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Ligand octopamine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.1.87

octopamine = (4-hydroxyphenyl)acetaldehyde + NH3 + H2O

288289

-

Substrate in Enzyme-catalyzed Reactions (16 results)

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Show Substrate (16 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.9

octopamine + FMNH + O2 = norepinephrine + FMN + H2O

744169

-

1.14.17.1

octopamine + ascorbate + O2 = ?

438610, 438620

-

1.4.3.21

octopamine + H2O + O2 = hydroxy(hydroxyphenyl)acetaldehyde + NH3 + H2O2

725733

-

1.4.3.22

octopamine + H2O + O2 = ?

391951

-

2.1.1.28

DL-octopamine + S-adenosyl-L-methionine = ? + S-adenosyl-L-homocysteine

639430

-

2.1.1.28

octopamine + S-adenosyl-L-methionine = N-methyloctopamine + S-adenosyl-L-homocysteine

672011, 733211

-

2.3.1.110

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

486133

-

2.3.1.110

feruloyl-CoA + octopamine = CoA + feruloyloctopamine

486133, 486126, 486132, 486128

-

2.1.1.28

2 entries

2.3.1.110

2 entries

2.3.1.5

acetyl-CoA + p-octopamine = CoA + N-acetyloctopamine

487120, 487628

-

2.3.1.87

acetyl-CoA + octopamine = CoA + N-acetyloctopamine

735681, 686212, 719595, 758432, 487634, 487646, 673165, 735981, 756913

-

2.3.1.87

arachidonoyl-CoA + octopamine = CoA + N-arachidonoyloctopamine

736107

-

2.3.1.87

oleoyl-CoA + octopamine = CoA + N-oleoyloctopamine

736107

-

2.3.1.87

palmitoyl-CoA + octopamine = CoA + N-palmitoyloctopamine

736107

-

2.3.1.87

stearoyl-CoA + octopamine = CoA + N-stearoyloctopamine

736107

-

2.3.1.87

5 entries

4.2.1.87

octopamine = (4-hydroxyphenyl)acetaldehyde + NH3 + H2O

288289

-

4.2.1.88

(+/-)-octopamine = (4-hydroxyphenyl)acetaldehyde + NH3 + H2O

648464

-

Product in Enzyme-catalyzed Reactions (10 results)

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Show Product (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.17.1

beta,beta-dideuterated tyramine + ascorbate + O2 = octopamine + dehydroascorbate + H2O

0

-

1.14.17.1

tyramine + ascorbate + ferrocyanide = octopamine + dehydroascorbate + ?

0

-

1.14.17.1

tyramine + ascorbate + N,N,N',N'-tetramethyl-p-phenylenediamine = octopamine + dehydroascorbate + ?

0

-

1.14.17.1

tyramine + ascorbate + N,N-dimethyl-p-phenylenediamine = octopamine + dehydroascorbate + ?

0

-

1.14.17.1

tyramine + ascorbate + O2 = octopamine + dehydroascorbate + H2O

0, 438631, 438632, 438621, 438629

-

1.14.17.1

tyramine + N-(4-chlorophenyl)-N'-hydroxyguanidine + O2 = octopamine + 1-(4-chlorophenyl)urea + (4-chlorophenyl)cyanamide + 1-oxo-2-(4-chlorophenyl)guanidine + H2O

0

-

1.14.17.1

tyramine + N-(4-isopropylphenyl)-N'-hydroxyguanidine + O2 = octopamine + 1-(4-isopropylphenyl)urea + (4-isopropylphenyl)cyanamide + 1-oxo-2-(4-isopropylphenyl)guanidine + H2O

0

-

1.14.17.1

tyramine + N-(4-methoxyphenyl)-N'-hydroxyguanidine + O2 = octopamine + 1-(4-methoxyphenyl)urea + (4-methoxyphenyl)cyanamide + 1-oxo-2-(4-methoxyphenyl)guanidine + H2O

