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Ligand tryptamine

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

tryptophan metabolism

KEGG

Biosynthesis of alkaloids derived from shikimate pathway, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, Indole alkaloid biosynthesis, Neuroactive ligand-receptor interaction, Tryptophan metabolism more

MetaCyc

beta-carboline biosynthesis, hydroxycinnamic acid serotonin amides biosynthesis, indole-3-acetate biosynthesis II, L-tryptophan degradation VI (via tryptamine), L-tryptophan degradation X (mammalian, via tryptamine), psilocybin biosynthesis, secologanin and strictosidine biosynthesis more

Show all BRENDA pathways known for tryptamine

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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

1.13.11.52

tryptamine + O2 = ?

712947, 663564, 712694

-

1.14.99.59

tryptamine + reduced acceptor + O2 = 4-hydroxytryptamine + acceptor + H2O

744033

-

1.4.3.21

tryptamine + H2O + O2 = (1H-indol-3-yl)acetaldehyde + NH3 + H2O2

742600, 703130

-

1.4.3.4

tryptamine + H2O + O2 = (1H-indol-3-yl)acetaldehyde + NH3 + H2O2

711832

-

1.4.3.4

tryptamine + H2O + O2 = 1-H-indol-3-yl-acetaldehyde + NH3 + H2O2

725620

-

1.4.3.4

2 entries

2.3.1.87

acetyl-CoA + tryptamine = CoA + N-acetyltryptamine

719583

-

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine

648725, 648726, 393871, 648717, 648723, 648713, 648714, 648715, 648716, 648718, 648720, 648721, 648728, 648729, 648719, 648722, 648730, 648727

2fpb, 3D-view

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine + H2O

729484, 695121, 694743, 729396

2fpb, 3D-view

4.3.3.2

2 entries

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

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.1.1.105

L-tryptophan = tryptamine + CO2

653508, 0

-

4.1.1.28

L-Trp = Tryptamine + CO2

0

-

4.1.1.28

L-tryptophan = tryptamine + CO2

653352, 653356, 650868, 653366, 649601, 649696, 650410, 653443, 651068, 0, 650436, 650450, 653288, 653528, 651417

-

4.1.1.28

Tryptophan = Tryptamine + CO2

0

-

4.1.1.28

3 entries

4.3.3.2

3-alpha(S)-strictosidine + H2O = tryptamine + secologanin

0

2fpb, 3D-view

Substrate in Enzyme-catalyzed Reactions (53 results)

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Show Substrate (53 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.2.2

tryptamine + H2O2 = ?

671909

-

1.13.11.52

tryptamine + O2 = ?

395472, 671714, 696151, 712947, 395459, 395462, 663564, 712694

-

1.13.11.52

tryptamine + O2- = ?

665454

-

1.13.11.52

2 entries

1.13.99.3

tryptamine + O2 = ?

439304, 439307

-

1.14.19.9

tryptamine + FADH2 + Cl- + O2 + H+ = 7-chloro-L-tryptamine + FAD + H2O

727668

7ju0, 3D-view

1.14.99.59

tryptamine + reduced acceptor + O2 = 4-hydroxytryptamine + acceptor + H2O

744033

-

1.4.3.10

tryptamine + O2 + H2O = 1H-indol-3-yl-acetaldehyde + NH3 + H2O2

724877

-

1.4.3.21

tryptamine + H2O + O2 = (1H-indol-3-yl)acetaldehyde + NH3 + H2O2

743594, 742600, 703130, 742933

-

1.4.3.21

tryptamine + H2O + O2 = 1H-indol-3-ylacetaldehyde + NH3 + H2O2

676364

-

1.4.3.22

tryptamine + H2O + O2 = 1H-indol-3-ylacetaldehyde + NH3 + H2O2

765126, 656323, 672497

-

1.4.3.22

tryptamine = ?

391941, 391951

-

1.4.3.4

tryptamine + H2O + O2 = (1H-indol-3-yl)acetaldehyde + NH3 + H2O2

711832

-

1.4.3.4

tryptamine + H2O + O2 = 1-H-indol-3-yl-acetaldehyde + NH3 + H2O2

394556, 394562, 706934, 725620, 725619

-

1.4.3.4

tryptamine + H2O + O2 = 1H-indol-3-yl-acetaldehyde + NH3 + H2O2

394560, 394557, 394548, 394580

-

1.4.3.4

tryptamine + H2O + O2 = ?

675787, 742990, 742989

-

1.4.3.21

2 entries

1.4.3.22

2 entries

1.4.3.4

4 entries

1.4.9.1

tryptamine + acceptor + H2O = ?

686104

-

1.4.9.2

tryptamine + acceptor + H2O = 1H-indole-3-acetaldehyde + NH3 + reduced acceptor

396589, 685206, 396591

-

1.4.9.2

tryptamine + H2O + 2,6-dichlorophenol indophenol = 4H-indol-3-yl-acetaldehyde + NH3 + reduced 2,6-dichlorophenol indophenol

655062

-

1.4.9.2

2 entries

1.5.3.16

tryptamine + O2 + H2O = ?

690790

-

1.5.3.17

tryptamine + O2 + H2O = ?

