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• • In Vivo Substrate
  • In Vivo Product
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  • Activator
  • Inhibitor
  • Metals and Ions
  • 3D Structure (PDB)
• Enzyme Kinetic Parameters
• • k_cat Value (Turnover Number)
  • K_M Value
  • K_i Value
  • IC₅₀ Value
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• • References
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Ligand 6-Hydroxynicotinate

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

1.14.13.114

6-hydroxynicotinate + NADH + H+ + O2 = 2,5-dihydroxypyridine + NAD+ + H2O + CO2

700940, 744353, 697700

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.1.5

nicotinate + H2O + electron acceptor = 6-hydroxynicotinate + reduced electron acceptor

644529, 644530, 644533, 644532

-

1.17.1.5

nicotinate + H2O + NAD+ = 6-hydroxynicotinate + NADH + H+

-

-

1.17.1.5

nicotinate + H2O + NADP+ = 6-hydroxynicotinate + NADPH

644534

-

1.17.1.5

nicotinate + H2O + NADP+ = 6-hydroxynicotinate + NADPH + H+

-

-

1.17.1.5

4 entries

1.3.7.1

1,4,5,6-tetrahydro-6-oxonicotinate + oxidized ferredoxin = 6-hydroxynicotinate + reduced ferredoxin

391151

-

Substrate in Enzyme-catalyzed Reactions (12 results)

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Show Substrate (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.114

6-hydroxynicotinate + NADH + H+ + O2 = 2,5-dihydroxypyridine + NAD+ + H2O + CO2

700940, 744353, 697700

-

1.17.3.3

6-hydroxynicotinate + H2O + 2,6-dichlorophenol indophenol = 2,6-dihydroxynicotinate + H2O2 + reduced 2,6-dichlorophenol indophenol

644533

-

1.17.3.3

6-hydroxynicotinate + H2O + methylene blue = 2,6-dihydroxynicotinate + H2O2 + reduced methylene blue

644533

-

1.17.3.3

6-hydroxynicotinate + H2O + nitroblue tetrazolium chloride = 2,6-dihydroxynicotinate + H2O2 + reduced nitroblue tetrazolium chloride

644533

-

1.17.3.3

6-hydroxynicotinate + H2O + O2 = 1,4,5,6-tetrahydro-6-oxonicotinate + H2O2

670692

-

1.17.3.3

6-hydroxynicotinate + H2O + O2 = 2,6-dihydroxynicotinate + H2O2

644532, 391423, 644533

-

1.17.3.3

6-hydroxynicotinate + H2O + phenazine ethosulfate = 2,6-dihydroxynicotinate + H2O2 + reduced phenazine ethosulfate

644533

-

1.17.3.3

6-hydroxynicotinate + H2O + thiazolyl blue = 2,6-dihydroxynicotinate + H2O2 + reduced thiazolyl blue

644533

-

1.17.3.3

6-hydroxynicotinate + H2O + thionin = 2,6-dihydroxynicotinate + H2O2 + reduced thionin

644533

-

1.3.7.1

6-hydroxynicotinate + reduced ferredoxin = 1,4,5,6-tetrahydro-6-oxonicotinate + oxidized ferredoxin

670692

-

1.3.7.1

6-hydroxynicotinate + reduced ferredoxin = 6-oxo-1,4,5,6-tetrahydronicotinate + oxidized ferredoxin

391150

-

1.3.7.1

6-hydroxynicotinate + reduced methyl viologen = 6-oxo-1,4,5,6-tetrahydronicotinate + oxidized methyl viologen

391150

-

1.17.3.3

8 entries

1.3.7.1

3 entries

Product in Enzyme-catalyzed Reactions (12 results)

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Show Product (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.17.1.5

pyridine-3-carboxylate + NADP+ + H2O = 6-hydroxy-pyridine-3-carboxylate + NADPH + H+

-

-

1.17.1.5

nicotinate + H2O + 2,6-dichloroindophenol = 6-hydroxynicotinate + reduced 2,6-dichloroindophenol

-

-

1.17.1.5

nicotinate + H2O + electron acceptor = 6-hydroxynicotinate + reduced electron acceptor

