BRENDA Home

Basic Ligand Information
Roles as Enzyme Ligand
Enzyme Kinetic Parameters
References & Links
- References
- Links

print all entries

Ligand 1-methylnicotinamide

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure

Picture of 1-methylnicotinamide (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₇H₈N₂O

1-methylnicotinamide

LDHMAVIPBRSVRG-UHFFFAOYSA-O

Synonyms:

1-methyl nicotinamide, 3-carbamoyl-1-methylpyridin-1-ium, MNA+, N-methylnicotinimidamide, N1-(methyl)-nicotinamide, N1-methyl-nicotineamide, N1-methylnicotinamide

Pathway Source

Pathways

KEGG

Bile secretion, Nicotinate and nicotinamide metabolism

close all tables

open all tables

Roles as Enzyme Ligand

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

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.1

L-methionine + nicotinamide = L-homocysteine + 1-methylnicotinamide

5xvk, 3D-view

2.1.1.1

S-adenosyl-L-methionine + nicotinamide = S-adenosyl-L-homocysteine + 1-methylnicotinamide

5xvk, 3D-view

2.1.1.1

2 entries

Substrate in Enzyme-catalyzed Reactions (6 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Substrate (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.3.2

N1-methylnicotinamide + H2O + O2 = ?

644625, 393008

1.2.3.1

N1-methyl-nicotineamide + H2O + 2,6-dichlorophenolindophenol = ? + reduced 2,6-dichlorophenolindophenol

741285

1.2.3.1

N1-methylnicotinamide + 2,6-dichlorophenol indophenol = ?

725498

1.2.3.1

N1-methylnicotinamide + H2O + O2 = N1-methyl-2-pyridone-5-carboxamide + N1-methyl-4-pyridone-3-carboxamide + ?

673297

1.2.3.1

N1-methylnicotinamide + H2O + O2 = N1-methyl-2-pyridone-5-carboxamide + N1-methyl-4-pyridone-3-carboxamide + H2O2

390376, 390401, 390415, 691701, 691884, 692051, 390412, 390413, 390414, 762958, 390378, 390397, 390389, 390394, 390396, 390391, 390416

1.2.3.1

4 entries

3.5.1.19

1-methylnicotinamide + H2O = 1-methylnicotinate + NH3

718924

Product in Enzyme-catalyzed Reactions (6 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.10.5.1

reduced N1-(methyl)-nicotinamide + menadione = N1-(methyl)-nicotinamide + reduced menadiol

1.6.3.4

MNAH + H+ + O2 = MNA+ + H2O

2.1.1.1

L-methionine + nicotinamide = L-homocysteine + 1-methylnicotinamide

5xvk, 3D-view

2.1.1.1

nicotinamide + S-adenosyl-L-methionine = 1-methylnicotinamide + S-adenosyl-L-homocysteine

5xvk, 3D-view

2.1.1.1

S-adenosyl-L-methionine + nicotinamide = S-adenosyl-L-homocysteine + 1-methylnicotinamide

5xvk, 3D-view

2.1.1.1

S-adenosyl-L-methionine + nicotinimidamide = S-adenosyl-L-homocysteine + N-methylnicotinimidamide

5xvk, 3D-view

2.1.1.1

4 entries

Inhibitor in Enzyme-catalyzed Reactions (5 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

feedback inhibitor

product inhibition

IC50 0.06 mM for human protein, 0.03 mM for recombinant protein

33% inhibition at 1 mM

637795

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (1 entry)

EC NUMBER

ENZYME 3D STRUCTURE

2.1.1.1

5xvk, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (11 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Turnover Number (11 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.2.3.1

0.052

K889H mutant, pH 8.0, 37°C

725498

1.2.3.1

0.187

A807V mutant, pH 8.0, 37°C

725498

1.2.3.1

0.245

mAOX3 wild type, pH 8.0, 37°C

725498

1.2.3.1

0.33

pH 8, 37°C

762958

1.2.3.1

0.38

mutant F1014V, pH 8.0,37°C

741285

1.2.3.1

0.39

Y885M mutant, pH 8.0, 37°C

725498

1.2.3.1

0.4

wild-type, pH 8.0,37°C

741285

1.2.3.1

0.45

A807V/Y885M double mutant, pH 8.0, 37°C

725498

1.2.3.1

0.82

pH 8, 37°C

762958

1.2.3.1

1.08

mutant P1015A, pH 8.0,37°C

741285

1.2.3.1

1.92

mutant P1015G, pH 8.0,37°C

741285

1.2.3.1

11 entries

K_M Value (11 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show KM Value (11 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.2.3.1

