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Ligand histamine

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

histidine metabolism

KEGG

Asthma, Biosynthesis of alkaloids derived from histidine and purine, Biosynthesis of secondary metabolites, Fc epsilon RI signaling pathway, Gastric acid secretion, Histamine H2/H3 receptor agonists/antagonists, Histidine metabolism, Inflammatory mediator regulation of TRP channels, Neuroactive ligand-receptor interaction, Protein digestion and absorption, Synaptic vesicle cycle more

MetaCyc

acinetobactin biosynthesis, anguibactin biosynthesis, histamine biosynthesis, histamine degradation, pseudomonine biosynthesis

Show all BRENDA pathways known for histamine

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.22

histamine + H2O + O2 = (imidazol-4-yl)acetaldehyde + NH3 + H2O2

725767, 741567, 742953, 742417, 743259, 723927, 741597, 741656, 724291, 725736

-

1.4.3.4

histamine + H2O + O2 = 1H-imidazol-4-ylacetaldehyde + NH3 + H2O2

725620

-

1.4.3.4

histamine + H2O + O2 = ?

711832

-

1.4.3.4

2 entries

2.3.1.87

acetyl-CoA + histamine = CoA + N-acetylhistamine

720933

-

6.3.2.18

ATP + L-glutamate + histamine = products of ATP breakdown + Nalpha-gamma-L-glutamylhistamine

1102

-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.22

L-histidin = histamine + CO2

650807

-

4.1.1.22

L-histidine = histamine + CO2

651193, 651196, 651498, 652237, , 649295, 651162, 651497, 652502, 653860, 653861, 653849, 649384, 651607, 652849

-

4.1.1.22

2 entries

Substrate in Enzyme-catalyzed Reactions (26 results)

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Show Substrate (26 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.99.52

histamine + L-cysteine + O2 = S-(histamin-5-yl)-L-cysteine S-oxide + H2O

733647

-

1.4.3.10

histamine + O2 + H2O = 1H-imidazol-4-ylacetaldehyde + NH3 + H2O2

724877

-

1.4.3.10

histamine + O2 + H2O = ?

395442, 395444

-

1.4.3.10

2 entries

1.4.3.13

histamine + O2 + H2O = ?

671973

-

1.4.3.21

histamine + H2O + O2 = (imidazol-4-yl)acetaldehyde + NH3 + H2O2

687459, 724537

-

1.4.3.21

histamine + H2O + O2 = 1H-imidazol-4-ylacetaldehyde + NH3 + H2O2

725733, 742881, 742933

-

1.4.3.21

histamine + H2O + O2 = ?

726536

-

1.4.3.22

histamine + H2O + O2 = (imidazol-4-yl)acetaldehyde + NH3 + H2O2

391941, 391922, 391923, 656295, 725767, 741567, 742953, 391918, 391920, 391953, 742417, 743259, 723927, 741597, 741656, 391945, 656323, 655478, 688193, 391951, 724291, 725736, 391947, 720756

-

1.4.3.22

histamine + H2O + O2 = ?

742953

-

1.4.3.22

histamine + O2 + H2O = (imidazol-4-yl)acetaldehyde + NH3 + H2O2

672492

-

1.4.3.4

histamine + H2O + O2 = 1H-imidazol-4-ylacetaldehyde + NH3 + H2O2

725621, 725620, 672492

-

1.4.3.4

histamine + H2O + O2 = ?