690790

-

2.1.1.49

S-adenosyl-L-methionine + tryptamine = S-adenosyl-L-homocysteine + alpha-N-methyltryptamine

441353, 441356, 441352, 441354

-

2.3.1.110

4-coumaroyl-CoA + tryptamine = CoA + N-(4-coumaroyl)tryptamine

720789

-

2.3.1.110

caffeoyl-CoA + tryptamine = CoA + N-caffeoyltryptamine

660244

-

2.3.1.110

feruloyl-CoA + tryptamine = CoA + feruloyltryptamine

486130, 676598

-

2.3.1.110

3 entries

2.3.1.5

acetyl-CoA + tryptamine = CoA + N-acetyltryptamine

487120, 487123, 487628, 487105, 487116, 487122, 487126

-

2.3.1.87

acetyl-CoA + tryptamine = CoA + N-acetyltryptamine

487126, 675544, 487637, 735681, 487644, 720316, 487105, 487123, 487621, 487622, 487629, 659760, 686212, 487631, 719595, 758432, 487634, 720470, 487632, 487623, 487646, 658469, 719583, 675629, 658812, 672840, 674418, 704421, 673165, 736685, 735981, 757480, 756913

-

2.3.1.87

acetyl-CoA + tryptamine = N-acetyltryptamine + CoA

660381

-

2.5.1.34

dimethylallyl diphosphate + tryptamin = ?

684649

-

2.5.1.34

dimethylallyl diphosphate + tryptamin = diphosphate + 4-(3-methylbut-2-enyl)-tryptamin

673088

-

2.5.1.34

dimethylallyl diphosphate + tryptamine = ?

701952

-

2.5.1.34

dimethylallyl diphosphate + tryptamine = diphosphate + 4-(3-methylbut-2-enyl)-tryptamine

684649, 737837

-

2.5.1.80

dimethylallyl diphosphate + tryptamine = ?

701952

-

2.5.1.80

dimethylallyl diphosphate + tryptamine = diphosphate + 7-(3-methylbut-2-enyl)-tryptamine

737837, 684649

-

4.3.3.2

methyl (2R,4S)-2-(2-methylpropoxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2R,4S)-2-(2-methylpropoxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2R,4S)-2-(cyclohexyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2R,4S)-2-(cyclohexyloxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2R,4S)-2-ethoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2R,4S)-2-ethoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2R,4S)-2-tert-butoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2R,4S)-2-tert-butoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2S,4S)-2-(2-methylpropoxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2S,4S)-2-(2-methylpropoxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2S,4S)-2-ethoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2S,4S)-2-ethoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

methyl (2S,4S)-2-tert-butoxy-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate + tryptamine = methyl (2S,4S)-2-tert-butoxy-4-[(1S)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate + H2O

706802

2fpb, 3D-view

4.3.3.2

secologanin + tryptamine = 3-alpha(S)-strictosidine + H2O

706802

2fpb, 3D-view

4.3.3.2

tryptamine + 2'-O-methylsecologanin = ?

648713

2fpb, 3D-view

4.3.3.2

tryptamine + 2'-O-methylsecologanin = ? + H2O

694743

2fpb, 3D-view

4.3.3.2

tryptamine + 3'-O-methylsecologanin = ?

648713

2fpb, 3D-view

4.3.3.2

tryptamine + 3'-O-methylsecologanin = ? + H2O

694743

2fpb, 3D-view

4.3.3.2

tryptamine + dihydrosecologanin = ?

648713

2fpb, 3D-view

4.3.3.2

tryptamine + secologanic acid allyl ester = ? + H2O

694743

2fpb, 3D-view

4.3.3.2

tryptamine + secologanic acid pentynyl ester = ? + H2O

694743

2fpb, 3D-view

4.3.3.2

tryptamine + secologanic acid propynyl ester = ? + H2O

694743

2fpb, 3D-view

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine

648723, 648714, 648715, 648716, 648718, 648720, 648721, 648725, 648726, 648728, 648729, 648713, 393871, 648719, 648722, 648717, 648730, 715978, 648727, 694743

2fpb, 3D-view

4.3.3.2

tryptamine + secologanin = 3-alpha(S)-strictosidine + H2O

664326, 729396, 729484, 695121, 694743, 703154

2fpb, 3D-view

4.3.3.2

tryptamine + secologanin = 3alpha(S)-strictosidine

663507, 664183, 666582

2fpb, 3D-view

4.3.3.2

tryptamine + secologanin = ? + H2O

716888

2fpb, 3D-view

2.3.1.87

2 entries

2.5.1.34

4 entries

2.5.1.80

2 entries

4.3.3.2

20 entries

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.5

N-phosphopyridoxyl tryptamine + H2O + O2 = pyridoxal 5'-phosphate + tryptamine + H2O2

391879

-

4.1.1.105

L-tryptophan = tryptamine + CO2

653508, 0

-

4.1.1.28

L-Trp = Tryptamine + CO2

0, 4202

-

4.1.1.28

L-tryptophan = tryptamine + CO2

653352, 653356, 650868, 651417, 653366, 649601, 649696, 650410, 653443, 653528, 651068, 0, 650436, 653346, 650450, 653288

