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• • Molecular Structure
  • Sum Formula
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  • InChIKey
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• 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 2-nitroacetanilide

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

3.5.1.4

2-nitroacetanilide = 2-nitrophenylamine + acetate

209121

-

Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Substrate (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.8

2-nitroacetanilide + H2O = 2-nitroaniline + acetate

678453

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3.5.1.13

2-nitroacetanilide + H2O = 2-nitroacetate + aniline

711318, 711319

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3.5.1.13

2-nitroacetanilide + H2O = 2-nitroaniline + acetate

670800, 754722, 667330, 752591

-

3.5.1.13

N-(2-nitrophenyl)acetamide + H2O = N-(2-nitrophenyl)aniline + acetate

667928

-

3.5.1.13

N-(2-nitrophenyl)acetamide + H2O = N-(2-nitrophenyl)heptananiline + heptanoate

667928

-

3.5.1.13

N-(2-nitrophenyl)acetamide + H2O = N-(2-nitrophenyl)octananiline + octanoate

667928

-

3.5.1.13

o-nitroacetanilide + H2O = 2-nitroaniline + acetate

208977, 208997, 678541, 679287, 208982, 208970, 208979, 208972, 208983, 208996, 208991

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3.5.1.13

o-nitroacetanilide + H2O = 2-nitroaniline + acetic acid

697867, 697902

-

3.5.1.13

o-nitroacetanilide + H2O = o-nitroaniline + acetate

679183

-

3.5.1.13

8 entries

3.5.1.4

2-nitroacetanilide = 2-nitrophenylamine + acetate

209121

-

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.5

acetyl-CoA + 2-nitroaniline = CoA + N-acetyl-2-nitroaniline

-

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.5.1.13

0.05

-

pH 8.0, 23°C, butyrylcholinesterase

667928

3.5.1.13

208

-

-

697902

3.5.1.13

2 entries

3.5.1.4

129

-

-

209121

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.13

0.37

-

strain RA2

208991

3.5.1.13

0.6

-

pH 8.0, 23°C, butyrylcholinesterase

667928

3.5.1.13

1.53

-

strain RA2

208991

3.5.1.13

15.22

-

-

697902

3.5.1.13

4 entries

3.5.1.4

0.042

-

-

209121

References & Links

Literature References (23)

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Show Reference (23 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

208970

6386042

Chemical modification of acetylcholinesterase from eel and basal ganglia: effect on the acetylcholinesterase and aryl acylamidase activities

1984

Majumdar, R.; Balasubramanian, A.S.

Biochemistry

23

4088-4093

208972

16662987

Subcellular localization of rice leaf aryl acylamidase activity

1983

Gaynor, J.J.; Still, C.C.

Plant Physiol.

72

80-85

208977

7035166

The aryl acylamidases and their relationship to cholinesterases in human serum, erythrocyte and liver

1981

George, S.T.; Balasubramanian, A.S.

Eur. J. Biochem.

121

177-186

208979

108100

The association of the serotonin-sensitive aryl acylamidase with acetylcholinesterase in the monkey brain

1979

Oommen, A.; Balasubramanian, A.S.

Eur. J. Biochem.

94

135-143

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

208983

992080

Serotonin-sensitive aryl acylamidase activity of acetylcholinesterase

1976

Fujimoto, D.

FEBS Lett.

71

121-123

208991

-

Rhizobacteria with exceptionally high aryl acylamidase activity

1995

Hoagland, R.E.; Zablotowicz, R.M.

Pestic. Biochem. Physiol.

52

190-200

208996

8294938

Cholinesterases display genuine arylamidase activity but are totally devoid of intrinsic peptidase activities

1994

Checler, F.; Grassi, J.; Vincent, J.P.

J. Neurochem.

62

756-763

208997

1349516

Cholinesterases exhibiting aryl acylamidase activity in human amniotic fluid

1992

Jayanthi, L.D.; Balasubramanian, N.; Balasubramanian, A.S.

