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Ligand 3-Nitrobenzaldehyde

Basic Ligand Information

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (48 results)

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Show Substrate (48 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

3-nitrobenzaldehyde + NADH + H+ = 3-nitrobenzyl alcohol + NAD+

721868, 722073

-

1.1.1.1

m-nitrobenzaldehyde + NAD+ = m-nitrobenzyl alcohol + NADH + H+

686331

-

1.1.1.1

m-nitrobenzaldehyde + NADH + H+ = m-nitrobenzyl alcohol + NAD+

285604, 697802

-

1.1.1.1

3 entries

1.1.1.112

3-nitrobenzaldehyde + NAD(P)H = 3-nitrobenzyl alcohol + NAD(P)+

285758

-

1.1.1.184

3-nitrobenzaldehyde + NADPH + H+ = 3-nitrobenzyl alcohol + NADP+

711492

-

1.1.1.184

3-nitrobenzaldehyde + NADPH = 3-nitrobenzyl alcohol + NADP+

347758

-

1.1.1.184

3-nitrobenzaldehyde + NADPH = 3-nitrobenzylalcohol + NADP+

655067

-

1.1.1.184

3 entries

1.1.1.19

3-nitrobenzaldehyde + NADPH + H+ = 3-nitrobenzyl alcohol + NADP+

286143

-

1.1.1.2

3-nitrobenzaldehyde + NADH + H+ = 3-nitrobenzyl alcohol + NAD+

286206

-

1.1.1.2

m-nitrobenzaldehyde + NADPH = m-nitrobenzylalcohol + NADP+

286168, 286184, 286165, 286194, 286205, 286181, 286206

-

1.1.1.2

2 entries

1.1.1.21

3-nitrobenzaldehyde + NADPH + H+ = 3-nitrobenzyl alcohol + NADP+

762387

-

1.1.1.274

3-nitrobenzaldehyde + NADPH = 3-nitrobenzyl alcohol + NADP+

669104

-

1.1.1.283

3-nitrobenzaldehyde + NADPH + H+ = 3-nitrobenzyl alcohol + NADP+

670170

-

1.1.1.91

3-nitrobenzaldehyde + NADPH = 3-nitrobenzyl alcohol + NADP+

724669

-

1.1.1.91

m-nitrobenzaldehyde + NADPH = m-nitrobenzyl alcohol + NADP+

389598

-

1.1.1.91

2 entries

1.17.3.2

3-nitrobenzaldehyde + H2O + O2 = 3-nitrobenzoate + H2O2

673434

-

1.2.1.24

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH + H+

700082

-

1.2.1.24

m-nitrobenzaldehyde + NAD+ + H2O = m-nitrobenzoate + NADH

288152

-

1.2.1.24

2 entries

1.2.1.28

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH

390225

-

1.2.1.3

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH + H+

722210

-

1.2.1.3

m-nitrobenzaldehyde + NAD+ + H2O = m-nitrobenzoate + NADH

348717, 348712

-

1.2.1.3

m-nitrobenzaldehyde + NAD+ + H2O = m-nitrobenzoic acid + NADH

671512

-

1.2.1.3

3 entries

1.2.1.32

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH

389581, 390259, 390225

-

1.2.1.4

3-nitrobenzaldehyde + NADP+ + H2O = 3-nitrobenzoate + NADPH + H+

712174

-

1.2.1.5

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH + H+

722210

-

1.2.1.65

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH + 2 H+

741638

-

1.2.1.65

m-nitrobenzaldehyde + NAD+ + H2O = m-nitrobenzoate + NADH + H+

691830

-

1.2.1.65

2 entries

1.2.1.79

3-nitrobenzaldehyde + NADP+ + H2O = 3-nitrobenzoate + NADPH + 2 H+

690736

-

1.2.1.85

3-nitrobenzaldehyde + NAD+ + H2O = 3-nitrobenzoate + NADH + H+

390225

-

1.2.99.7

3-nitrobenzaldehyde + H2O + phenyazine methosulfate = 3-nitrobenzylic acid + reduced phenyazine methosulfate

762827

-

1.3.1.20

3-nitrobenzaldehyde + NADPH = 3-nitrobenzylalcohol + NADP+

349254

-

2.6.1.82

3-nitrobenzaldehyde + cadaverine = 3-nitrobenzylamine + piperideine + H2O

759219

-

2.6.1.82

3-nitrobenzaldehyde + isopropylamine = 3-nitrobenzylamine + acetone + H2O

759219

-

3.4.22.3

cyclohexanone + 3-nitrobenzaldehyde = ?