-

4.1.1.28

Tryptophan = Tryptamine + CO2

0

-

4.1.1.28

3 entries

4.1.1.53

Tryptophan = Tryptamine + CO2

0

-

4.3.3.2

3-alpha(S)-strictosidine + H2O = tryptamine + secologanin

0

2fpb, 3D-view

Activator in Enzyme-catalyzed Reactions (2 results)

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Show Activating Compound (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.5

27% increase in pyridoxamine 5-phosphate oxidase activity

391873

-

2.1.1.4

activates by 25%

734546

-

Inhibitor in Enzyme-catalyzed Reactions (44 results)

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Show Inhibitors (44 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.7

-

712714

-

1.11.2.2

-

764283

-

1.13.11.52

-

395452, 657865, 666239

-

1.13.11.52

0.1 mM, 16% inhibition of cleavage of D-tryptophan, 11% inhibition of cleavage of L-tryptophan

663910

-

1.13.11.52

1 mM, 23% inhibition

395455

-

1.13.11.52

3 entries

1.13.12.3

competitive inhibition

439347

-

1.14.14.45

-

741148

-

1.14.14.45

competitive

743440

-

1.14.14.45

Ks value 18 microM

741195

-

1.3.3.10

-

639383

-

1.3.3.10

competitive inhibition, Ki: 0.0054 mMl

639382

-

1.4.3.21

during the oxidation of these suicide substrates, the reversible formation of an enzyme-killer product complex occurs followed by an irreversible inactivation of the enzyme, typical of mechanism-based inactivation

676364

-

1.4.3.21

substrate inhibition

703130

-

1.4.9.2

substrate inhibition

396591

-

1.4.9.2

substrate inhibition at higher concentrations

655062

-

1.14.14.45

3 entries

1.3.3.10

2 entries

1.4.3.21

2 entries

1.4.9.2

2 entries

2.1.1.8

and the hydroxyl derivative

441568

-

2.3.1.107

0.5 mM, 28% inhibition

486108

-

2.3.1.110

0.1 mM inhibits activity with tyramine

486130

-

2.3.1.87

0.01 mM

686212

-

2.3.1.87

above 0.01 mM

673165

-

2.3.1.87

above 1 mM

658812

-

2.3.1.87

inhibitory above 0.03 mM

735981

-

2.7.1.35

-

641409

-

2.7.1.35

no inhibition of activity with pyridoxine, 72% inhibition of activity with pyridoxal

391873

-

2.3.1.87

4 entries

2.7.1.35

2 entries

3.2.1.105

2.5 mM, 15% inhibition of enzyme I and II

135715

-

3.5.1.13

-

208987

-

3.5.1.13

slight inhibition of enzyme form AAA-1 at pH 7.5, no inhibition of enzyme form AAA-2 at pH 5.5

208982

-

3.5.1.13

2 entries

3.5.3.1

-

684384

-

3.5.3.12

-

209398, 209402

-

3.5.3.12

2.5 mM, 50% inhibition

209397

-

3.5.3.12

2 entries

3.7.1.3

competitive inhibition, 10 mM

289258

-

4.1.1.105

competitive inhibitor

746086

-

4.1.1.28

-

4203

-

4.1.1.28

5% inhibition at 1 mM

743978

-

4.1.1.28

competitive inhibitor

653443

-

4.1.1.28

3 entries

4.1.1.53

42% inhibition at 0.1% v/v

4708

-

4.1.3.27

-

33305

-

4.3.3.2

inhibitory above 0.7 mM

393871

2fpb, 3D-view

4.3.3.2

inhibitory above 1 mM, soluble and immobilized enzyme

648716

2fpb, 3D-view

4.3.3.2

inhibitory above 1.2 mM

648713

2fpb, 3D-view

6.1.1.2

-

299

-

6.1.1.2

a metabolic tryptophan analog that acts as a potent competitive inhibitor of TrpRS, overview

676170

-

6.1.1.2

competitive, inhibition of the enzyme leads to inhibition of protein biosynthesis, tryptamine stabilizes the enzyme

650759

-

4.3.3.2

3 entries

6.1.1.2

3 entries

6.3.2.18

1 mM completely inhibits synthesis of Nalpha-gamma-L-glutamylhistamine

1102

-

3D Structure of Enzyme-Ligand-Complex (PDB) (12 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (12 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.14.19.9

7ju0, 3D-view

1.4.99.4

2agw, 3D-view

1.4.99.4

2iuq, 3D-view

1.4.99.4

2agw, 3D-view

1.4.99.4

2iuq, 3D-view

3.4.21.4

3atm, 3D-view

3.4.21.4

3rxi, 3D-view

3.4.21.4

7wba, 3D-view

3.4.21.4

3atm, 3D-view

3.4.21.4

3rxi, 3D-view

3.4.21.4

7wba, 3D-view

1.4.99.4

4 entries

3.4.21.4

6 entries

4.3.3.2

2fpb, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (23 results)

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Show Turnover Number (23 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.13.11.52