0

-

1.14.17.1

tyramine + N-(4-methylphenyl)-N'-hydroxyguanidine + O2 = octopamine + 1-(4-methylphenyl)urea + (4-methylphenyl)cyanamide + 1-oxo-2-(4-methylphenyl)guanidine + H2O

0

-

1.14.17.1

tyramine + N-(4-trifluoromethylphenyl)-N'-hydroxyguanidine + O2 = octopamine + 1-(4-trifluoromethylphenyl)urea + (4-trifluoromethylphenyl)cyanamide + 1-oxo-2-(4-trifluoromethylphenyl)guanidine + H2O

0

-

1.14.17.1

10 entries

Activator in Enzyme-catalyzed Reactions (3 results)

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Show Activating Compound (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.99.22

-

699193

-

3.1.1.59

10 mM, activates JHE activity of newly ecdysed pupae

651397

-

3.1.1.59

exogenous octopamine, 0.1 -10 mM, stimulates JHE activity of final instars at day 2

651397

-

3.1.1.59

2 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.4.3.21

-

725733

-

1.5.1.34

0.19 mM, 50% inhibition

484984

-

2.1.1.28

at high concentrations

639433

-

3.1.6.1

-

135516, 135519

-

6.3.2.18

effective inhibitor, 1 mM inhibits Nalpha-gamma-L-glutamylhistamine synthesis by 91%

1102

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (11 results)

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Show Turnover Number (11 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.17.1

33

-

-

438610

1.4.3.21

3.5

-

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

725733

1.4.3.22

122

-

-

391951

2.1.1.28

0.02

-

wild type enzyme, assay mixture consists of 25 microl of 0.5 M phosphate buffer (pH 8.0), 5 microl of [methyl-3H]S-adenosyl-L-methionine containing approximately 2.5 X 10 00000 dpm, varying amounts of phenylethanolamine and unlabeled S-adenosyl-L-methionine, 20 microl enzyme and water at 30°C.

672011

2.1.1.28

0.021

-

pH 8.0, 30°C

733211

2.3.1.87

1.8

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

2.56

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

3.1

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

4

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

7.26

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

16

-

wild-type, pH 8.0, 22°C

735681

2.1.1.28

2 entries

2.3.1.87

6 entries

K_M Value (15 results)

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Show KM Value (15 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.17.1

14

-

-

438610

1.4.3.21

0.03

-

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

725733

1.4.3.22

0.36

-

-

391951

2.1.1.28

0.0055

-

pH 8.0, 30°C

733211

2.1.1.28

0.0055

-

wild type enzyme, assay mixture consists of 25 microl of 0.5 M phosphate buffer (pH 8.0), 5 microl of [methyl-3H]S-adenosyl-L-methionine containing approximately 2.5 X 10 00000 dpm, varying amounts of phenylethanolamine and unlabeled S-adenosyl-L-methionine, 20 microl enzyme and water at 30°C.

672011

2.1.1.28

2 entries

2.3.1.110

0.0113

-

-

486132

2.3.1.5

1.3

-

liver

487120

2.3.1.87

0.002

-

-

487634

2.3.1.87

0.07

-

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

756913

2.3.1.87

0.12

-

wild-type, pH 8.0, 22°C

735681

2.3.1.87

0.13

-

pH 7.3, 22°C, recombinant aaNAT2

719595

2.3.1.87

0.14

-

pH 7.3, 22°C, recombinant aaNAT1

719595

2.3.1.87

0.94

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

6.2

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

30

-

cosubstrate acetyl-CoA, pH 7.0, 25°C

758432

2.3.1.87

8 entries

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.4.3.21

0.6

-

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

725733

References & Links

Literature References (37)

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Show Reference (37 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

135516

-

Purification and properties of arylsulfatase of Klebsiella aerogenes. Identity of the enzymes formed by non-repressed and de-repressed synthesis

1976

Okamura, H.; Yamada, T.; Murooka, Y.; Harada, T.