734500

-

3.4.22.3

tert-butyl 4-oxopiperidine-1-carboxylate + 3-nitrobenzaldehyde = ?

734500

-

3.4.22.3

thian-4-one + 3-nitrobenzaldehyde = ?

734500

-

3.4.23.1

3-nitrobenzaldehyde + 1-hydroxypropan-2-one = (3R,4S)-3,4-dihydroxy-4-(3-nitrophenyl)butan-2-one

755572

-

3.4.23.1

3-nitrobenzaldehyde + cyclohexanone = (2S)-2-[(R)-hydroxy(3-nitrophenyl)methyl]cyclohexan-1-one

755572

-

2.6.1.82

2 entries

3.4.22.3

3 entries

3.4.23.1

2 entries

4.1.2.10

HCN + 3-nitrobenzaldehyde = (R)-2-hydroxy-2-(3-nitrophenyl)acetonitrile

663423

-

4.1.2.42

3-nitrobenzaldehyde + glycine = D-3-nitrophenylserine

682892

-

4.1.2.42

D-alanine + 3-nitrobenzaldehyde = (betaS)-beta-hydroxy-alpha-methyl-3-nitro-D-phenylalanine

691309

-

4.1.2.42

D-alanine + 3-nitrobenzaldehyde = beta-(3-nitrophenyl)-alpha-methyl-serine

746900

-

4.1.2.42

D-serine + 3-nitrobenzaldehyde = beta-(3-nitrophenyl)-alpha-hydroxymethyl-serine

746900

-

4.1.2.42

glycine + 3-nitrobenzaldehyde = (betaS)-beta-hydroxy-3-nitro-D-phenylalanine

691309

-

4.1.2.42

glycine + 3-nitrobenzaldehyde = D-3-(3-nitrophenyl)serine

747468

-

4.1.2.5

D-alanine + 3-nitrobenzaldehyde = beta-(3-nitrophenyl)-alpha-methyl-serine

746900

-

4.1.2.5

D-serine + 3-nitrobenzaldehyde = beta-(3-nitrophenyl)-alpha-hydroxymethyl-serine

746900

-

4.1.2.42

6 entries

4.1.2.5

2 entries

4.2.1.B27

3-nitrobenzaldehyde + nitromethane = 2-nitro-1-(3-nitrophenyl)ethanol

733949

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.90

3-nitrobenzyl alcohol + NAD+ = 3-nitrobenzaldehyde + NADH

0

-

1.1.3.9

3-nitrobenzyl alcohol + O2 = 3-nitrobenzaldehyde + H2O2

389850

-

1.2.1.30

3-nitrobenzoate + NADPH + H+ + ATP = 3-nitrobenzaldehyde + NADP+ + AMP + diphosphate

0

-

4.1.2.48

DL-threo-(3-nitrophenyl)serine = glycine + 3-nitrobenzaldehyde

0

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.1.1.21

40

-

pH 7.0, 45°C

762387

1.1.1.283

1.12

-

1 mM

670170

K_M Value (19 results)

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Show KM Value (19 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.1

1.4

-

isoenzyme ADH-1, pH 7.5

285604

1.1.1.19

0.526

-

-

286143

1.1.1.2

0.002

-

-

286206

1.1.1.2

0.0029

-

-

286205

1.1.1.2

0.082

-

AR2

286181

1.1.1.2

2.4

-

-

286168

1.1.1.2

3.9

-

AR1

286184

1.1.1.2

4

-

AR3

286181

1.1.1.2

4.4

-

-

286194

1.1.1.2

7 entries

1.1.1.21

1.7

-

pH 7.0, 45°C

762387

1.1.1.283

0.91

-

1 mM

670170

1.1.1.91

0.21

-

-

389598

1.17.3.2

0.001

-

pH 7.0

673434

1.2.1.24

0.0502

-

in 100 mM Na2HPO4/NaH2PO4 buffer, 1 mM dithiothreitol, at pH 8.5 and 22°C

700082

1.2.1.24

0.287

-

in 100 mM Na2HPO4/NaH2PO4 buffer, 1 mM dithiothreitol, at pH 8.5 and 22°C

700082

1.2.1.24

2 entries

1.2.1.28

0.022

-

-

390225

1.2.1.32

0.81

-

-

390225, 390259

1.2.1.85

0.81

-

in 100 mM glycine-NaOH (pH 9.2), at 25°C

390225

1.2.99.7

0.22

-

pH 6, 30°C

762827

References & Links

Literature References (48)

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Show Reference (48 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285604

3816781

Characterization of three isoenzymes of rat alcohol dehydrogenase. Tissue distribution and physical and enzymatic properties

1987

Julia, P.; Farres, J.; Pares, X.