0.00483

-

24°C

395462

1.4.3.21

2.7

-

-

676364

1.4.3.22

100

-

-

391951

1.4.3.4

0.066

-

30°C, mutant enzyme Y402A

394556

1.4.3.4

0.183

-

30°C, mutant enzyme Y407A

394556

1.4.3.4

1.2

-

30°C, mutant enzyme Y410A

394556

1.4.3.4

1.8

-

30°C, mutant enzyme Y402F

394556

1.4.3.4

2.4

-

30°C, mutant enzyme Y407F

394556

1.4.3.4

3.5

-

30°C, wild-type enzyme

394556

2.1.1.49

0.4

-

transferase A, pH 8.5

441354

2.1.1.49

0.45

-

transferase B, pH 8.5

441354

2.3.1.87

3

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

3.05

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

7.345

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

16

-

wild-type, pH 8.0, 22°C

735681

4.3.3.2

0.002

-

-

694743

4.3.3.2

0.015

-

HPLC, neutral pH, micromolar to low millimolar substrate concentrations

664326

4.3.3.2

0.057

0.65

wild-type enzyme

679176

4.3.3.2

0.64

-

mutant V208A

679176

4.3.3.2

1.3

-

wild-type strictosidine synthase expressed in yeast

679175

4.3.3.2

10.65

-

wild-type enzyme

679176, 694743

4.3.3.2

11.31

-

mutant V208A

694743

4.3.3.2

54.09

-

mutant V208A

679176

1.4.3.4

6 entries

2.1.1.49

2 entries

2.3.1.87

4 entries

4.3.3.2

8 entries

K_M Value (90 results)

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Show KM Value (90 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.52

