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• • In Vivo Substrate
  • In Vivo Product
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  • Product
  • Cofactor
  • Activator
  • Inhibitor
  • Metals and Ions
  • 3D Structure (PDB)
• Enzyme Kinetic Parameters
• • k_cat Value (Turnover Number)
  • K_M Value
  • K_i Value
  • IC₅₀ Value
• References & Links
• • References
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Ligand adenylosuccinate

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for adenylosuccinate

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Natural Substrate (9 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

2ptr, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

2vd6, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595

5nx9, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

2ptr, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

2vd6, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 1538, 34461, 34449, 34459, 34454, 749293

5nx9, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

2ptr, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

2vd6, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 709392, 710076, 729296, 730526, 729717, 707497, 708663, 729218, 690934, 706979, 694197, 691116

5nx9, 3D-view

4.3.2.2

9 entries

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.4

GTP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

-

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + adenylosuccinate

651921, 649423, 650258, 652965, 651925, 652500, 652193, 649897, 652347, 651884, 652812, 649264, 649265, 652608, 652317, 652356, 649670, 653751, 652929,

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP

652608

1mez, 3D-view

6.3.4.4

3 entries

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

2ptr, 3D-view

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

2vd6, 3D-view

4.3.2.2

adenylosuccinate = adenosine monophosphate + fumarate

734059

5nx9, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

2ptr, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

2vd6, 3D-view

4.3.2.2

adenylosuccinate = AMP + fumarate

664041, 664255, 665595, 681945, 682733, 682738, 682657, 681441

5nx9, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

2ptr, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

2vd6, 3D-view

4.3.2.2

N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP

681945, 682733, 682738, 682657, 681441, 747484, 34465, 34449, 34450, 34456, 1538, 34458, 34454, 1541, 34451, 34461, 34459, 749293

5nx9, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

2ptr, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

2vd6, 3D-view

4.3.2.2

succinyladenosine monophosphate = AMP + fumarate

695003, 693982, 694197, 709392, 710076, 729296, 730526, 729717, 691116, 707497, 708663, 729218, 690934, 706979

5nx9, 3D-view

4.3.2.2

12 entries

Product in Enzyme-catalyzed Reactions (13 results)

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Show Product (13 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

2ptr, 3D-view

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

2vd6, 3D-view

4.3.2.2

fumarate + AMP = N6-(1,2-dicarboxyethyl)AMP

34458, 1541, 34451

5nx9, 3D-view

6.3.4.4

2'-dGTP + IMP + L-aspartate = 2'-dGDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

ATP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

-

1mez, 3D-view

6.3.4.4

ddGTP + IMP + L-aspartate = ddGDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

GTP + IMP + L-Asp = GDP + phosphate + adenylosuccinate

1537, , 1533, 1534, 1542, 1553, 1554, 1555, 1556, 1558, 1559, 1560, 1561, 1562, 1563, 1564, 1565, 1566, 1567, 1568, 1548, 1569, 1535, 1539, 1545, 1546, 1570, 1540, 1543, 1547, 1549, 1571, 1572, 1536, 1552, 1550, 1541, 1538, 1551, 1557, 1544

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + adenylosuccinate

649264, 651921, 652193, 652500, 649423, 649897, 651884, 652608, 649265, 649670, 650258, 652965, 653751, , 652929, 651925, 652347, 652356, 652812, 652317