Clin. Chim. Acta

205

157-166

209121

237757

Characterization of an inducible amidase from Pseudomonas acidovorans AE1

1975

Alt, J.; Heymann, E.; Krisch, K.

Eur. J. Biochem.

53

357-369

667330

16824479

Diisopropylfluorophosphate-sensitive aryl acylamidase activity of fatty acid free human serum albumin

2006

Manoharan, I.; Boopathy, R.

Arch. Biochem. Biophys.

452

186-188

667928

16504521

On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases

2006

Darvesh, S.; McDonald, R.S.; Darvesh, K.V.; Mataija, D.; Mothana, S.; Cook, H.; Carneiro, K.M.; Richard, N.; Walsh, R.; Martin, E.

Bioorg. Med. Chem.

14

4586-4599

670800

15328888

Aryl acylamidase activity on acetylcholinesterase is high during early chicken brain development

2004

Boopathy, R.; Layer, P.G.

Protein J.

23

325-333

678453

17690023

Kinetic analysis of butyrylcholinesterase-catalyzed hydrolysis of acetanilides

2007

Masson, P.; Froment, M.; Gillon, E.; Nachon, F.; Darvesh, S.; Schopfer, L.M.

Biochim. Biophys. Acta

1774

1139-1147

678541

18208347

Human butyrylcholinesterase components differ in aryl acylamidase activity

2008

Montenegro, M.F.; Moral-Naranjo, M.T.; de la Cadena, M.P.; Campoy, F.J.; Munoz-Delgado, E.; Vidal, C.J.

Biol. Chem.

389

425-432

679183

18452906

The level of aryl acylamidase activity displayed by human butyrylcholinesterase depends on its molecular distribution

2008

Montenegro, M.F.; Moral-Naranjo, M.T.; Paez de la Cadena, M.; Campoy, F.J.; Munoz-Delgado, E.; Vidal, C.J.

Chem. Biol. Interact.

175

336-339

679287

17379201

Human serum cholinesterase from liver pathological samples exhibit highly elevated aryl acylamidase activity

2007

Boopathy, R.; Rajesh, R.V.; Darvesh, S.; Layer, P.G.

Clin. Chim. Acta

380

151-156

697867

18422653

Kinetic analysis of effector modulation of butyrylcholinesterase-catalysed hydrolysis of acetanilides and homologous esters

2008

Masson, P.; Froment, M.T.; Gillon, E.; Nachon, F.; Lockridge, O.; Schopfer, L.M.

FEBS J.

275

2617-2631

697902

19292875

Hydrolysis of acetylthiocoline, o-nitroacetanilide and o-nitrotrifluoroacetanilide by fetal bovine serum acetylcholinesterase

2009

Montenegro, M.F.; Moral-Naranjo, M.T.; Munoz-Delgado, E.; Campoy, F.J.; Vidal, C.J.

FEBS J.

276

2074-2083

711318

19607873

The aryl acylamidase activity is much more sensitive to Alzheimer drugs than the esterase activity of acetylcholinesterase in chicken embryonic brain

2009

Rajesh, R.V.; Chitra, L.; Layer, P.G.; Boopathy, R.

Biochimie

91

1087-1094

711319

19695303

High aryl acylamidase activity associated with cobra venom acetylcholinesterase: biological significance

2009

Rajesh, R.V.; Layer, P.G.; Boopathy, R.

Biochimie

91

1450-1456

752591

26072115

Understanding the molecular mechanism of aryl acylamidase activity of acetylcholinesterase - An in silico study

2015

Chinnadurai, R.K.; Saravanaraman, P.; Boopathy, R.

Arch. Biochem. Biophys.

580

1-13

754722

28852920

The significance of aryl acylamidase activity of acetylcholinesterase in osteoblast differentiation and mineralization

2018

Chinnadurai, R.K.; Saravanaraman, P.; Boopathy, R.

Mol. Cell. Biochem.

440

199-208

Links to other databases for 2-nitroacetanilide

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Show Links (1 entry)

ChEBI

PubChem

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