Eur. J. Biochem.

162

179-189

285758

2674111

Monkey liver indanol dehydrogenase. Purification, properties, and kinetic mechanism

1989

Hara, A.; Mouri, K.; Nakagawa, M.; Nakamura, M.; Nakayama, T.; Matsuura, K.; Saweda, H.

J. Biochem.

106

126-132

286143

15991

Resolution and partial characterization of two aldehyde reductases of mammalian liver

1977

Tulsiani, D.R.P.; Touster, O.

J. Biol. Chem.

252

2545-2550

286165

4402936

Triphosphopyridine nucleotide-linked aldehyde reductase I. Purification and properties of the enzyme from pig kidney cortex

1972

Bosron, W.F.; Prairie, R.L.

J. Biol. Chem.

217

4480-4485

286168

16919

Purification and properties of NADPH-dependent aldehyde reductase from human liver

1977

Wermuth, B.; Muench, J.D.B.; von Wartburg, J.P.

J. Biol. Chem.

252

3821-3828

286181

6753936

Purification and properties of human liver aldehyde reductases

1982

Petrash, J.M.; Srivastava, S.K.

Biochim. Biophys. Acta

707

105-114

286184

6343086

Isolation and characterization of multiforms of aldehyde reductase in chicken kidney

1983

Hara, A.; Deyashiki, Y.; Nakayama, T.; Sawada, H.

Eur. J. Biochem.

133

207-214

286194

-

A novel NADPH-dependent aldehyde reductase, catalyzing asymmetric reduction of beta-keto acid esters, from Sporobolomyces salmonicolor: purification and characterization

1990

Yamada, H.; Shimizu, S.; Kataoka, M.; Sakai, H.; Miyoshi, T.

FEMS Microbiol. Lett.

70

45-48

286205

9952458

Purification and characterization of a NADPH-dependent aldehyde reductase from mung bean that detoxifies eutypine, a toxin from Eutypa lata1

1999

Colrat, S.; Latche, A.; Guis, M.; Pech, J.C.; Bouzayen, M.; Fallot, J.; Roustan, J.P.

Plant Physiol.

119

621-626

286206

10473548

Structural and enzymatic properties of a gastric NADP(H)-dependent and retinal-active alcohol dehydrogenase

1999

Peralba, J.M.; Cederlund, E.; Crosas, B.; Moreno, A.; Julia, P.; Martinez, S.E.; Persson, B.; Farr s, J.; Pares, X.; Jornvall, H.

J. Biol. Chem.

274

26021-26026

288152

3190233

Human brain high Km aldehyde dehydrogenase: purification, characterization, and identification as NAD+-dependent succinic semialdehyde dehydrogenase

1988

Ryzlak, M.T.; Pietruszko, R.

Arch. Biochem. Biophys.

266

386-396

347758

6439186

Purification and characterization of two forms of microsomal carbonyl reductase in guinea pig liver

1984

Usui, S.; Hara, A.; Nakayama, T.; Sawada, H.

Biochem. J.

223

697-705

348712

223840

Purification and properties of sheep-liver aldehyde dehydrogenases

1979

MacGibbon, A.K.H.; Motion, R.L.

Eur. J. Biochem.

96

585-595

348717

66

Partial purification and properties of a phenobarbital-induced aldehyde dehydrogenase of rat liver

1975

Koivula, T.; Koivusalo, M.

Biochim. Biophys. Acta

410

1-11

349254

7852295

Purification and characterization of dimeric dihydrodiol dehydrogenase from dog liver

1994

Sato, K.; Nakanishi, M.; Deyashiki, Y.; Hara, A.; Matsuura, K.; Ohya, I.

J. Biochem.

116

711-717

389581

2202600

Purification and characterisation of TOL plasmid-encoded benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase of Pseudomonas putida

1990

Shaw, J.P.; Harayama, S.

Eur. J. Biochem.

191

705-714

389598

-

Aromatic alcohol dehydrogenase from potato tubers

1973

Davies, D.D.; Ugochukwu, E.N.; Patil, K.D.; Towers, G.H.N.