1mez, 3D-view

6.3.4.4

ITP + IMP + L-Asp = IDP + phosphate + adenylosuccinate

1561,

1mez, 3D-view

6.3.4.4

ITP + IMP + L-aspartate = IDP + phosphate + adenylosuccinate

650258

1mez, 3D-view

6.3.4.4

UTP + IMP + L-Asp = UDP + phosphate + adenylosuccinate

1561

1mez, 3D-view

6.3.4.4

XTP + IMP + L-Asp = XDP + phosphate + adenylosuccinate

1561

1mez, 3D-view

6.3.4.4

GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP

, 652608

1mez, 3D-view

4.3.2.2

3 entries

6.3.4.4

10 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

6.3.4.4

-

1537, 1546, 1549, 649670, 652500

1mez, 3D-view

6.3.4.4

competitive inhibitor of IMP, noncompetitive inhibitor of GTP and aspartate

726945

1mez, 3D-view

6.3.4.4

competitive versus IMP, non-competitive versus GTP and aspartate

662801

1mez, 3D-view

6.3.4.4

competitive with respect to IMP

1548

1mez, 3D-view

6.3.4.4

feedback inhibition

652317

1mez, 3D-view

6.3.4.4

5 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (19 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (19 entries)

EC NUMBER

ENZYME 3D STRUCTURE

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

2ptr, 3D-view

4.3.2.2

2vd6, 3D-view

4.3.2.2

5nx9, 3D-view

4.3.2.2

18 entries

6.3.4.4

1mez, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (8 results)

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Show Turnover Number (8 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.3.2.2

0.00048

-

mutant T140A

682738

4.3.2.2

0.00689

-

mutant S306A

682738

4.3.2.2

0.01

-

mutant T93A

682738

4.3.2.2

0.1

-

pH 7.6, 37°C

729717

4.3.2.2

0.7

-

pH 7.6, 37°C

729717

4.3.2.2

1.14

-

mutant S94A

682738

4.3.2.2

1.74

-

wild-type enzyme

682738

4.3.2.2

7.5

-

pH 7.4, 25°C

691116

4.3.2.2

8 entries

K_M Value (42 results)

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Show KM Value (42 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

4.3.2.2

0.0012

-

-

34451

4.3.2.2

0.0013

-

mutant D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0014

-

recombinant His-tagged mutant R426H, pH 7.4, 25°C

729296

4.3.2.2

0.00146

-

histidine-tagged enzyme

682657

4.3.2.2

0.0015

-

mutant D69E

682733

4.3.2.2

0.0015

-

-

34449

4.3.2.2

0.00177

-

wild-type enzyme

682738

4.3.2.2

0.00178

-

none-tagged enzyme

682657

4.3.2.2

0.002

-

mutant D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0021

-

wild-type enzyme

682733

4.3.2.2

0.0021

-

recombinant His-tagged wild-type enzyme, pH 7.4, 25°C

729296

4.3.2.2

0.00224

-

mutant S94A

682738

4.3.2.2

0.00254

-

enzyme from cell line 1751

34462

4.3.2.2

0.0027

-

wild type, 50 mM HEPES, pH 7.0, 25°C

664041

4.3.2.2

0.0027

-

recombinant His-tagged mutant R303C, pH 7.4, 25°C

729296

4.3.2.2

0.00289

-

enzyme from cell line 1753

34462

4.3.2.2

0.0033

-

-

1541

4.3.2.2

0.0033

-

enzyme from wild-type cell lines

34462

4.3.2.2

0.004

-

50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0043

-

mutant I62E/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0046

-

mutant D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0047

-

-

34457

4.3.2.2

0.0061

-

mutant I62E/D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0071

-

mutant R310K

682733

4.3.2.2

0.0091

-

wild-type enzyme, pH 8.1, 37°C

730526

4.3.2.2

0.0093

-

mutant D69N

682733

4.3.2.2

0.0107

-

mutant I62D/D65R/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.012

-

-

34458

4.3.2.2

0.0128

-

mutant S306A

682738

4.3.2.2

0.013

-

-

34456

4.3.2.2

0.0166

-

mutant Q212E, 50 mM HEPES, pH 7.0, 25°C

664041

4.3.2.2

0.0175

-

mutant I62E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0177

-

mutant T93A

682738

4.3.2.2

0.0177

-

mutant I62D/D69E, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0181

-

mutant I62E/D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0192

-

mutant T140A

682738

4.3.2.2

0.023

-

mutant R310Q

682733

4.3.2.2

0.032

-

pH 7.4, 25°C

691116

4.3.2.2

0.0437

-

pH 7.6, 37°C

729717

4.3.2.2

0.0488

-

mutant I62D/D65R, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.0551

-

mutant I62D, 50 mM HEPES, pH 7.0, 25°C

665595

4.3.2.2

0.2042

-

pH 7.6, 37°C

729717

4.3.2.2

42 entries

K_i Value (7 results)