Agric. Biol. Chem.

40

2071-2076

135519

16345546

Formation and purification of Serratia marcescens arylsulfatase

1980

Murooka, Y.; Yim, M.H.; Harada, T.

Appl. Environ. Microbiol.

39

812-817

288289

3034855

Initial catabolism of aromatic biogenic amines by Pseudomonas aeruginosa PAO: pathway description, mapping of mutations, and cloning of essential genes

1987

Cuskey, S.M.; Peccoraro, V.; Olsen, R.H.

J. Bacteriol.

169

2398-2404

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

438610

6860408

Dopamine-beta-hydroxylase: suicide inhibition by the novel olefinic substrate, 1-phenyl-1-aminomethylethene

1983

May, S.W.; Mueller, P.W.; Padgette, S.R.; Herman, H.H.; Phillips, R.S.

Biochem. Biophys. Res. Commun.

110

161-168

438620

7059582

Dopamine beta-hydroxylase: activity and inhibition in the presence of beta-substituted phenethylamines

1982

Klinman, J.P.; Krueger, M.

Biochemistry

21

67-75

438621

8920906

Mechanism-based inactivation of dopamine beta-monooxygenase in adrenal chromaffin cells

1996

May, S.W.; Young, F.K.; Powers, J.L.; Gill-Woznichak, M.M.

Biochem. Biophys. Res. Commun.

228

278-284

438629

8889820

Selective cleavage and modification of the intersubunit disulfide bonds of bovine dopamine beta-monooxygenase: conversion of tetramer to active dimer

1996

Ishida, T.; Narita, M.; Nozaki, M.; Horiike, K.

J. Biochem.

120

346-352

438631

8027511

Effects of disulfiram on serum dopamine-beta-hydroxylase and blood carbon disulphide concentrations in alcoholics

1994

Caroldi, S.; De Paris, P.; Zotti, S.; Zanella, I.; Brugnone, F.

J. Appl. Toxicol.

14

77-80

438632

7546340

In vitro effect of dithiocarbamate pesticides and of CaNa2EDTA on human serum dopamine-beta-hydroxylase

1995

De Paris, P.; Caroldi, S.

Biomed. Environ. Sci.

8

114-121

484984

6824696

Inhibition of dihydropteridine reductase by catecholamines and related compounds

1983

Shen, R.S.

Biochim. Biophys. Acta

743

129-135

486126

-

The biosynthesis of feruloyltyramine in Nicotiana tabacum

1984

Negrel, J.; Martin, C.

Phytochemistry

23

2797-2801

486128

11382813

Cloning and characterization of a hydroxycinnamoyl-CoA: tyramine N-(hydroxycinnamoyl)transferase induced in response to UV-C and wounding from Capsicum annuum

2001

Back, K.; Jang, S.M.; Lee, B.C.; Schmidt, A.; Strack, D.; Kim, K.M.

Plant Cell Physiol.

42

475-481

486132

9288939

Purification, characterization and partial amino acid sequencing of hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase from tobacco cell-suspension cultures

1997

Negrel, J.; Javelle, F.

Eur. J. Biochem.

247

1127-1135

486133

9933628

Cloning and expression of a potato cDNA encoding hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase

1999

Schmidt, A.; Grimm, R.; Schmidt, J.; Scheel, D.; Strack, D.; Rosahl, S.

J. Biol. Chem.

274

4273-4280

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

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

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

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

639430

13863458

Purification and properties of phenylethanolamine-N-methyltransferase

1962

Axelrod, J.

J. Biol. Chem.

237

1657-1660

639433

4198075

Purification and properties of rat adrenal phenylethanolamine-N-methyl transferase

1973

Pohorecky, L.A.; Baliga, B.S.

Arch. Biochem. Biophys.

156

703-711

648464

3729420

Purification and properties of synephrinase from Arthrobacter synephrinum

1986

Manne, V.; Kutty, K.R.; Pillarisetti, S.R.