711832, 672492

-

1.4.3.4

histamine + O2 + H2O = 1H-imidazol-4-ylacetaldehyde + NH3 + H2O2

672492

-

1.4.3.21

3 entries

1.4.3.22

3 entries

1.4.3.4

3 entries

1.4.9.1

histamine + acceptor + H2O = ? + NH3 + reduced acceptor

396587

-

1.4.9.2

histamine + H2O + 2,6-dichlorophenol indophenol = 1H-imidazol-4-ylacetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol

655062

-

2.1.1.8

S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + N-methylhistamine

686558

1jqd, 3D-view

2.1.1.8

S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine

441556, 441565, 441570, 441571, 441575, 441564, 441559, 701604, 703430, 441560, 441561, 441562, 441566, 441568, 441572, 441574, 441558, 441569, 661881, 441563, 691489, 675356, 756090, 441557, 441573, 441567, 677114

1jqd, 3D-view

2.1.1.8

2 entries

2.3.1.5

acetyl-CoA + histamine = CoA + N-acetylhistamine

487121, 487628, 487125, 487116

-

2.3.1.57

acetyl-CoA + histamine = CoA + N-acetylhistamine

487260

-

2.3.1.87

acetyl-CoA + histamine = CoA + N-acetylhistamine

735681, 735933, 720933, 758432

-

2.3.1.87

butanoyl-CoA + histamine = CoA + N-butanoylhistamine

735681

-

2.3.1.87

hexanoyl-CoA + histamine = CoA + N-hexanoylhistamine

735681

-

2.3.1.87

propionyl-CoA + histamine = CoA + N-propionylhistamine

758432

-

2.3.2.13

histamine + acetyl-alphaS1-casein = ?

487855

-

2.3.2.13

histamine + maleyl-bovine serum albumin = ?

487855

-

2.3.1.87

4 entries

2.3.2.13

2 entries

6.3.2.18

ATP + L-glutamate + histamine = products of ATP breakdown + Nalpha-gamma-L-glutamylhistamine

1102

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.22

L-His = Histamine + CO2

4142, 4151, 4155, 4156, 4158, 4163, 4164, 4165, 4144, 4147, 4149, 4160, 4161, 4162, 4154, 4159, 4138, 4139, 4140, 4141, 4146, 4152, 4166, 4167, 4148, 4143, 4150, 4153, 4157, 4145

-

4.1.1.22

L-histidin = histamine + CO2

650807

-

4.1.1.22

L-histidine = histamine + CO2

651193, 651196, 651498, 652237, , 649295, 651162, 651497, 652502, 653860, 653861, 653849, 649384, 651607, 652849

-

4.1.1.22

3 entries

4.1.1.53

Histidine = Histamine + CO2

-

-

Activator in Enzyme-catalyzed Reactions (13 results)

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Show Activating Compound (13 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.5

10 microM

695572

-

2.7.1.91

0.001 mM, up to 5fold increase of activity after 20 h

672377

-

2.7.4.1

-

645113

-

3.1.3.11

5 mM, increases activity by about 200%

170759

-

3.1.4.4

evokes a transient increase in intraendothelial Ca2+-concentration and enhancey PLD activity significantly. A significant fraction of PLD1 translocates to the plasma membrane after 5 min of histamine stimulation of HUVECs

691465

-

3.2.1.4

20 mM, stimulates

393594

-

3.5.3.12

at concentration of 0.1 g/l about 2% more putrescine production, at concentration of 1 g/l about 5% more putrescine production

692430

-

3.5.3.12

at concentration of 0.1 g/l and 1.0 g/l about 10% more putrescine production

692430

-

3.5.3.12

2 entries

3.5.3.18

activating ability in decreasing order: histamine, imidazole, L-histidine, D-histidine

652188

-

4.2.1.1

-

696635, 714441, 716412, 696648, 702675

1avn, 3D-view

4.2.1.1

activation constant of 0.0274 mM

702616

1avn, 3D-view

4.2.1.1

activation constant of 0.12 mM

702683

1avn, 3D-view

4.2.1.1

enzyme bound structure, PDB ID 1AVN

748692

1avn, 3D-view

4.2.1.1

4 entries

Inhibitor in Enzyme-catalyzed Reactions (25 results)