Phytochemistry

12

531-536

389850

11401560

Catalytic reaction profile for alcohol oxidation by galactose oxidase

2001

Whittaker, M.M.; Whittaker, J.W.

Biochemistry

40

7140-7148

390225

7868591

Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida

1995

Inoue, J.; Shaw, J.P.; Rekik, M.; Harayama, S.

J. Bacteriol.

177

1196-1201

390259

1590768

Substrate-specificity of benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase encoded by TOL plasmid pWW0

1992

Shaw, J.P.; Schwager, F.; Harayama, S.

Biochem. J.

283

789-794

655067

15665471

Purification and characterization of a yeast carbonyl reductase for synthesis of optically active (R)-styrene oxide derivatives

2005

Kizaki, N.; Sawa, I.; Yano, M.; Yasohara, Y.; Hasegawa, J.

Biosci. Biotechnol. Biochem.

69

79-86

663423

-

A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins

2005

Nanda, S.; Kato, Y.; Asano, Y.

Tetrahedron

61

10908-10916

669104

16077126

Conversion of methylglyoxal to acetol by Escherichia coli aldo-keto reductases

2005

Ko, J.; Kim, I.; Yoo, S.; Min, B.; Kim, K.; Park, C.

J. Bacteriol.

187

5782-5789

670170

16804176

Methylglyoxal detoxification by an aldo-keto reductase in the cyanobacterium Synechococcus sp. PCC 7002

2006

Xu, D.; Liu, X.; Guo, C.; Zhao, J.

Microbiology

152

2013-2021

671512

15812642

Characterization of Sphingomonas aldehyde dehydrogenase catalyzing the conversion of various aromatic aldehydes to their carboxylic acids

2005

Peng, X.; Shindo, K.; Kanoh, K.; Inomata, Y.; Choi, S.K.; Misawa, N.

Appl. Microbiol. Biotechnol.

69

141-150

673434

16715777

Substrate specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase for methyl- and nitrobenzaldehydes

2005

Veskoukis, A.S.; Kouretas, D.; Panoutsopoulos, G.I.

Eur. J. Drug Metab. Pharmacokinet.

31

11-16

682892

-

Threonine aldolases-an emerging tool for organic synthesis

2006

Steinreiber, J.; Fesko, K.; Reisinger, C.; Schuermann, M.; van Assema, F.; Wolberg, M.; Mink, D.; Griengl, H.

Tetrahedron

63

918-926

686331

18224440

The activity of class I, II, III, and IV alcohol dehydrogenase (ADH) isoenzymes and aldehyde dehydrogenase (ALDH) in liver cancer

2008

Jelski, W.; Zalewski, B.; Szmitkowski, M.

Digest. Dis. Sci.

53

2550-2555

690736

18474219

Saturation transfer difference NMR studies on substrates and inhibitors of succinic semialdehyde dehydrogenases

2008

Jaeger, M.; Rothacker, B.; Ilg, T.

Biochem. Biophys. Res. Commun.

372

400-406

691309

18760921

Synthesis of beta-hydroxy-alpha-amino acids with a reengineered alanine racemase

2008

Fesko, K.; Giger, L.; Hilvert, D.

Bioorg. Med. Chem. Lett.

18

5987-5990

691830

-

A novel salicylaldehyde dehydrogenase-NahV involved in catabolism of naphthalene from Pseudomonas putida ND6

2007

Zhao, H.; Li, Y.; Chen, W.; Cai, B.

Chin. Sci. Bull.

52

1942-1948

697802

19332052

The activity of class I, II, III and IV of alcohol dehydrogenase (ADH) isoenzymes and aldehyde dehydrogenase (ALDH) in the wall of abdominal aortic aneurysms

2009

Jelski, W.; Orywal, K.; Panek, B.; Gacko, M.; Mroczko, B.; Szmitkowski, M.

Exp. Mol. Pathol.

87

59-62

700082

18588919

Succinic semialdehyde dehydrogenase from the parasitic cattle tick Rhipicephalus microplus: gene identification, biochemical characterization and comparison with the mouse ortholog

2008

Rothacker, B.; Werr, M.; Ilg, T.

Mol. Biochem. Parasitol.