Arch. Biochem. Biophys.

248

324-334

651397

10603275

Effect of octopamine on the activity of juvenile-hormone esterase in the silkworm Bombyx mori and the red flour beetle Tribolium freemani

1999

Hirashima, A.; Suetsugu, E.; Hirokado, S.; Kuwano, E.; Taniguchi, E.; Eto, M.

Gen. Comp. Endocrinol.

116

373-381

672011

16363801

Mode of binding of methyl acceptor substrates to the adrenaline-synthesizing enzyme phenylethanolamine N-methyltransferase: implications for catalysis

2005

Gee, C.L.; Tyndall, J.D.; Grunewald, G.L.; Wu, Q.; McLeish, M.J.; Martin, J.L.

Biochemistry

44

16875-16885

673165

17449311

Cloning and characterization of insect arylalkylamine N-acetyltransferase from Bombyx mori

2007

Tsugehara, T.; Iwai, S.; Fujiwara, Y.; Mita, K.; Takeda, M.

Comp. Biochem. Physiol. B Biochem. Mol. Biol.

147

358-366

686212

17449311

Cloning and characterization of insect arylalkylamine N-acetyltransferase from Bombyx mori

2007

Tsugehara, T.; Iwai, S.; Fujiwara, Y.; Mita, K.; Takeda, M.

Comp. Biochem. Physiol. B

147B

358-366

699193

17703313

Role of ecdysone 20-monooxygenase in regulation of 20-hydroxyecdysone levels by juvenile hormone and biogenic amines in Drosophila

2008

Rauschenbach, I.; Gruntenko, N.; Chentsova, N.; Adonyeva, N.; Alekseev, A.

J. Comp. Physiol. B

178

27-32

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

725733

-

Identification, functional expression and kinetic analysis of two primary amine oxidases from Rhodococcus opacus

2012

Foster, A.; Barnes, N.; Speight, R.; Keane, M.

J. Mol. Catal. B

74

73-82

733211

24018397

Kinetic and pH studies on human phenylethanolamine N-methyltransferase

2013

Wu, Q.; McLeish, M.J.

Arch. Biochem. Biophys.

539

1-8

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

735981

23064182

Characterization of arylalkylamine N-acetyltransferase from silkmoth (Antheraea pernyi) and pesticidal drug design based on the baculovirus-expressed enzyme

2013

Tsugehara, T.; Imai, T.; Takeda, M.

Comp. Biochem. Physiol. C

157

93-102

736107

24444601

Identification of an arylalkylamine N-acyltransferase from Drosophila melanogaster that catalyzes the formation of long-chain N-acylserotonins

2014

Dempsey, D.R.; Jeffries, K.A.; Anderson, R.L.; Carpenter, A.M.; Rodriquez Opsina, S.; Merkler, D.J.

FEBS Lett.

588

594-599

744169

28300536

Hydroxylation of 4-hydroxyphenylethylamine derivatives by R263 variants of the oxygenase component of p-hydroxyphenylacetate-3-hydroxylase

2017

Chenprakhon, P.; Dhammaraj, T.; Chantiwas, R.; Chaiyen, P.

Arch. Biochem. Biophys.

620

1-11

756913

27816487

Arylalkylamine N-acetyltransferase 1 gene (TcAANAT1) is required for cuticle morphology and pigmentation of the adult red flour beetle, Tribolium castaneum

2016

Noh, M.Y.; Koo, B.; Kramer, K.J.; Muthukrishnan, S.; Arakane, Y.

Insect Biochem. Mol. Biol.

79

119-129

758432

29402941

Eis, a novel family of arylalkylamine N-acetyltransferase (EC 2.3.1.87)

2018

Pan, Q.; Zhao, F.; Ye, B.

Sci. Rep.

8

2435

Links to other databases for octopamine

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ChEBI

PubChem