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Show Inhibitors (25 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.23

competitive inhibition

286330

1kar, 3D-view

1.4.3.21

substrate inhibition; substrate inhibition

726536

-

1.4.3.22

-

391925, 391935, 391943

-

1.4.3.22

substrate inhibition

725736

-

1.4.3.22

2 entries

1.4.9.2

weak substrate inhibition above 1 mM

655062

-

2.1.1.8

-

441561

1jqd, 3D-view

2.1.1.8

0.025-0.1 mM

441559

1jqd, 3D-view

2.1.1.8

not

441567

1jqd, 3D-view

2.1.1.8

3 entries

2.3.1.97

noncompetitive

487770

-

2.3.2.13

-

672389

-

2.3.2.5

-

659288

-

2.4.2.36

250 mM, almost complete inhibition

489798

-

2.7.1.35

-

641409

-

3.2.1.14

-

393487, 393503

-

3.2.1.17

-

171040, 171072, 171086

-

3.4.14.2

-

679288

-

3.4.14.2

0.1 M 55% inhibition

95234

-

3.4.14.2

2 entries

3.4.21.59

-

29387

-

3.5.4.8

less effective inhibitor

209717

-

4.1.1.17

-

4024

-

4.1.1.22

-

4148, 4166

-

4.1.1.22

at high concentrations

4145

-

4.1.1.22

2 entries

4.1.1.28

1% inhibition at 4 mM

743978

-

4.2.1.1

-

702687

1avn, 3D-view

6.3.4.19

-

704642

-

3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (5 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.23

1kar, 3D-view

1.7.6.1

4xmf, 3D-view

2.1.1.8

1jqd, 3D-view

3.4.21.4

3rxh, 3D-view

4.2.1.1

1avn, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (22 results)

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Show Turnover Number (22 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.99.52

0.36

-

pH 8.0, 26°C

733647

1.4.3.21

0.46

-

isoform AMAO3, in 100 mM potassium phosphate buffer (pH 7.0), at 37°C

726536

1.4.3.21

1.8

-

in 50 mM Tris-HCl buffer, pH 8.0, at 25°C

724537

1.4.3.21

5.91

-

isoform AMAO2, in 100 mM potassium phosphate buffer (pH 7.0), at 37°C

726536

1.4.3.21

13.2

-

isoform AO2, in 200 mM potassium phosphate buffer pH 7.6, at 30°C

725733

1.4.3.22

2.93

-

pH 8.5, 25°C

688193

1.4.3.22

10.3

-

pH 7.2, 25°C

655478, 688193

1.4.3.22

95

-

-

391951

1.4.3.22

8340

-

pH 7.2, 37°C

656295

2.3.1.87

0.1

-

cosubstrate hexanoyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

0.48

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

0.5

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

0.87

-

cosubstrate butanoyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

1.39

-

mutant E26A, pH 8.0, 22°C

735681

2.3.1.87

1.9

-

mutant T167A, pH 8.0, 22°C

735681

2.3.1.87

2.2

-

mutant T167A/S171A, pH 8.0, 22°C

735681

2.3.1.87

7.7

-

mutant H206A, pH 8.0, 22°C

735681

2.3.1.87

10.4

-

mutant S171A, pH 8.0, 22°C

735681

2.3.1.87

30

-

cosubstrate acetyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

71

-

mutant R138A, pH 8.0, 22°C

735681

4.2.1.1

380000

-

at 25°C, pH 8.3 in 20 mM Tris buffer and 20 mM NaClO4

702616

4.2.1.1

1070000

-

at 25°C, pH 8.3 in 20 mM Tris buffer and 20 mM NaClO4, in the presence of 0.01 mM histamine

702616

1.4.3.21

4 entries

1.4.3.22

4 entries

2.3.1.87

11 entries

4.2.1.1

2 entries

K_M Value (52 results)

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Show KM Value (52 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.99.52