644529, , 644533, 644532, 644530

-

1.17.1.5

nicotinate + H2O + NAD+ = 6-hydroxynicotinate + NADH + H+

-

-

1.17.1.5

nicotinate + H2O + NADP+ = 6-hydroxynicotinate + NADPH

, 644534, 644535, 644528

-

1.17.1.5

nicotinate + H2O + NADP+ = 6-hydroxynicotinate + NADPH + H+

-

-

1.17.1.5

nicotinate + H2O + phenazine methosulfate = 6-hydroxynicotinate + reduced phenazine methosulfate

-

-

1.17.2.1

nicotinic acid + 5-methylphenazinium methyl sulfate + H2O = 6-hydroxynicotinate + ?

-

-

1.17.2.1

nicotinic acid + 5-methylphenazinium methyl sulfate + H2O = 6-hydroxynicotinic acid + ?

-

-

1.17.1.5

7 entries

1.17.2.1

2 entries

1.3.7.1

1,4,5,6-tetrahydro-6-oxonicotinate + oxidized ferredoxin = 6-hydroxynicotinate + reduced ferredoxin

391151, 391150

-

1.3.99.18

nicotinic acid + acceptor = 6-hydroxynicotinic acid + reduced acceptor

12576

-

1.5.99.4

nicotinic acid + acceptor + H2O = 6-hydroxynicotinic acid + reduced acceptor

392538, 392543, 392542

-

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.2

-

390026

-

1.14.13.2

at high concentrations

390019

-

1.14.13.2

2 entries

1.17.1.5

inhibits effectively

644535

-

1.2.99.6

-

11939

-

1.3.1.57

tested at 1.0 mM, 12% inhibition

288477

-

2.4.1.196

73% inhibition at 1 mM

637795

-

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

1.14.13.114

2.2

-

pH 7.5, 25°C

744353

1.14.13.114

4.2

-

pH 7.5, 25°C

744353

1.14.13.114

2 entries

K_M Value (4 results)

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Show KM Value (4 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.13.114

0.085

-

pH 7.5, 25°C

744353

1.14.13.114

0.097

-

pH 7.5, 25°C

744353

1.14.13.114

0.098

-

pH 7.0, 30°C

697700

1.14.13.114

3 entries

1.17.3.3

0.8

-

pH 7.5, 30°C

644533

References & Links

Literature References (23)

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Show Reference (23 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

11939

-

Pterin cofactor, substrate specificity, and observations on the kinetics of the reversible tungsten-containing aldehyde oxidoreductase from Clostridium thermoaceticum

1995

Huber, C.; Skopan, H.; Feicht, R.; White, H.; Simon, H.

Arch. Microbiol.

164

110-118

12576

8357532

XVIII. Purification and some properties of the molybdenum- and iron-containing quinaldic acid 4-oxidoreductase from Serratia marcescens 2CC-1

1993

Fetzner, S.; Lingens, F.

Biol. Chem. Hoppe-Seyler

374

363-376

288477

2925649

Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41

1989

Haddock, J.D.; Ferry, J.G.

J. Biol. Chem.

264

4423 - 4427

390019

4402938

Studies on the effector specificity of p-hydroxybenzoate hydroxylase from Pseudomonas fluorescens

1972

Spector, T.; Massey, V.

J. Biol. Chem.

247

4679-4687

390026

2177819

Hydroxybenzoate hydroxylase

1990

Entsch, B.

Methods Enzymol.

188

138-147

391150

5767303

Nicotinic acid metabolism. IV. Ferredoxin-dependent reduction of 6-hydroxynicotinic acid to 6-oxo-1,4,5,6-tetrahydronicotinic acid

1969

Holcenberg, J.S.; Tsai, L.

J. Biol. Chem.

244

1204-1211

391151

1447145

Elucidation of the complete Azorhizobium nicotinate catabolism pathway

1992

Kitts, C.L.; Lapointe, J.P.; Lam, V.T.; Ludwig, R.A.