0.0094

pH 8, 37°C

762958

1.2.3.1

0.0255

K889H mutant, pH 8.0, 37°C

725498

1.2.3.1

0.0279

pH 8, 37°C

762958

1.2.3.1

0.0359

A807V/Y885M double mutant, pH 8.0, 37°C

725498

1.2.3.1

0.0827

Y885M mutant, pH 8.0, 37°C

725498

1.2.3.1

0.087

mutant P1015A, pH 8.0,37°C

741285

1.2.3.1

0.089

mutant P1015G, pH 8.0,37°C

741285

1.2.3.1

0.1234

A807V mutant, pH 8.0, 37°C

725498

1.2.3.1

0.128

wild-type, pH 8.0,37°C

741285

1.2.3.1

0.1285

mAOX3 wild type, pH 8.0, 37°C

725498

1.2.3.1

0.482

mutant F1014V, pH 8.0,37°C

741285

1.2.3.1

11 entries

IC₅₀ Value (2 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show IC50 Value (2 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.1.1.1

0.023

substrate quinoline, pH 8.6, 37°C

756053

2.1.1.1

0.06

IC50 0.06 mM for human protein, 0.03 mM for recombinant protein

441255

2.1.1.1

2 entries

References & Links

Literature References (29)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Reference (29 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

390376

10598038

Purification and some properties of hamster liver aldehyde oxidase

1999

Sugihara, K.; Katsuma, Y.; Tanaka, C.; Kitamura, S.

Biol. Pharm. Bull.

1246-1248

390378

9920943

cDNA cloning, sequencing, and characterization of male and female rat liver aldehyde oxidase (rAOX1)

1999

Wright, R.M.; Clayton, D.A.; Riley, M.G.; McManaman, J.L.; Repine, J.E.

J. Biol. Chem.

274

3878-3886

390389

3778470

Tropylium tetrafluoroborate, a novel substrate for aldehyde oxidase

1986

Banks, R.B.; Barnett, S.D.

Biochem. Biophys. Res. Commun.

140

609-615

390391

2941018

Chromate reduction by rabbit liver aldehyde oxidase

1986

Banks, R.B.; Cooke, R.T.

Biochem. Biophys. Res. Commun.

137

8-14

390394

3789740

Aldehyde oxidase from rabbit liver: specificity toward purines and their analogs

1986

Hall, W.W.; Krenitsky, T.A.

Arch. Biochem. Biophys.

251

36-46

390396

4051501

Guinea pig liver aldehyde oxidase as a sulfoxide reductase: its purification and characterization

1985

Yoshihara, S.; Tatsumi, K.

Arch. Biochem. Biophys.

242

213-224

390397

2994572

Oxidation in H2O and D2O of 6-ethyl-5H-dibenz(c,e)azepine and 1-methylnicotinamide by aldehyde oxidase from rabbit liver

1985

Thomas, H.G.; Silverman, D.N.

Arch. Biochem. Biophys.

241

649-655

390401

6743274

Simultaneous formation of 2- and 4-quinolones from quinolinium cations catalysed by aldehyde oxidase

1984

Taylor, S.M.; Stubley-Beedham, C.; Stell, J.G.P.

Biochem. J.

220

67-74

390412

4698232

Purification and properties of the aldehyde oxidases from hog and rabbit livers

1973

Felsted, R.L.; Chu, A.E.Y.; Chaykin, S.

J. Biol. Chem.

248

2580-2587

390413

Iron-sulfur flavoprotein hydrolases

1973

Massey, V.

Iron-Sulfur Proteins (Lovenberg, W. , ed. )

301-360

390414

5044040

A comparison of the specificities of xanthine oxidase and aldehyde oxidase

1972

Krenitsky, T.A.; Neil, S.M.; Elion, G.B.; Hitchings, G.H.

Arch. Biochem. Biophys.

150

585-599

390415

4256441

Aldehyde oxidase: catalysis of the oxidation of N 1 -methylnicotinamide and pyridoxal

1971

Stanulovic, M.; Chaykin, S.

Arch. Biochem. Biophys.

145

27-34

390416

4244885

Substrate-induced chemiluminescence of xanthine oxidase and aldehyde oxidase

1970

Arneson, R.M.