0.23

-

pH 8.0, 26°C

733647

1.4.3.21

0.28

-

isoform AO2, in 200 mM potassium phosphate buffer pH 7.6, at 30°C

725733

1.4.3.21

0.41

-

isoform AMAO2, in 100 mM potassium phosphate buffer (pH 7.0), at 37°C

726536

1.4.3.21

0.7

-

in 50 mM Tris-HCl buffer, pH 8.0, at 25°C

724537

1.4.3.21

0.88

-

isoform AMAO3, in 100 mM potassium phosphate buffer (pH 7.0), at 37°C

726536

1.4.3.22

0.0028

-

pH 7.2, 37°C

656295

1.4.3.22

0.013

-

free enzyme

391920

1.4.3.22

0.0172

-

-

391947

1.4.3.22

0.019

-

-

391922

1.4.3.22

0.035

-

in 100 mM potassium phosphate, pH 7.2, at 37°C

725736

1.4.3.22

0.065

-

at pH 7.4

391918

1.4.3.22

0.083

-

at pH 6.3

391918

1.4.3.22

0.091

-

pH 8.5, 25°C

688193

1.4.3.22

0.108

-

enzyme from seminal plasma, at 37°C, pH not specified in the publication

725767

1.4.3.22

0.112

-

free enzyme, in 0.1 M phosphate buffer, pH 7.4, at 25°C

723927

1.4.3.22

0.124

-

enzyme from placenta, at 37°C, pH not specified in the publication

725767

1.4.3.22

0.17

-

at pH 8.5

391918

1.4.3.22

0.51

-

pH 7.0, 37°C

656323

1.4.3.22

0.6

-

-

391951

1.4.3.22

0.79

-

pH 7.2, 25°C

688193

1.4.3.22

1.05

-

immobilized enzyme, apparent value, in 0.1 M phosphate buffer, pH 7.4, at 25°C

723927

1.4.3.22

1.8

-

immobilized enzyme

391920

1.4.3.4

3.6

-

in 0.01 M phosphate buffer, pH 7.4, at 23°C

725620

1.4.3.4

5.61

-

pH not specified in the publication, temperature not specified in the publication