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Show KI Value (7 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

6.3.4.4

0.0094

-

pH 6.0, 70°C, competitive inhibition of IMP

726945

6.3.4.4

0.016

-

pH 6.7, 22°C, AdSS2

652500

6.3.4.4

0.021

-

pH 6.7, 22°C, AdSS1

652500

6.3.4.4

0.029

-

pH 7.5

662801

6.3.4.4

0.0426

-

pH 6.0, 70°C, noncompetitive inhibition of aspartate

726945

6.3.4.4

0.0429

-

pH 6.0, 70°C, noncompetitive inhibition of GTP

726945

6.3.4.4

2.7

-

pH 8.0, 25°C

649670

6.3.4.4

7 entries

References & Links

Literature References (97)

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Show Reference (97 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1533

3045328

Preliminary X-ray crystallographic study of adenylosuccinate synthetase from Escherichia coli

1988

Serra, M.A.; Bass, M.B.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

200

753-754

1534

3038024

Overproduction, purification, and characterization of adenylosuccinate synthetase from Escherichia coli

1987

Bass, M.B.; Fromm, H.J.; Stayton, M.M.

Arch. Biochem. Biophys.

256

335-342

1535

3542024

Isotope exchange at equilibrium studies with rat muscle adenylosauccinate synthetase

1986

Cooper, B.F.; Fromm, H.J.; Rudolph, F.B.

Biochemistry

25

7323-7327

1536

6703692

Adenylosuccinate synthetase from Dictyostelium discoideum: effects of hadacidin analogs and binding of [14C]hadacidin

1984

Jahngen, E.G.E.; Rossomando, E.F.

Arch. Biochem. Biophys.

229

145-154

1537

6347525

Regulation, genetics, and properties of adenylosuccinate synthetase

1983

Stayton, M.M.; Rudolph, F.B.; Fromm, H.J.

Curr. Top. Cell. Regul.

22

103-141

1538

6351751

Nitro analogs of substrates for adenylosuccinate synthetase and adenylosuccinate lyase

1983

Porter, D.J.T.; Rudie, N.G.; Bright, H.J.

Arch. Biochem. Biophys.

225

157-163

1539

7213642

Purification and properties of adenylosuccinate synthetase from Yoshida sarcoma ascites tumor cells

1980

Matsuda, Y.; Shimura, K.; Shiraki, H.; Nakagawa, H.

Biochim. Biophys. Acta

616

340-350

1540

529280

Preliminary crystallographic data for adenylosuccinate synthetase from rabbit skeletal muscle

1979

Harada, S.; Matsuura, Y.; Tanaka, N.; Kakudo, M.; Matsuda, Y.; Ogawa, H.; Shiraki, H.; Nakagawa, H.

J. Mol. Biol.

132

729-731

1541

468834

Specificity of adenylosuccinate synthetase and adenylosuccinate lyase from Leishmania donovani. Selective amination of an antiprotozoal agent

1979

Spector, T.; Jones, T.E.; Elion, G.B.

J. Biol. Chem.

254

8422-8426

1542

372184

Guanosine 5'-diphosphate-3'-diphosphate inhibition of adenylosuccinate synthetase

1979

Stayton, M.M.; Fromm, H.J.

J. Biol. Chem.

254

2579-2581

1543

692386

Adenylosuccinate synthetase (rabbit muscle, heart, and liver)

1978

Fischer, H.E.; Muirhead, K.M.; Bishop, S.H.

