-4-hydroxy-2-oxoadipate = oxaloacetate + pyruvate

4.2.1.32

L-tartrate = oxaloacetate + H2O

4.2.1.81

(S,S)-tartrate = oxaloacetate + H2O

648403, 648404

4.3.1.16

L-threo-3-hydroxyaspartate = oxaloacetate + NH3

6.4.1.1

3 entries

Substrate in Enzyme-catalyzed Reactions (303 results)

oxalacetic acid + NADPH = ? + NADP+

oxaloacetic acid + NAD+ = ?

oxaloacetate + NADPH = malate + NADP+

287328, 287321

1.1.1.81

oxaloacetate + NAD(P)H = malate + NAD(P)+

oxaloacetate + NADH + H+ = malate + NAD+

737315

1.1.1.96

oxaloacetate + NADH = malate + NAD+

287553

1.1.99.40

D-2-hydroxyglutarate + oxaloacetate = 2-oxoglutarate + malate

740757

1.1.99.7

(S)-lactate + oxaloacetate = malate + pyruvate

287848, 287849, 287844, 287846, 287847, 287850, 287845

1.2.1.51

oxaloacetate + CoA + NADP+ = ? + CO2 + NADPH

oxaloacetate + H2O + methyl viologen = ?

715568

1.4.1.1

oxaloacetate + NH3 + NADH = L-Asp + H2O + NAD+

349566, 349556, 349571, 349573, 349574, 349581, 349547, 349537

1.4.1.16

2-oxosuccinic acid + NH3 + NADPH + H+ = ?

741705

1.4.1.17

methylamine + oxaloacetate + NADPH = aspartic acid + H2O + NADP+

391526

1.4.1.2

oxaloacetate + NADPH + NH3 = L-aspartate + NADP+ + H2O

L-Arg + oxaloacetate + NADH = ?

13301, 13318, 13302, 13323, 13317

1.5.1.17

L-Ala + oxaloacetate + NADH = ?

13374, 13373, 13369

1.5.1.22

3 entries

1.5.1.23

taurine + oxaloacetate + NADH = ?

13440, 13439, 13437

1.5.1.24

L-ornithine + oxaloacetic acid + NADPH + H+ = ? + NADP+ + H2O

712294

1.5.1.28

L-Met + oxaloacetate + NADH = ?

94167

1.5.1.52

(2S)-2-amino-4-[[(1R)-1-carboxy-2-(1H-imidazol-4-yl)ethyl]amino]butanoate + oxaloacetate + NADPH + H+ = ? + NADP+ + H2O

acetyl-CoA + H2O + oxaloacetic acid = ? + CoA

740585

2.3.3.19

acetyl-CoA + H2O + oxalacetic acid = ? + CoA

ADP + phosphate + acetyl-CoA + oxaloacetate = ATP + citrate + CoA

735902, 736752, 736797, 735597, 735620, 736093, 33352, 736591, 736996, 735713, 488211, 736127

2.6.1.1

4 entries

2.6.1.12

L-alanine + oxaloacetate = pyruvate + L-aspartate

636593

2.6.1.13

ornithine + oxaloacetate = DELTA1-pyrroline-5-carboxylate + L-aspartate

637103, 637110, 637107, 637111, 637130

2.6.1.18

beta-alanine + oxaloacetic acid = malonic semialdehyde + L-aspartate

636596

2.6.1.23

4-hydroxy-L-glutamate + oxaloacetate = 4-hydroxy-2-oxoglutarate + L-aspartate

639934, 639935

2.6.1.24

3,5-diiodo-L-tyrosine + oxaloacetate = 3,5-diiodo-4-hydroxyphenylpyruvate + L-aspartate

639936

2.6.1.26

L-3,5,3'-triiodothyronine + oxaloacetate = 3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-2-oxopropanoate + glycine

pyridoxamine + oxaloacetate = pyridoxal + L-aspartate

639961, 639962

2.6.1.36

L-lysine + oxaloacetate = 2-aminoadipate 6-semialdehyde + L-aspartate

637024, 637018, 637023, 637031

2.6.1.39

oxaloacetate + L-glutamate = 2-aminosuccinate + 2-oxoglutarate

659885

2.6.1.40

(R)-3-amino-2-methylpropanoate + oxaloacetate = 2-methyl-3-oxopropanoate + L-aspartate