0.075

-

24°C

395462

1.4.3.21

0.5

-

-

676364

1.4.3.22

0.1

-

-

391951

1.4.3.4

0.0185

-

-

394562

1.4.3.4

0.028

-

30°C, mutant enzyme Y407F

394556

1.4.3.4

0.033

-

30°C, wild-type enzyme

394556

1.4.3.4

0.035

-

30°C, mutant enzyme Y402F

394556

1.4.3.4

0.038

-

30°C, mutant enzyme Y410A

394556

1.4.3.4

0.055

-

30°C, mutant enzyme Y402A

394556

1.4.3.4

0.066

-

-

394560

1.4.3.4

3

-

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

725620

1.4.3.4

3.1

-

30°C, mutant enzyme Y407A

394556

1.4.3.4

4.53

-

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

711832

1.4.3.4

4.9

-

at pH 7.4 and 25°C

742989

1.4.3.4

5.1

-

at pH 7.4 and 25°C

742990

1.4.3.4

12 entries

1.4.9.2

0.0092

-

-

396591

1.5.3.16

2.5

-

pH 8.5, 37°C

690790

1.5.3.17

2.5

-

pH 8.5, 37°C

690790

2.1.1.49

0.12

-

transferase B, pH 8.5

441354

2.1.1.49

0.3

-

transferase A, pH 8.5

441354

2.1.1.49

8.3

-

5-methyltetrahydrofolate as methyl donor

441353

2.1.1.49

28.3

-

mitochondrial enzyme, cholestatic liver, S-adenosyl-L-methionine

441356

2.1.1.49

32.5

-

mitochondrial enzyme, control liver, S-adenosyl-L-methionine

441356

2.1.1.49

34.1

-

microsomal enzyme, cholestatic liver, S-adenosyl-L-methionine

441356

2.1.1.49

35.6

-

microsomal enzyme, control liver, S-adenosyl-L-methionine

441356

2.3.1.110

0.059

-

with feruloyl-CoA as acceptor

486130

2.3.1.110

0.848

-

pH 8.5, 30°C

660244

2.3.1.110

24

-

30°C, pH 8.5, recombinant enzyme

676598

2.3.1.5

0.031

-

-

487105

2.3.1.5

0.24

0.25

-

487122

2.3.1.5

0.24

0.25

liver

487123

2.3.1.5

0.53

-

pineal gland

487116

2.3.1.87

0.0017

-

-

673165

2.3.1.87

0.002

-

-

487634

2.3.1.87

0.00331

-

pH 7.4, 37°C

735981

2.3.1.87

0.026

-

wild-type, pH 8.0, 22°C

735681

2.3.1.87

0.0315

-

-

487105

2.3.1.87

0.1

-

-

658812

2.3.1.87

0.1

-

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

756913

2.3.1.87

0.11

-

-

487644

2.3.1.87

0.12

-

-

672840

2.3.1.87

0.14

-

-

672840

2.3.1.87

0.16

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

0.17

-

pH 6.8, 30°C, phosphorylated T31, unphosphorylated S205

660381

2.3.1.87

0.17

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

0.18

-

pH 6.8, 30°C, unphosphorylated enzyme

660381

2.3.1.87

0.24

-

liver

487123

2.3.1.87

0.25

-

pH 6.8, 30°C, mutant enzyme S205A, phosphorylated T31

660381

2.3.1.87

0.28

-

pH 6.8, 30°C, mutant enzyme S205A, unphosphorylated

660381

2.3.1.87

0.291

-

pH 6.8, 37°C, mutant enzyme S192V

659760

2.3.1.87

0.3

-

pH 6.8, 30°C, mutant enzyme T31A, phosphorylated S205

660381

2.3.1.87

0.31

-

pH 6.8, 30°C, mutant enzyme T31A, unphosphorylated

660381

2.3.1.87

0.317

-

pH 6.8, 37°C, mutant enzyme T29V/S203G

659760

2.3.1.87

0.33

-

pH 6.8, 37°C, recombinant wild-type enzyme

704421

2.3.1.87

0.344

-

pH 6.8, 37°C, mutant enzyme T127V

659760

2.3.1.87

0.361

-

pH 6.8, 37°C, wild-type enzyme

659760

2.3.1.87

0.413

-

pH 6.8, 37°C, mutant enzyme T29V

659760

2.3.1.87

0.417

-

pH 6.8, 37°C, mutant enzyme S203G

659760

2.3.1.87

0.53

-

pineal gland

487123

2.3.1.87

0.6

-

-

487629

2.3.1.87

0.91

-

-

487644

2.3.1.87

1.4

-

pH 6.8, 27°C

658812

2.3.1.87

2.3

-

pH 6.8, 37°C, recombinant mutant I57A/V59A

704421

2.3.1.87

4

-

above, pH 6.8, 37°C, recombinant mutants P64A, P64G, P64W, and recombinant truncation mutants

704421

2.3.1.87

4.3

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

4.3.3.2

0.0014

-

wild-type strictosidine synthase expressed in yeast

679175

4.3.3.2

0.002

-

isoform I b

648723

4.3.3.2

0.003

-

isoform II b

648723

4.3.3.2

0.0054

-

E309A, pH 7.0, 35°C, 15 min

666582

4.3.3.2

0.0062

-

wild type, pH 7.0, 35°C, 15 min

666582

4.3.3.2

0.007

-

-

694743

4.3.3.2

0.0074

-

HPLC, neutral pH, micromolar to low millimolar substrate concentrations

664326

4.3.3.2

0.0079

-

H307A, pH 7.0, 35°C, 15 min

666582

4.3.3.2

0.008

-

isoform I a

648723

4.3.3.2

0.009

-

pH 6.8, 30°C

648725

4.3.3.2

0.015

-

isoform II a

648723

4.3.3.2

0.0172

-

Y151F, pH 7.0, 35°C, 15 min

666582

4.3.3.2

0.072

-

wild-type enzyme

679176, 694743

4.3.3.2

0.219

-

mutant V208A

679176, 694743

4.3.3.2

0.42

-

mutant V214M

679175

4.3.3.2

0.44

-

mutant E315A

679175

4.3.3.2

0.5

-

hairy root enzyme, 37°C

648730

4.3.3.2

0.62

-

mutant F232L

679175

4.3.3.2

0.83

-

pH 7.5, 30°C

648714

4.3.3.2

0.9

-

immobilized enzyme, pH 6.5, 37°C

648716

4.3.3.2

1

-

-

393871

4.3.3.2

2.3

-

pH 7.0, 35°C

648713

4.3.3.2

2.3

-

soluble enzyme, pH 6.5, 37°C

648716

4.3.3.2

4

-

-

648719

4.3.3.2

5.8

-

pH 7.0, 35°C

648715

2.1.1.49

7 entries

2.3.1.110

3 entries

2.3.1.5

4 entries

2.3.1.87

33 entries

4.3.3.2

25 entries

K_i Value (8 results)

top print hide

Show KI Value (8 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.13.11.52

0.1

-

-

395452

1.13.11.52

0.255

-

-

657865

1.13.11.52

1.8

-

-

395452

1.13.11.52

3 entries

1.3.3.10

0.0054

-

-

639382, 639383

1.4.3.21

0.032

-

recombinant enzyme expressed in CHO cells

703130

3.5.3.12

2.5

-

-

209397

4.1.1.105

0.31

-

at pH 7.5, temperature not specified in the publication

746086

4.1.1.28

0.31

-

-

653443

IC₅₀ Value (2 results)

top print hide

Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.5.3.1

3.2

-

in the presence of 0.5 mM MnCl2, at 37°C

684384

3.5.3.1

3.4

-

in the presence of 0.5 mM MnCl2, at 37°C

684384

3.5.3.1

2 entries

References & Links

Literature References (179)

top print hide

Show Reference (179 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

299

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Tryptophanyl-tRNA synthetase from beef pancreas

1979

Kisselev, L.L.; Favorova, O.O.; Kovaleva, G.K.

Methods Enzymol.

54

234-257

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

4202

4441405

Constitutive aromatic L-amino acid decarboxylase from Micrococcus percitreus

1974

Nakazawa, H.; Kumagai, H.; Yamada, H.

Biochem. Biophys. Res. Commun.

61

75-82

4203

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Partial purification and some properties of tryptophan decarboxylase from Phalaris tuberosa

1972

Baxter, C.; Slaytor, M.

Phytochemistry

11

2763-2766

4708

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Distribution and formation of aromatic L-amino acid decarboxylase in bacteria

1977

Nakazawa, H.; Sano, K.; Kumagai, H.; Yamada, H.

Agric. Biol. Chem.

41

2241-2247

33305

8444181

Purification and characterization of anthranilate synthase from Catharanthus roseus

1993

Poulsen, C.; Bongaerts, R.J.M.; Verpoorte, R.

Eur. J. Biochem.