Methods Enzymol.

51

207-213

1544

21629

Adenylosuccinate synthetase from Azotobacter vinelandii: purification, properties and steady-state kinetics

1977

Markham, G.D.; Reed, G.H.

Arch. Biochem. Biophys.

184

24-35

1545

71897

Adenylosuccinate synthetase in rat liver: the existence of two types and their regulatory roles

1977

Matsuda, Y.; Ogawa, H.; Fukutome, S.; Shiraki, H.; Nakagawa, H.

Biochem. Biophys. Res. Commun.

78

766-771

1546

18452

Purification, crystallization, and properties of adenylosuccinate synthetase from rat skeletal muscle

1977

Ogawa, H.; Shiraki, H.; Matsuda, Y.; Kakiuchi, K.; Nakagawa, H.

J. Biochem.

81

859-869

1547

953040

Mammalian adenylosuccinate synthetase. Nucleotide monophosphate substrates and inhibitors

1976

Spector, T.; Miller, R.L.

Biochim. Biophys. Acta

445

509-517

1548

4436310

Human adenylosuccinate synthetase. Partial purification, kinetic and regulatory properties of the enzyme from placenta

1974

Van der Weyden, M.B.; Kelly, W.N.

J. Biol. Chem.

249

7282-7289

1549

4809527

Purification of adenylosuccinate synthetase from rabbit skeletal muscle

1974

Muirhead, K.M.; Bishop, S.H.

J. Biol. Chem.

249

459-464

1550

4708672

Regulation of the biosynthesis of purine nucleotides in Schizosaccharomyces pombe. II. Kinetic studies of adenylosuccinate synthetase

1973

Nagy, M.; Djembo-Taty, M.; Heslot, H.

Biochim. Biophys. Acta

309

1-10

1551

8790347

The mode of action and the structure of a herbicide in the complex with its target: binding of activated hydantocidin to the feedback regulation site of adenylosuccinate synthetase

1996

Fonne-Pfister, R.; Chemla, P.; Ward, E.; Girardet, M.; Kreuz, K.E.; Honzatko, R.B.; Fromm, H.J.; Schär, H.P.; Grutter, M.G.; Cowan-Jacob, S.W.

Proc. Natl. Acad. Sci. USA

93

9431-9436

1552

1989999

Purification and cDNA-derived sequence of adenylosuccinate synthetase from Dictyostelium discoideum

1991

Wiesmuller, L.; Wittbrodt, J.; Noegel, A.A.; Schleicher, M.

J. Biol. Chem.

266

2480-2485

1553

7490761

Refined crystal structure of unligated adenylosuccinate synthetase from Escherichia coli

1995

Silva, M.M.; Poland, B.W.; Hoffman, C.R.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

254

431-446

1554

9000627

Crystal structures of adenylosuccinate synthetase from Escherichia coli complexed with GDP, IMP hadacidin, NO3-, and Mg2+

1996

Poland, B.W.; Fromm, H.J.; Honzatko, R.B.

J. Mol. Biol.

264

1013-1027

1555

8703905

Involvement of arginine 143 in nucleotide substrate binding at the active site of adenylosuccinate synthetase from Escherichia coli

1996

Moe, O.A.; Baker-Malcolm, J.F.; Wang, W.; Kang, C.; Fromm, H.J.; Colman, R.F.

Biochemistry

35

9024-9033

1556

8179335

Characterization of the putative GTP-binding site residues of Escherichia coli adenylosuccinate synthetase by site-directed mutagenesis

1994

Kang, C.; Fromm, H.J.

Arch. Biochem. Biophys.

310

475-480

1557

8961938

Refined crystal structure of adenylsuccinate synthetase from Escherichia coli complexed with hydantocidin 5'-phosphate, GDP, HPO42-, Mg2+, and hadacidin

1996

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