644426, 644430, 636964

2.6.1.41

D-methionine + oxaloacetate = 4-methylthio-2-oxobutanoate + L-aspartate

3-(3,4-dihydroxyphenyl)-L-alanine + oxaloacetic acid = 3-(3,4-dihydroxyphenyl)pyruvate + L-aspartate

L-serine + oxaloacetate = 3-hydroxypyruvate + L-aspartate

L-leucine + oxaloacetate = 4-methyl-2-oxopentanoate + L-aspartate

639996

2.6.1.64

L-glutamine + oxaloacetate = 2-oxoglutaramate + L-aspartate

639901, 640171, 640172

L-methionine + oxaloacetate = 4-methylsulfanyl-2-oxobutanoate + L-aspartate

636989, 636990

2.6.1.76

L-lysine + oxaloacetic acid = ?

288731

2.6.1.77

taurine + oxaloacetate = ?

640197

2.6.1.78

L-arogenate + oxaloacetate = prephenate + L-aspartate

L-histidinol phosphate + oxaloacetate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-aspartate

637151

2.6.1.B3

(2S,3S,5R,10S,12R,14R,15S,16S)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol + oxaloacetate = (3S,5R,10S,12R,14R,15S,16S)-3,5,10,14,15-pentahydroxy-12,16-dimethylicosan-2-one + L-aspartate

724058

2.8.3.1

acetyl-CoA + oxaloacetate = acetate + oxaloacetyl-CoA

33928

2.8.3.18

succinyl-CoA + oxaloacetate = oxaloacetyl-CoA + succinate

721675

3.7.1.1

oxaloacetate + H2O = oxalate + acetate

210609, 210612, 719546, 210614, 210610, 689936, 670169, 670718, 668652, 687682, 686268, 734415, 719879, 734735, 735295, 210608, 693684

3.7.1.2

oxaloacetate + H2O = ?

oxaloacetate = ?

oxaloacetate + NAD+ = ?

648380

4.1.3.1

oxalacetate = oxalate + acetate

664083

4.1.3.13

Oxaloacetate + glyoxylate = 3-Oxalomalate

5222

4.1.3.16

Oxaloacetate = CO2 + pyruvate

5252, 5243, 5255, 5241

Oxaloacetate = CO2 + pyruvate

acetate + oxaloacetate = citrate

33352, 33363

5.3.2.2

keto-Oxaloacetate = Enol-oxaloacetate

2875, 2874, 2878, 2880, 2877, 2879, 2876

6.2.1.9

ATP + oxaloacetate + CoA = ADP + phosphate + oxaloacetyl-CoA

743968

7.2.4.2

3 entries

Product in Enzyme-catalyzed Reactions (199 results)

malate + NAD+ = 3-oxosuccinate + NADH + H+

1.1.5.4

17 entries

1.1.99.14

DL-malate + acceptor = 2-oxosuccinate + reduced acceptor

1.1.99.6

D-malate + acceptor = oxaloacetate + reduced acceptor

287840

1.13.12.4

(S)-malate + O2 = oxaloacetate + H2O2

440413

1.4.1.1

L-Asp + H2O + NAD+ = oxaloacetate + NH3 + NADH

D-aspartic acid + H2O + O2 = oxaloacetate + NH3 + H2O2

D-Asp + H2O + oxidized 2,6-dichlorophenolindophenol = 2-oxobutanedioate + NH3 + reduced 2,6-dichlorophenolindophenol

1.5.99.13

D-aspartate + oxidized 2,6-dichloroindophenol + H2O = oxaloacetate + NH3 + reduced 2,6-dichloroindophenol

2.1.3.1

(S)-methylmalonyl-CoA + pyruvate = propanoyl-CoA + oxaloacetate

pyruvate + L-aspartate = L-alanine + oxaloacetate

636593

2.6.1.18

beta-alanine + pyruvate = oxaloacetate + alanine

2.6.1.2

L-aspartate + 2-oxoglutarate = 2-oxobutan-1,4-dioate + L-glutamate

glyoxylate + L-aspartate = glycine + oxaloacetate

639968, 639967, 639966

2.6.1.42

3 entries

2.6.1.43

L-aspartate + 4,5-dioxopentanoate = 5-aminolevulinate + oxaloacetate

2.6.1.44

L-aspartate + glyoxylate = 2-oxosuccinate + glycine

640068

2.6.1.49

3-(3,4-dihydroxyphenyl)pyruvate + L-aspartate = 3,4-dihydroxy-L-phenylalanine + oxaloacetate

