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Ligand 1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide

Basic Ligand Information

Molecular Structure

Show all BRENDA pathways known for 1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (15 results)

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Show Natural Substrate (15 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5a5w, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5abt, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5ahf, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5ahi, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5g4w, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237

5a5w, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237

5abt, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237

5ahf, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237

5ahi, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237

5g4w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5a5w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5abt, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5ahf, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5ahi, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5g4w, 3D-view

5.3.1.16

15 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.4.19

1-(5-phosphoribosyl)-AMP + H2O = 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide

0

-

Substrate in Enzyme-catalyzed Reactions (25 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5a5w, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5abt, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5ahf, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5ahi, 3D-view

5.3.1.16

1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxy-D-ribulos-1-ylamino)methylideneamino]-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide

728586

5g4w, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237, 677012

5a5w, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237, 677012

5abt, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237, 677012

5ahf, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237, 677012

5ahi, 3D-view

5.3.1.16

1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide = 5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide

653237, 677012

5g4w, 3D-view

5.3.1.16

N'-[(5'-phosphoribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleotide = ?

648892

5a5w, 3D-view

5.3.1.16

N'-[(5'-phosphoribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleotide = ?

648892

5abt, 3D-view

5.3.1.16

N'-[(5'-phosphoribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleotide = ?

648892

5ahf, 3D-view

5.3.1.16

N'-[(5'-phosphoribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleotide = ?

648892

5ahi, 3D-view

5.3.1.16

N'-[(5'-phosphoribosyl)formimino]-5-aminoimidazole-4-carboxamide ribonucleotide = ?

648892

5g4w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5a5w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5abt, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5ahf, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5ahi, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = ?

2641, 2642

5g4w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = N-(5'-Phospho-D-1-ribulosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide

2641, 2643

5a5w, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = N-(5'-Phospho-D-1-ribulosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide

2641, 2643

5abt, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = N-(5'-Phospho-D-1-ribulosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide

2641, 2643

5ahf, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = N-(5'-Phospho-D-1-ribulosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide

2641, 2643

5ahi, 3D-view

5.3.1.16

N-(5'-Phospho-D-ribosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide = N-(5'-Phospho-D-1-ribulosylformimino)-5-amino-1-(5''-phospho-D-ribosyl)-4-imidazolecarboxamide

2641, 2643

5g4w, 3D-view

5.3.1.16

25 entries

Product in Enzyme-catalyzed Reactions (2 results)

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Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.4.19

1-(5-phospho-beta-D-ribosyl)-AMP + H2O = 1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide

0

-

3.5.4.19

1-(5-phosphoribosyl)-AMP + H2O = 1-(5-phosphoribosyl)-5-[(5-phosphoribosylamino)methylideneamino]imidazole-4-carboxamide

0

-

3.5.4.19

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

4.3.2.10

binding of the allosteric effector ligand stimulates millisecond timescale motions in the enzyme that enhance its catalytic function. The flexibility of the apo enzyme is nearly identical to that of its N'-[(5'-phosphoribulosyl)formimino]-5-aminoimidazole-4-carboxamide-ribonucleotide activated state at 70°C, whereas conformational motions are considerably different between the two forms of the enzyme at room temperature. Allosteric activation by N'-[(5'-phosphoribulosyl)formimino]-5-aminoimidazole-4-carboxamide-ribonucleotide decreases to 65fold at 70°C, compared to 4200fold at 30°C

747861

7ac8, 3D-view

3D Structure of Enzyme-Ligand-Complex (PDB) (52 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (52 entries)

EC NUMBER

ENZYME 3D STRUCTURE

3.5.1.2

7ac8, 3D-view

4.3.2.10

7ac8, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

5a5w, 3D-view

5.3.1.16

5abt, 3D-view

5.3.1.16

5ahf, 3D-view

5.3.1.16

5ahi, 3D-view

5.3.1.16

5g4w, 3D-view

5.3.1.16

50 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (12 results)

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Show Turnover Number (12 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