Arch. Biochem. Biophys.

136

352-360

393008

Molybdenum iron-sulfur flavin hydroxylases and related enzymes

1975

Bray, R.C.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

299-419

441253

2311261

Human liver nicotinamide N-methyltransferase: ion-pairing radiochemical assay, biochemical properties and individual variation

1990

Rini, J.; Szumlanski, C.; Guerciolini, R.; Weinshilboum, R.M.

Clin. Chim. Acta

186

359-374

441255

8182091

Human liver nicotinamide N-methyltransferase. cDNA cloning, expression, and biochemical characterization

1994

Aksoy, S.; Szumlanski, C.L.; Weinshilboum, R.M.

J. Biol. Chem.

269

14835-14840

637795

Finding of UDP-glucose:nicotinic acid-N-glucosyltransferase activity in cultured tobacco cells and its properties

1997

Taguchi, H.; Sasatani, K.; Nishitani, H.; Okumura, K.

Biosci. Biotechnol. Biochem.

720-722

644625

3010873

Xanthine oxidase from human liver: purification and characterization

1986

Krenitsky, T.A.; Spector, T.; Hall, W.W.

Arch. Biochem. Biophys.

247

108-119

673297

16299165

Estimation of aldehyde oxidase activity in vivo from conversion ratio of N1-methylnicotinamide to pyridones, and intraspecies variation of the enzyme activity in rats

2006

Sugihara, K.; Tayama, Y.; Shimomiya, K.; Yoshimoto, D.; Ohta, S.; Kitamura, S.

Drug Metab. Dispos.

208-212

691701

18066686

Mammalian aldehyde oxidases: genetics, evolution and biochemistry

2008

Garattini, E.; Fratelli, M.; Terao, M.

Cell. Mol. Life Sci.

1019-1048

691884

17375106

Developmental changes of aldehyde oxidase activity in young Japanese children

2007

Tayama, Y.; Miyake, K.; Sugihara, K.; Kitamura, S.; Kobayashi, M.; Morita, S.; Ohta, S.; Kihira, K.

Clin. Pharmacol. Ther.

567-572

692051

17495419

Developmental changes of aldehyde oxidase in postnatal rat liver

2007

Tayama, Y.; Moriyasu, A.; Sugihara, K.; Ohta, S.; Kitamura, S.

Drug Metab. Pharmacokinet.

119-124

701990

18996527

Adipose tissue as a source of nicotinamide N-methyltransferase and homocysteine

2009

Riederer, M.; Erwa, W.; Zimmermann, R.; Frank, S.; Zechner, R.

Atherosclerosis

204

412-417

718924

22229411

Structural and kinetic isotope effect studies of nicotinamidase (Pnc1) from Saccharomyces cerevisiae

2012

Smith, B.C.; Anderson, M.A.; Hoadley, K.A.; Keck, J.L.; Cleland, W.W.; Denu, J.M.

Biochemistry

243-256

725498

23019336

The first mammalian aldehyde oxidase crystal structure: insights into substrate specificity

2012

Coelho, C.; Mahro, M.; Trincao, J.; Carvalho, A.T.; Ramos, M.J.; Terao, M.; Garattini, E.; Leimkuehler, S.; Romao, M.J.

J. Biol. Chem.

287

40690-40702

741285

24358164

Identification of crucial amino acids in mouse aldehyde oxidase 3 that determine substrate specificity

2013

Mahro, M.; Bras, N.F.; Cerqueira, N.M.; Teutloff, C.; Coelho, C.; Romao, M.J.; Leimkuehler, S.

PLoS ONE

e82285

755958

28720493

Crystal structures of monkey and mouse nicotinamide N-methyltransferase (NNMT) bound with end product, 1-methyl nicotinamide

2017

Swaminathan, S.; Birudukota, S.; Thakur, M.K.; Parveen, R.; Kandan, S.; Juluri, S.; Shaik, S.; Anand, N.N.; Burri, R.R.; Kristam, R.; Hallur, M.S.; Rajagopal, S.; Schreuder, H.; Langer, T.; Rudolph, C.; Ruf, S.; Dhakshinamoorthy, S.; Gosu, R.; Kannt, A.

Biochem. Biophys. Res. Commun.

491

416-422

756053

30148963

Kinetic mechanism of nicotinamide N-methyltransferase

2018

Loring, H.S.; Thompson, P.R.

Biochemistry

5524-5532

762958

28526768