711832

1.4.3.21

4 entries

1.4.3.22

17 entries

1.4.3.4

2 entries

1.4.9.2

0.171

-

pH 7.5, 30°C

655062

2.1.1.8

0.0011

-

mutant L208V, pH 8.0, 25°C

756090

2.1.1.8

0.0019

-

wild-type, pH 8.0, 25°C

756090

2.1.1.8

0.0034

-

mutant L208F, pH 8.0, 25°C

756090

2.1.1.8

0.0042

-

-

441559

2.1.1.8

0.0061

-

-

441561

2.1.1.8

0.012

-

-

441566

2.1.1.8

0.014

-

-

441570

2.1.1.8

0.026

-

-

441564

2.1.1.8

0.035

-

-

441556, 441557

2.1.1.8

0.043

-

-

441573

2.1.1.8

10 entries

2.3.1.5

0.72

-

-

487116

2.3.1.87

0.0023

-

mutant H206A, pH 8.0, 22°C

735681

2.3.1.87

0.0034

-

mutant S171A, pH 8.0, 22°C

735681

2.3.1.87

0.0049

-

mutant R138A, pH 8.0, 22°C

735681

2.3.1.87

0.0067

-

mutant T167A, pH 8.0, 22°C

735681

2.3.1.87

0.013

-

mutant T167A/S171A, pH 8.0, 22°C

735681

2.3.1.87

0.016

-

mutant E26A, pH 8.0, 22°C

735681

2.3.1.87

0.52

-

cosubstrate acetyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

1.92

-

pH 7.5, 22°C

735933

2.3.1.87

2.8

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

2.9

-

cosubstrate butanoyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

15

-

cosubstrate hexanoyl-CoA, wild-type, pH 8.0, 22°C

735681

2.3.1.87

16

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.2.13

0.38

-

recombinant enzyme

487855

2.3.2.13

0.52

-

native enzyme

487855

2.3.1.87

12 entries

2.3.2.13

2 entries

4.2.1.1

7.9

-

at 25°C, pH 8.3 in 20 mM Tris buffer and 20 mM NaClO4

702616

6.3.2.18

0.653

-

at pH 8.0 and 37°C

1102

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

1.4.3.21

3.51

-

isoform AMAO2, in 100 mM potassium phosphate buffer (pH 7.0), at 37°C

726536

1.4.3.22

0.83

-

-

391943

1.4.3.22

6

-

-

391935

1.4.3.22

17

-

-

391925

1.4.3.22

30

-

pH and temperature not specified in the publication

725736

1.4.3.22

4 entries

2.3.2.5

0.85

-

30°C, pH 8.0

659288

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

6.3.4.19

0.33

-

pH 8.5, 21°C

704642

References & Links

Literature References (163)

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Show Reference (163 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1102

6125565

An in vitro characterization of gamma-glutamylhistamine synthetase: a novel enzyme catalyzing histamine metabolism in the central nervous system of the marine mollusk, Aplysia californica

1982

Stein, C.; Weinreich, D.

J. Neurochem.

38

204-214

4024

5073764

Studies on ornithine decarboxylase from the liver of thioacetamide-treated rats

1972

Ono, M.; Inoue, H.; Suzuki, F.; Takeda, Y.

Biochim. Biophys. Acta

284

285-297

4138

37890

Histidine decarboxylase from Lactobacillus 30a: reconstitution from separated subunits

1979

Yamagata, S.; Snell, E.E.

Biochemistry

18

2964-2967

4139

7451468

Crystallization and subunit structure of histidine decarboxylase from Lactobacillus 30a

1981

Hackert, M.L.; Meador, W.E.; Oliver, R.M.; Salmon, J.B.

J. Biol. Chem.

256

687-690

4140

4009714

Structure determination of histidine decarboxylase from Lactobacillus 30a at 3.0 A resolution

1985

Parks, E.H.; Ernst, S.R.; Hamlin, R.; Xuong, N.H.; Hackert, M.L.

J. Mol. Biol.

182

455-465

4141

-

Histidine decarboxylase (Lactobacillus 30a)

1971

Chang, G.W.; Snell, E.E.

Methods Enzymol.

17B

663-667

4142

-

Histidine decarboxylase (mammalian)

1971

Aures, D.; Hakanson, R.

Methods Enzymol.

17B

667-677

4143

4829439

Separation and characterisation of subunits of histidine decarboxylase from Micrococcus sp. n

1974

Prozorovski, V.; Jornvall, H.

Eur. J. Biochem.

42

405-409

4144

6778871

Histidine decarboxylase. Purification from fetal rat liver, immunologic properties, and histochemical localization in brain and stomach

1981

Tran, V.T.; Snyder, S.H.

J. Biol. Chem.

256

680-686

4145

7075603

Properties of histidine decarboxylase from rat gastric mucosa

1982

Savany, A.; Cronenberger, L.

Eur. J. Biochem.

123

593-599

4146

7085622

Histidine decarboxylase from Lactobacillus 30a. Comparative properties of wild type and mutant proenzymes and their derived enzymes

1982

Recsei, P.A.; Snell, E.E.

J. Biol. Chem.

257

7196-7202

4147

7138509

Isolation and properties of multiple forms of histidine decarboxylase from rat gastric mucosa

1982

Savany, A.; Cronenberger, L.

Biochem. J.

205

405-412

4148

6294108

Pyruvoyl-dependent histidine decarboxylase from Clostridium perfringens and Lactobacillus buchneri

1983

Rescei, P.A.; Moore, W.M.; Snell, E.E.

J. Biol. Chem.

258

439-444

4149

6425286

Purification of histidine decarboxylase from the liver of fetal rats and its immunochemical and immunohistochemical characterization

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Nanoscale enzyme inhibitors: fullerenes inhibit carbonic anhydrase by occluding the active site entrance

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Putrescine biosensor based on putrescine oxidase from Kocuria rosea

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Substrate specificity of an oxygen dependent sulfoxide synthase in ovothiol biosynthesis

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Links to other databases for histamine

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