J. Bacteriol.

174

7791-7797

391423

-

Bactopterin as component of eubacterial dehydrogenases involved in hydroxylation reactions initiating the degradation of nicotine, nicotinate, and 2-furancarboxylate

1989

Nagel, M.; Koenig, K.; Andreesen, J.R.

FEMS Microbiol. Lett.

60

323-326

392538

4962139

The purification and properties of nicotine oxidase

1967

Hochstein, L.L.; Dalton, B.P.

Biochim. Biophys. Acta

139

56-68

392542

4354821

Cytochrome c linked nicotinic acid hydroxylase in Pseudomonas ovalis chester

1973

Jones, M.V.

FEBS Lett.

32

321-324

392543

13475371

The bacterial oxidation of nicotinic acid

1957

Behrman, E.J.; Stanier, R.Y.

J. Biol. Chem.

228

923-945

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.

61

720-722

644528

8278371

Nicotinic acid hydroxylase from Clostridium barkeri: Electron paramagnetic resonance studies show that selenium is coordinated with molybdenum in the catalytically active selenium-dependent enzyme

1994

Gladyshev, V.N.; Khangulov, S.V.; Stadtman, T.C.

Proc. Natl. Acad. Sci. USA

91

232-236

644529

-

Purification and characterization of nicotinic acid dehydrogenase from Pseudomonas fluorescens TN5

1994

Hurh, B.; Yamane, T.; Nagasawa, T.

J. Ferment. Bioeng.

78

19-26

644530

5128334

Oxidation of nicotinic acid by a Bacillus species: purification and properties of nicotinic acid and 6-hydroxynicotinic acid hydroxylases

1971

Hirschberg, R.; Ensign, J.C.

J. Bacteriol.

108

751-756

644532

-

Molybdenum-dependent degradation of nicotinic acid by Bacillus sp. DSM 2923

1989

Nagel, M.; Andreesen, J.R.

FEMS Microbiol. Lett.

59

147-152

644533

-

Purification and characterization of the molybdoenzymes nicotinate dehydrogenase and 6-hydroxynicotinate dehydrogenase from Bacillus niacini

1990

Nagel, M.; Andreesen, J.R.

Arch. Microbiol.

154

605-613

644534

4388026

Nicotinic acid metabolism. III. Purification and properties of a nicotinic acid hydroxylase

1969

Holcenberg, J.S.; Stadtman, E.R.

J. Biol. Chem.

244

1194-1203

644535

8555176

Properties of the selenium- and molybdenum-containing nicotinic acid hydroxylase from Clostridium barkeri

1996

Gladyshev, V.N.; Khangulov, S.V.; Stadtman, T.C.

Biochemistry

35

212-223

670692

16894175

Molecular and functional analysis of nicotinate catabolism in Eubacterium barkeri

2006

Alhapel, A.; Darley, D.J.; Wagener, N.; Eckel, E.; Elsner, N.; Pierik, A.J.

Proc. Natl. Acad. Sci. USA

103

12341-12346

697700

10091591

Purification, characterization and gene cloning of 6-hydroxynicotinate 3-monooxygenase from Pseudomonas fluorescens TN5

1999

Nakano, H.; Wieser, M.; Hurh, B.; Kawai, T.; Yoshida, T.; Yamane, T.; Nagasawa, T.

Eur. J. Biochem.

260

120-126

700940

18678916

Deciphering the genetic determinants for aerobic nicotinic acid degradation: The nic cluster from Pseudomonas putida KT2440

2008

Jimenez, J.; Canales, A.; Jimenez-Barbero, J.; Ginalski, K.; Rychlewski, L.; Garcia, J.; Diaz, E.

Proc. Natl. Acad. Sci. USA

105

11329-11334

744353

27218267

Structural and biochemical characterization of 6-hydroxynicotinic acid 3-monooxygenase, a novel decarboxylative hydroxylase involved in aerobic nicotinate degradation

2016

Hicks, K.; Yuen, M.; Zhen, W.; Gerwig, T.; Story, R.; Kopp, M.; Snider, M.

Biochemistry

55

3432-3446

Links to other databases for 6-Hydroxynicotinate

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Show Links (1 entry)

ChEBI

PubChem

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