L-aspartate + pyruvate = oxaloacetate + L-alanine

2.6.1.67

L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate

D-aspartate + 2-oxoadipate = oxaloacetate + 2-aminoadipate

2.6.1.75

L-aspartic acid + 2-oxoglutarate = oxaloacetate + L-glutamate

oxaloacetate 4-methyl ester = oxaloacetate + methanol

Pyruvate + CO2 = Oxaloacetate

phosphate + phosphoenolpyruvate + CO2 = diphosphate + oxaloacetate

33092, 33095, 33098, 33091, 33094, 33093

citrate = acetate + oxaloacetate

33363, 33352, 33349, 33364, 441599, 693, 33358, 33362, 33354, 33360, 698, 33368, 33357, 33346, 33350, 33351, 33353, 33356, 33361, 33367, 33369, 33370, 33372, 492186, 653146, 649579

(2S,3S)-tartrate = oxaloacetate + H2O

4.2.1.81

(S,S)-tartrate = oxaloacetate + H2O

648403, 648404

4.2.1.B26

butynedioyl-CoA = oxaloacetate + CoA

4.3.1.16

3 entries

4.3.1.17

L-threo-3-hydroxyaspartate = oxaloacetate + NH3

4.3.1.20

Erythro-DL-beta-hydroxyaspartate = Oxaloacetate + NH3

L-aspartate + pyridoxal 5'-phosphate = 2-oxo-succinate + pyridoxamine 5'-phosphate

649945

6.3.1.5

ATP + deamido-NAD+ + Asp = AMP + diphosphate + NAD+ + oxaloacetate

6.4.1.1

4 entries

7.2.4.2

Pyruvate + CO2 = Oxaloacetate

4260, 4279

Activator in Enzyme-catalyzed Reactions (10 results)

;

stimulates by chelating and stabilizing Mn3+

439830

1.4.7.1

up to 50% increase in activity

activation

50 mM, increasing enzyme activity by 30%

0.030 mM

Inhibitor in Enzyme-catalyzed Reactions (332 results)

inhibition at 5 mM

above 0.3 mM

10 mM, 38.5% inhibition

286830, 286840, 286885, 286904

1.1.1.81

2.5 mM, 10% inhibition of NADH linked hydroxypyruvate reduction, 20% of NADPH linked reduction

competitive

competitive

competitive to acceptor

10 mM, 50% inhibition, noncompetitive

395375

1.13.12.2

67% inhibition at 5 mM

2-oxoglutarate dehydrogenase complex

weak inhibition, competitive with 2-oxoglutarate

at 6.67 mM 90% inhibition

391727

1.4.3.16

weak inhibition; weak inhibition

slight substrate inhibition

1 mM, 68% inhibition

competitive to 2-oxoglutarate

488164

2.3.3.8

488189, 488205, 658601

in complex with Mg2+, inhibition at low substrate concentrations, inhibition of the translocase component of the glucose 6-phosphatase system

134955

3.2.1.62

50% inhibition of the tartaric acid-stimualted phlorizin hydrolase at 20 mM

a competitive inhibitor

strong inhibition, 8 mM: 59% of activity compared to H2O

1 mM, 90% inhibition

competitive inhibition, 0.2-1 mM

about 68% residual activity at 25 mM

747628

4.1.1.31

4285, 4301, 4305, 4307, 4325, 4332

at 7 mM

competitive, Ki: 0.22 mM

competitive

irreversible

Ki: 8.22 mM

non-competitive inhibition, pyruvate as varied substrate

34848, 34850, 34854

2 mM, 56% residual activity

661410

5.3.1.9

10 mM, 25% inhibition

20 mM, 40% inhibition

3D Structure of Enzyme-Ligand-Complex (PDB) (54 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (162 results)

1.1

in 50 mM Tris-HCl (pH 8.0) with 50 mM NaCl, 1 mM dithiothreitol, at 22°C

724295

Ligand oxaloacetic acid

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (87 results)

In Vivo Product in Enzyme-catalyzed Reactions (67 results)

Substrate in Enzyme-catalyzed Reactions (303 results)

Product in Enzyme-catalyzed Reactions (199 results)

Activator in Enzyme-catalyzed Reactions (10 results)

Inhibitor in Enzyme-catalyzed Reactions (332 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (54 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (162 results)

k_cat Value (Turnover Number) (162 results)