5.3.1.16

0.00027

-

25°C, pH 7.5, mutant enzyme D127N

648892

5.3.1.16

0.018

-

25°C, pH 7.5, mutant enzyme T164A

648892

5.3.1.16

0.23

-

25°C, pH 7.5, mutant enzyme R83N

648892

5.3.1.16

0.29

-

25°C, pH 7.5, mutant enzyme D51N

648892

5.3.1.16

0.38

-

25°C, pH 7.5, mutant enzyme H48A

648892

5.3.1.16

0.67

-

25°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

1.54

-

37°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

2.94

-

37°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

4.9

-

25°C, pH 7.5

648892

5.3.1.16

6.08

-

25°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

14.3

-

37°C, pH 7.5

648892

5.3.1.16

32

-

80°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

12 entries

K_M Value (8 results)

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Show KM Value (8 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

5.3.1.16

0.6

-

25°C or 37°C, pH 7.5, wild-type enzyme

648892

5.3.1.16

1.6

-

25°C, pH 7.5

648892

5.3.1.16

1.8

-

37°C, pH 7.5

648892

5.3.1.16

2

-

25°C, pH 7.5, mutant enzyme D127N

648892

5.3.1.16

2.9

-

25°C, pH 7.5, mutant enzyme H48A

648892

5.3.1.16

5.6

-

25°C, pH 7.5, mutant enzyme T164A

648892

5.3.1.16

6.4

-

25°C, pH 7.5, mutant enzyme D51N

648892

5.3.1.16

37.9

-

25°C, pH 7.5, mutant enzyme R83N

648892

5.3.1.16

8 entries

References & Links

Literature References (8)

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Show Reference (8 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2641

-

Enzymes and intermediates of histidine biosynthesis in Salmonella typhimurium

1971

Martin, R.G.; Berberich, M.A.; Ames, B.N.; Davis, W.W.; Goldberger, R.F.; Yourno, J.D.

Methods Enzymol.

17B

3-44

2642

4959618

Physical and chemical characterization of the isomerase of histidine biosynthesis in Salmonella typhimurium

1967

Margolies, M.N.; Goldberger, R.F.

J. Biol. Chem.

242

256-264

2643

5330429

Isolation of the fourth enzyme (isomerase) of histidine biosynthesis from Salmonella typhimurium

1966

Margolies, M.N.; Goldberger, R.F.

J. Biol. Chem.

241

3262-3269

648892

12356303

Two (betaalpha)8-barrel enzymes of histidine and tryptophan biosynthesis have similar reaction mechanisms and common strategies for protecting their labile substrates

2002

Henn-Sax, M.; Thoma, R.; Schmidt, S.; Hennig, M.; Kirschner, K.; Sterner, R.

Biochemistry

41

12032-12042

653237

9747713

Molecular cloning and characterization of the gene encoding N'-[(5'-phosphoribosyl)-formimino]-5-aminoimidazole-4-carboxamide ribonucleotide (BBM II) isomerase from Arabidopsis thaliana

1998

Fujimori, K.; Tada, S.; Kanai, S.; Ohta, D.

Mol. Gen. Genet.

259

216-223

677012

16731983

Crystal structure of the yeast His6 enzyme suggests a reaction mechanism

2006

Quevillon-Cheruel, S.; Leulliot, N.; Graille, M.; Blondeau, K.; Janin, J.; van Tilbeurgh, H.

Protein Sci.

15

1516-1521

728586

23133571

Perturbations in histidine biosynthesis uncover robustness in the metabolic network of Salmonella enterica

2012

Koenigsknecht, M.J.; Lambrecht, J.A.; Fenlon, L.A.; Downs, D.M.

PLoS ONE

7

e48207

747861

29468164

Glutamine hydrolysis by imidazole glycerol phosphate synthase displays temperature dependent allosteric activation

2018

Lisi, G.; Currier, A.; Loria, J.

Front. Mol. Biosci.

5

4

Links to other databases for 1-(5-phospho-beta-D-ribosyl)-5-[(5-phospho-beta-D-ribosylamino)methylideneamino]imidazole-4-carboxamide

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Show Links (1 entry)

ChEBI

PubChem