212

431-440

135715

6768587

Glucosidases involved in indole alkaloid biosynthesis of Catharanthus cell culture

1980

Hemscheid, T.; Zenk, M.H.

FEBS Lett.

110

187-191

208982

15714771

Rat brain aryl acylamidase: multiple forms and inhibition effects of LSD, serotonin and related compounds

1977

Hsu, L.L.; Paul, S.M.; Halaris, A.E.; Freedman, D.X.

Life Sci.

20

857-866

208987

4447669

Serotonin-sensitive aryl acylamidase in rat brain

1974

Fujimoto, D.

Biochem. Biophys. Res. Commun.

61

72-74

209397

-

Purification and properties of agmatine iminohydrolase from groundnut cotyledons

1979

Sindhu, R.K.; Desai, H.V.

Phytochemistry

18

1937-1938

209398

16661738

Corn agmatine iminohydrolase. Purification and properties

1981

Yanagisawa, H.; Suzuki, Y.

Plant Physiol.

67

697-700

209402

-

Agmatine deiminase in rice seedlings

1985

Chaudhuri, M.M.; Ghosh, B.

Phytochemistry

24

2433-2435

289258

13129249

Kynureninase from Neurospora: Interaction of enzyme with substrates, coenzyme, and amines

1953

Jacoby, W.B.; Bonner, D.M.

J. Biol. Chem.

205

709-715

391873

2988502

Effect of tryptophan metabolites on the activities of rat liver pyridoxal kinase and pyridoxamine 5-phosphate oxidase in vitro

1985

Takeuchi, F.; Tsubouchi, R.; Shibata, Y.

Biochem. J.

227

537-544

391879

7181092

A radiometric assay of pyridoxamine (pyridoxine) 5-phosphate oxidase

1982

Langham, L.; Garber, B.M.; Roe, D.A.; Kazarinoff, M.N.

Anal. Biochem.

125

329-334

391941

-

Purification and properties of the diamine oxidase from Vicia faba leaves

1981

Matsuda, H.; Suzuki, Y.

Plant Cell Physiol.

22

737-746

391951

7727530

Amine oxidases from Aspergillus niger: identification of a novel flavin-dependent enzyme

1995

Schilling, B.; Lerch, K.

Biochim. Biophys. Acta

1243

529-537

393871

7764480

Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture

1994

Kutchan, T.M.; Bock, A.; Dittrich, H.

Phytochemistry

35

353-360

394548

6061707

Mitochondrial monoamine oxidase. I. Purification and characterization of the bovine kidney enzyme

1967

Erwin, V.G.; Hellerman, L.

J. Biol. Chem.

242

4230-4238

394556

11754741

Tyrosine residues near the FAD binding site are critical for FAD binding and for the maintenance of the stable and active conformation of rat monoamine oxidase A

2002

Ma, J.; Ito, A.

J. Biochem.

131

107-111

394557

5165518

Purification and properties of pig liver mitochondrial monoamine oxidase

1971

Oreland, L.

Arch. Biochem. Biophys.

146

410-412

394560

4357526

Rapid screening assay for revertants derived from MSV-transformed cells

1973

Tipton, M.F.; Houslay, M.D.; Garrett, N.J.

Nature

246

213-214

394562

4850215

A kinetic evaluation of monoamine oxidase activity in rat liver mitochondrial outer membranes

1974

Houslay, M.D.; Tipton, K.F.

Biochem. J.

139

645-652

394580

434814

Monoamine oxidase from beef liver mitochondria: simplified isolation procedure, properties, and determination of its cysteinyl flavin content

1979

Salach, J.I.

Arch. Biochem. Biophys.

192

128-137

395452

-

Heme-containing dioxygenases

1974

Feigelson, P.; Brady, F.O.

Mol. Mech. Oxygen Activ. (Hayaishi, O., ed.) Academic Press, New York

-

87-133

395455

6712960

L-Tryptophan 2,3-dioxygenase of a moderate thermophile, Bacillus brevis. Purification, properties and a substrate-mediated stabilization of the quaternary structure

1984

Matsumura, M.; Osada, K.; Aiba, S.

Biochim. Biophys. Acta

786

9-17

395459

3298973

Indoleamine 2,3-dioxygenase

1987

Yoshida, R.; Hayaishi, O.

Methods Enzymol.

142

188-195

395462

26687

Indoleamine 2,3-dioxygenase. Purification and some properties

1978

Shimizu, T.; Nomiyama, S.; Hirata, F.; Hayaishi, O.

J. Biol. Chem.

253

4700-4706

395472

10564724

Human placental indoleamine 2,3-dioxygenase: cellular localization and characterization of an enzyme preventing fetal rejection

2000

Kudo, Y.; Boyd, C.A.R.

Biochim. Biophys. Acta

1500

119-124

396589

3037269

Aromatic amine dehydrogenase from Alcaligenes faecalis

1987

Nozaki, M.

Methods Enzymol.

142

650-655

396591

6830237

Crystallization and properties of aromatic amine dehydrogenase from Pseudomonas sp

1983

Iwaki, M.; Yagi, T.; Horiike, K.; Saeki, Y.; Ushijima, T.; Nozaki, M.

Arch. Biochem. Biophys.