161

32-43

711492

19574038

A new member of the short-chain dehydrogenases/reductases superfamily: purification, characterization and substrate specificity of a recombinant carbonyl reductase from Pichia stipitis

2009

Ye, Q.; Yan, M.; Yao, Z.; Xu, L.; Cao, H.; Li, Z.; Chen, Y.; Li, S.; Bai, J.; Xiong, J.; Ying, H.; Ouyang, P.

Biores. Technol.

100

6022-6027

712174

20833259

Substrate profiling and aldehyde dismutase activity of the Kvbeta2 subunit of the mammalian Kv1 potassium channel

2010

Alka, K.; Ryan, B.J.; Dolly, J.O.; Henehan, G.T.

Int. J. Biochem. Cell Biol.

42

2012-2018

721868

21670533

Purification and characterization of an NADH-dependent alcohol dehydrogenase from Candida maris for the synthesis of optically active 1-(pyridyl)ethanol derivatives

2011

Kawano, S.; Yano, M.; Hasegawa, J.; Yasohara, Y.

Biosci. Biotechnol. Biochem.

75

1055-1060

722073

21784063

The activity of class I, II, III and IV alcohol dehydrogenase isoenzymes and aldehyde dehydrogenase in cervical cancer

2011

Orywal, K.; Jelski, W.; Zdrodowski, M.; Szmitkowski, M.

Clin. Biochem.

44

1231-1234

722210

23224332

Molecular characterization of a thermostable aldehyde dehydrogenase (ALDH) from the hyperthermophilic archaeon Sulfolobus tokodaii strain 7

2013

Liu, T.; Hao, L.; Wang, R.; Liu, B.

Extremophiles

17

181-190

724669

22742413

Cloning, expression and characterization of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium strain BKM-F-1767

2012

Yang, D.D.; Francois, J.M.; de Billerbeck, G.M.

BMC Microbiol.

12

126

733949

-

Mining catalytic promiscuity from thermophilic archaea: an acyl-peptide releasing enzyme from Sulfolobus tokodaii (ST0779) for nitroaldol reactions

2016

Yu, X.; Pérez, B.; Zhang, Z.; Gao, R.; Guo, Z.

Green Chem.

18

2753-2761

734500

-

Ficin-catalyzed asymmetric aldol reactions of heterocyclic ketones with aldehydes

2013

Fu, J.; Gao, N.; Yang, Y.; Guan, Z.; He, Y.

J. Mol. Catal. B

97

1-4

741638

24122667

Purification and characterization of NAD+-dependent salicylaldehyde dehydrogenase from carbaryl-degrading Pseudomonas sp. strain C6

2014

Singh, R.; Trivedi, V.D.; Phale, P.S.

Appl. Biochem. Biotechnol.

172

806-819

746900

26189018

Expanding the threonine aldolase toolbox for the asymmetric synthesis of tertiary alpha-amino acids

2015

Fesko, K.; Strohmeier, G.A.; Breinbauer, R.

Appl. Microbiol. Biotechnol.

99

9651-9661

747468

-

A new D-threonine aldolase as a promising biocatalyst for highly stereoselective preparation of chiral aromatic beta-hydroxy-alpha-amino acids

2017

Chen, Q.; Chen, X.; Cui, Y.; Ren, J.; Lu, W.; Feng, J.; Wu, Q.; Zhu, D.

Catal. Sci. Technol.

7

5964-5973

755572

-

Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds

2015

Li, L.; Yang, D.; Guan, Z.; He, Y.

Tetrahedron

71

1659-1667

759219

30622946

Characterization of a putrescine transaminase from Pseudomonas putida and its application to the synthesis of benzylamine derivatives

2018

Galman, J.L.; Gahloth, D.; Parmeggiani, F.; Slabu, I.; Leys, D.; Turner, N.J.

Front. Bioeng. Biotechnol.

6

205

762387

-

A halotolerant aldose reductase from Debaryomyces nepalensis gene isolation, overexpression and biochemical characterization

2017

Paidimuddala, B.; Krishna Aradhyam, G.; Gummadi, S.

RSC Adv.

7

20384-20393

762827

32729393

Purification and characterization of molybdenum-containing aldehyde dehydrogenase that oxidizes benzyl maltol derivative from Pseudomonas nitroreducens SB32154

2020

Kozono, I.; Hibi, M.; Takeuchi, M.; Ogawa, J.

Biosci. Biotechnol. Biochem.

84

2390-2400

Links to other databases for 3-Nitrobenzaldehyde

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Show Links (1 entry)

ChEBI

PubChem

-