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• • Molecular Structure
  • Sum Formula
  • BRENDA Name
  • Synonyms
  • InChIKey
• Roles as Enzyme Ligand
• • In Vivo Substrate
  • In Vivo Product
  • Substrate
  • 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
  • Links

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Ligand 5-methoxytryptamine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

2.1.1.4

S-adenosyl-L-methionine + serotonin = S-adenosyl-L-homocysteine + 5-methoxytryptamine

-

-

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.4

methoxytryptamine + H2O + O2 = ?

675787, 394562

-

2.1.1.49

S-adenosyl-L-methionine + 5-methyloxytryptamine = ?

441354

-

2.3.1.5

acetyl-CoA + 5-methoxytryptamine = CoA + N-acetyl-5-methoxytryptamine

487126, 487130, 487107, 487129

-

2.3.1.87

acetyl-CoA + 5-methoxytryptamine = CoA + N-acetyl-5-methoxytryptamine

487126, 735681, 487644, 487622, 487629

-

2.3.1.87

acetyl-CoA + methoxytryptamine = CoA + N-acetylmethoxytryptamine

719595

-

4.3.3.2

5-methoxytryptamine + secologanin = 10-methoxystrictosidine

648723

-

4.3.3.2

5-methoxy-tryptamine + H2O = ?

679176

-

4.3.3.2

5-methoxytryptamine + secologanin = ? + H2O

716888

-

2.3.1.87

2 entries

4.3.3.2

3 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

2.1.1.4

serotonin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + 5-methoxytryptamine

-

-

2.1.1.4

S-adenosyl-L-methionine + serotonin = S-adenosyl-L-homocysteine + 5-methoxytryptamine

-

-

2.1.1.4

2 entries

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.13

slight

208984

-

6.3.2.18

1 mM inhibits synthesis of Nalpha-gamma-L-glutamylhistamine by 87%

1102

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

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Show Turnover Number (5 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.3.1.87

3.74

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

7.69

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

13.1

-

wild-type, pH 8.0, 22°C

735681

4.3.3.2

0.21

-

mutant V208A

679176

4.3.3.2

79.66

-

mutant V208A

679176

2.3.1.87

3 entries

4.3.3.2

2 entries

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.4.3.4

0.0159

-

-

394562

2.3.1.87

0.042

-

wild-type, pH 8.0, 22°C

735681

2.3.1.87

0.18

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

0.2

-

-

487644

2.3.1.87

0.23

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

4 entries

4.3.3.2

3.592

-

mutant V208A

679176

References & Links

Literature References (17)

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Show Reference (17 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

208984

1275936

Rat brain de-acetylating activity: stereospecific inhibition by LSD and serotonin-related compounds

1976

Paul, S.M.; Halaris, A.E.

Biochem. Biophys. Res. Commun.

70

207-211

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

441354

3949799

Amine N-methyltransferases from rabbit liver

1986

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

J. Biol. Chem.

261

3996-4001

487107

-

Arylamine N-acetyltransferase from the chicken kidney: characterization of the enzyme and localization of the mRNA by in situ hybridization

1990

Ohtomi, M.; Tomoyuki, I.; Deguchi, T.

Biomed. Res.

11

263-267

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

487129

2897359

Arylamine N-acetyltransferase from chicken liver. I. Monoclonal antibodies, immunoaffinity purification, and amino acid sequences

1988

Deguchi, T.; Sakamoto, Y.; Sasaki, Y.; Uyemura, K.

J. Biol. Chem.

263

7528-7533

487130

2897360

Arylamine N-acetyltransferase from chicken liver II. Cloning of cDNA and expression in Chinese hamster ovary cells

1988

Ohsako, S.; Ohtomi, M.; Sakamoto, Y.; Uyemura, K.; Deguchi, T.

J. Biol. Chem.

263

7534-7538

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

487629

167124

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

1975

Deguchi, T.

J. Neurochem.

24

1083-1085

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

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

675787

16979412

Short- and long-term insulin-like effects of monoamine oxidases and semicarbazide-sensitive amine oxidase substrates in cultured adipocytes

2006

Carpene, C.; Daviaud, D.; Boucher, J.; Bour, S.; Visentin, V.; Gres, S.; Duffaut, C.; Fontana, E.; Testar, X.; Saulnier-Blache, J.S.; Valet, P.

Metab. Clin. Exp.

55

1397-1405

679176

17884630

Structure-based engineering of strictosidine synthase: auxiliary for alkaloid libraries

2007

Loris, E.A.; Panjikar, S.; Ruppert, M.; Barleben, L.; Unger, M.; Schuebel, H.; Stoeckigt, J.

Chem. Biol.

14

979-985

716888

-

Biosynthetic system of camptothecin: An anticancer plant product

2010

Yamazaki, M.; Asano, T.; Yamazaki, Y.; Sirikantaramas, S.; Sudo, H.; Saito, K.

Pure Appl. Chem.

82

213-218

719595

21645618

Identification and characterization of two arylalkylamine N-acetyltransferases in the yellow fever mosquito, Aedes aegypti

2011

Mehere, P.; Han, Q.; Christensen, B.M.; Li, J.

Insect Biochem. Mol. Biol.

41

707-714

735681

25406072

Mechanistic and structural analysis of Drosophila melanogaster arylalkylamine N-acetyltransferases

2014

Dempsey, D.R.; Jeffries, K.A.; Bond, J.D.; Carpenter, A.M.; Rodriguez-Ospina, S.; Breydo, L.; Caswell, K.K.; Merkler, D.J.

Biochemistry

53

7777-7793

Links to other databases for 5-methoxytryptamine

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Show Links (1 entry)

ChEBI

PubChem