220

253-262

439304

3037258

Purification and properties of tryptophan side chain oxidase types I and II from Pseudomonas

1987

Takai, K.; Hayaishi, O.

Methods Enzymol.

142

195-217

439307

-

cristalline hemoprotein from Pseudomonas that catalyzes oxidation of side chain of tryptophan and other indole derivatives

1977

Takai, K.; Ushiro, H.; Noda, Y.; Narumiya, S.; Tokuyama, T.; Hayaishi, O.

J. Biol. Chem.

252

2638-2656

439347

7840624

Purification and characterization of the flavoprotein tryptophan 2-monooxygenase expressed at high levels in Escherichia coli

1995

Emanuele, J.J.; Heasley, C.J.; Fitzpatrick, P.F.

Arch. Biochem. Biophys.

316

241-248

441352

3707620

Reevaluation of the products of tryptamine catalyzed by rabbit liver N-methyltransferases

1986

Crooks, P.A.; Godin, C.S.; Nwosu, C.G.; Ansher, S.S.; Jakoby, W.B.

Biochem. Pharmacol.

35

1600-1603

441353

4766261

Multiple N-methyltransferases for aromatic alkylamines in brain

1973

Hsu, L.L.; Mandell, A.J.

Life Sci.

13

847-858

441354

3949799

Amine N-methyltransferases from rabbit liver

1986

Ansher, S.S.; Jakoby, W.B.

J. Biol. Chem.

261

3996-4001

441356

11322482

Arylamine N-methyltransferase and thiol methyltransferase activities in cholestatic rat liver induced by common bile duct ligation

2001

Kim, Y.H.; Joo, I.

Exp. Mol. Med.

33

23-28

441568

3952132

Inhibition of rat kidney histamine-N-methyltransferase by biogenic amines

1986

Fuhr, N.; Kownatzki, E.

Pharmacology

32

114-120

486108

2350183

Purification and characterization of acetylcoenzyme A: deacetylvindoline 4-O-acetyltransferase from Catharanthus roseus

1990

Power, R.; Kurz, W.G.W.; de Luca, V.

Arch. Biochem. Biophys.

279

370-376

486130

10879473

Induction of N-hydroxycinnamoyltyramine synthesis and tyramine N-hydroxycinnamoyltransferase (THT) activity by wounding in maize leaves

2000

Ishihara, A.; Kawata, N.; Matsukawa, T.; Iwamura, H.

Biosci. Biotechnol. Biochem.

64

1025-1031

487105

1453312

Determination of kinetic properties of serotonin-N-acetyltransferase in bovine pineal gland using HPLC with fluorimetric detection

1992

Fajardo, N.; Abreu, P.; Alonso, R.

J. Pineal Res.

13

80-84

487116

-

Amine:acetyl CoenzymeA acetyltransferase from the soluble fraction of Hansenula ciferri: isolation and properties

1974

Barenholz, Y.; Edelman, I.; Gatt, S.

Biochim. Biophys. Acta

358

262-274

487120

44212

N-Acylation of tyramines: purification and characterization of an arylamine N-acetyltransferase from rat brain and liver

1979

Yu, P.H.; Boulton, A.A.

Can. J. Biochem.

57

1204-1209

487122

2294966

Assay for acetyl-CoA:arylamine N-acetyltransferase by high-performance liquid chromatography applied to serotonin N-acetylation

1990

Mannens, G.; Siegers, G.; Claeys, A.

Biochim. Biophys. Acta

1037

1-6

487123

883970

Comparison of rat pineal gland and rat liver serotonin-N-acetyltransferase

1977

Morrissey, J.J.; Edwards, S.B.; Lovenberg, W.

Biochem. Biophys. Res. Commun.

77

118-123

487126

2583181

Two arylamine N-acetyltransferases from chicken pineal gland as identified by cDNA cloning

1989

Ohtomi, M.; Sasaki, M.; Deguchi, T.

Eur. J. Biochem.

185

253-261

487621

3298986

Arylalkylamine N-acetyltransferase from mammalian pineal gland

1987

Namboodiri, M.A.A.; Dubbels, R.; Klein, D.C.

Methods Enzymol.

142

583-590

487622

6469990

Arylamine N-acetyltransferase and arylalkylamine N-acetyltransferase in the mammalian pineal gland

1984

Voisin, P.; Namboodiri, M.A.A.; Klein, D.C.

J. Biol. Chem.

259

10913-10918

487623

-

Characteristics of the enzyme N-acetyltransferase in the optic lobe of the giant freshwater prawn, Macrobrrachium rosenbergii

1993

Withyachumnarnkul, B.; Pongsa-Asawapaiboon, A.; Poolsanguan, B.

Comp. Biochem. Physiol. B

104

449-454

487628

3625455

Multiple forms of arylalkylamine N-acetyltransferases in the rat pineal gland: purification of one molecular form

1987

Namboodiri, M.A.A.; Brownstein, M.J.; Weller, J.L.; Voisin, P.; Klein, D.C.

J. Pineal Res.

4

235-246

487629

167124

Characteristics of serotonin-acetyl coenzyme A N-acetyltransferase in pineal gland of rat

1975

Deguchi, T.

J. Neurochem.

24

1083-1085

487631

9927331

Ovine arylalkylamine N-acetyltransferase in the pineal and pituitary glands: differences in function and regulation

1999

Fleming, J.V.; Barrett, P.; Coon, S.L.; Klein, D.C.; Morgan, P.J.

Endocrinology

140

972-978

487632

11316744

Regulation of arylalkylamine N-acetyltransferase-2 (AANAT2, EC 2.3.1.87) in the fish pineal organ: evidence for a role of proteasomal proteolysis

2001

Falcon, J.; Galarneau, K.M.; Weller, J.L.; Ron, B.; Chen, G.; Coon, S.L.; Klein, D.C.

Endocrinology

142

1804-1813

487634

8740555

Characterization of the arylalkylamine N-acetyltransferase in Onchocerca volvulus

1996

Aisien, S.O.; Hellmund, C.; Walter, R.D.

Parasitol. Res.

82

369-371

487637

11098219

Purification, cloning, and characterization of a second arylalkylamine N-acetyltransferase from Drosophila melanogaster

2000

Amherd, R.; Hintermann, E.; Walz, D.; Affolter, M.; Meyer, U.A.

DNA Cell Biol.

19

697-705

487644

10722724

Substrate specificity and inhibition studies of human serotonin N-acetyltransferase

2000

Ferry, G.; Loynel, A.; Kucharczyk, N.; Bertin, S.; Rodriguez, M.; Delagrange, P.; Galizzi, J.P.; Jacoby, E.; Volland, J.P.; Lesieur, D.; Renard, P.; Canet, E.; Fauchere, J.L.; Boutin, J.A.

J. Biol. Chem.

275

8794-8805

487646

9090119

Purification and characterization of arylalkylamine N-acetyltransferase from cockroach testicular organs

1997

Ichihara, N.; Okada, M.; Nakagawa, H.; Takeda, M.

Insect Biochem. Mol. Biol.

27

241-246

639382

7559518

L-tryptophan 2',3'-oxidase from Chromobacterium violaceum

1995

Genet, R.; Benetti, P.H.; Hammadi, A.; Menez, A.

J. Biol. Chem.

270

23540-23545

639383

8027079

Purification and partial characterization of an amino acid alpha,beta-dehydrogenase, L-tryptophan 2',3'-oxidase from Chromobacterium violaceum

1994

Genet, R.; Donoyelle, C.; Menez, A.

J. Biol. Chem.

269

18177-18184

641409

4356198

Inhibition of pyridoxal kinase from rat liver in vitro by aromatic and aliphatic amines

1973

Gaeng, V.; von Collins, E.N.

Int. J. Vitam. Nutr. Res.

43

318-323

648713

510306

Purification and properties of strictosidine synthase, the key enzyme in indole alkaloid formation

1979

Treimer, J.F.; Zenk, M.H.

Eur. J. Biochem.

101

225-233

648714

476085

Purification and properties of strictosidine synthetase (an enzyme condensing tryptamine and secologanin) from Catharanthus roseus cultured cell

1979

Mizukami, H.; Nordlov, H.; Lee, S.L.; Scott, A.I.

Biochemistry

18

3760-3763

648715

-

Strictosidine synthase from cell cultrues of Apocynaceae plants

1979

Treimer, J.F.; Zenk, M.H.

FEBS Lett.

97

159-162

648716

17396930

Immobilization of strictosidine synthase from Catharanthus cell cultures and preparative synthesis of strictosidine

1982

Pfitzner, U.; Zenk, M.H.

Planta Med.

46

10-14

648717

-

Tryptophan decarboxylase, strictosidine synthase and alkaloid production by Cinchona ledgerinana suspension cultures

1987

Skinner, S.E.; Walton, N.J.; Robins, R.J.; Rhodes, M.J.C.

Phytochemistry

26

721-725

648718

-

Isoation and immobilization of strictosidine synthase

1987

Pfitzner, U.; Zenk, M.H.

Methods Enzymol.

136

342-350

648719

-

Homogeneous strictosidine synthase from cell suspension cultures of Rauvolfia serpentina

1988

Hampp, N.; Zenk, M.H.

Phytochemistry

27

3811-3815

648720

2742131

Assay of trictosidine synthase from plant cell cultures by high-performance liquid chromatography

1989

Pennings, E.J.M.; Van den Bosch, R.A.; Van der Heijden, R.; Stevens, L.H.; Duine, J.A.; Verpoorte, R.

Anal. Biochem.

176

412-415

648721

1330135

Purification of an indole alkaloid biosynthetic enzyme, strictosidine synthase, from a recombinant strain of Escherichia coli

1992

Roessner, C.A.; Devagupta, R.; Hasan, M.; Williams, H.J.; Scott, A.I.

Protein Expr. Purif.

3

295-300

648722

1567228

Strictosidine synthase from Rauvolfia serpentina: analysis of a gene involved in indole alkaloid biosynthesis

1992

Bracher, D.; Kutchan, T.M.

Arch. Biochem. Biophys.

294

717-723

648723

-

Purification and characterization of strictosidine synthase from a suspension culture of Cinchona robusta

1993

Stevens, L.H.; Giroud, C.; Pennings, E.J.M.; Verpoorte, R.

Phytochemistry

33

99-106

648725

7887913

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