Ligand nicotinate

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Basic Ligand Information

Molecular Structure
Picture of nicotinate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H5NO2
nicotinate
PVNIIMVLHYAWGP-UHFFFAOYSA-N
Synonyms:
3-carboxypyridine, 3-pyridinecarboxylate, 3-pyridinecarboxylic acid, 3-pyridine carboxylic acid, 5-pyridoxate, 5-pyridoxic acid, beta-picolinic acid, niacin, nicotinic acid, nictotinic acid, pyridin-3-formiate, pyridine-3-carboxylate, pyridine-3-carboxylic acid, pyridine 3-carboxylate, pyridine 3-carboxylic acid, vitamin B3
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for nicotinate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
5-pyridoxic acid + NADH + O2 + H+ = 2-(acetamidomethylene)-beta-hydroxymethyl succinate + NAD+
-
show the reaction diagram
UDPglucose + nicotinate = ?
-
show the reaction diagram
NADP+ + nicotinate = nicotinate-adenine dinucleotide phosphate + nicotinamide
-
show the reaction diagram
nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate + ATP + H2O = beta-nicotinate D-ribonucleotide + diphosphate + ADP + phosphate
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In Vivo Product in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
isopyridoxal + NAD+ + H2O = 5-pyridoxate + NADH + H+
-
-
show the reaction diagram
nicotinamide + H2O = nicotinate + NH3
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Substrate in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
5-pyridoxic acid + NADPH + O2 + H3O+ = 2-(acetylaminomethylene)succinate + NADP+ + H2O
-
show the reaction diagram
nicotinate + [reduced NADPH-hemoprotein reductase] + O2 = ?
-
show the reaction diagram
nicotinic acid + acceptor = 6-hydroxynicotinic acid + reduced acceptor
-
show the reaction diagram
nicotinic acid + acceptor + H2O = 6-hydroxynicotinic acid + reduced acceptor
-
show the reaction diagram
S-adenosyl-L-methionine + nicotinate = S-adenosyl-L-homocysteine + nicotinic acid methyl ester
-
show the reaction diagram
nicotinic acid + UDP-glucose = ?
-
show the reaction diagram
nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate + ATP + H2O = beta-nicotinate D-ribonucleotide + diphosphate + ADP + phosphate
-
show the reaction diagram
NADP+ + nicotinic acid = nicotinic acid adenine dinucleotide phosphate
-
show the reaction diagram
ATP + nicotinate + CoA = AMP + diphosphate + nicotinyl-CoA
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Product in Enzyme-catalyzed Reactions (268 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
3-chloropyridine + H2O2 = 3-chloropyridine N-oxide + nicotinic alcohol + nicotinic aldehyde + nicotinic acid + H2O
-
-
show the reaction diagram
isopyridoxal + NAD+ + H2O = 5-pyridoxate + NADH + H+
-
-
show the reaction diagram
3-pyridine carboxaldehyde + NAD+ + H2O = 3-pyridine carboxylic acid + NADH + 2 H+
-
show the reaction diagram
pyridin-3-carboxyaldehyde + NAD+ + H2O = pyridin-3-formiate + NADH
-
-
show the reaction diagram
3-pyridinecarboxaldehyde + H2O + 2,6-dichlorophenol-indophenol = 3-pyridinecarboxylate + reduced 2,6-dichlorophenol-indophenol
-
-
show the reaction diagram
nicotinic acid N-oxide + (ferrocytochrome c)-subunit + H+ = nicotinic acid + (ferricytochrome c)-subunit + H2O
-
-
show the reaction diagram
3-carboxypyridine N-oxide + reduced benzyl viologen + H2O = 3-carboxypyridine + oxidized benzyl viologen
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show the reaction diagram
nicotinic acid mononucleotide + H2O = nicotinic acid + ribose 5-phosphate
-
-
show the reaction diagram
nicotinic acid riboside + H2O = nicotinic acid + D-ribose
-
-
show the reaction diagram
nicotinamide + H2O = nicotinic acid + NH3
-
-
show the reaction diagram
nicotinamide + H2O = nicotinate + NH3
-
-
show the reaction diagram
nicotinamide + H2O = nicotinate + NH3
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Activator in Enzyme-catalyzed Reactions (5 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (35 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
weak
-
inhibitory analog of NAD+, non-competitive with respect to IMP and K+
-
competitive
-
competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
-
potent competitive inhibitor
-
competitive with 3-hydroxy-2-methylpyridine-5-carboxylate
-
competitive
-
65% inhibition at 20 mM
-
competitive
-
D-phenylglycine oxidation
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ferrileghemoglobin-nitrite complex
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a specific noncompetitive DGAT2 inhibitor. Dga1p enzyme mutant versions exhibit DGAT2 specific activity, which is inhibited by niacin. The decrease is 70% for Dga1pDELTA19 and up to 99.5% for Dga1pDELTA85
-
30% inhibition
-
18.3% inhibition at 15 mM
-
weak
-
weak inhibition
-
inhibits the mitochondrial-matrix enzyme activity
slight inhibition, in vivo
-
competitive inhibition
inhibits amidase and esterase activity
competitive inhibition
non-competitive inhibitor, Ki: 4.4 mM
-
inhibition at concentrations greater than 0.2 M
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3D Structure of Enzyme-Ligand-Complex (PDB) (360 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 7.5, 28°C
3.52
-
mutant K185A, at 25°C
0.048
-
in the presence of phosphate, pH 7.5, 37°C
0.25
-
pH 7.5, 37°C
0.012
-

KM Value (37 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
recombinant enzyme, with phenazine methosulfate, pH 7.0, 30°C
0.0659
-
pH 7.0, 35°C
0.0125
-
pH 7.5, 28°C
0.0387
-
pH 7.0, 23°C
0.0162
-
pH 8.0, 21°C
2.75
-
mutant K185A, at 25°C
0.151
-
-
0.01
-
pH 5, 22°C
5
-
reduced to 0.0005 mM in the presence of ATP
0.024
-
pncB gene, in the uncoupled reaction
0.29
-
pncB gene, in the coupled reaction
0.0015
-
pH 7.5, 37°C
0.0443
-
reduced to 0.053 mM in the presence of ATP
0.22
-
mutant enzymes
0.33
0.4
in the presence of phosphate, pH 7.5, 37°C
0.0273
-
in the presence of ATP
0.0005
-
+/-3.6 microM, in presence of 1 mM NAD+, 80 ng enzyme, 10-70 microM nicotinamide, 0.3 mM PRPP, 30 min, 37°C, TLC-based quantification
0.0127
-
+/-3.4 microM, 80 ng enzyme, 10-70 microM nicotinamide, 0.3 mM PRPP, 30 min, 37°C, TLC-based quantification
0.0155
-

Ki Value (12 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
pH 8.0, 25°C
0.7
-
-
0.5
-
competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
pH 8.0, 25°C
0.7
-
pH 7.2, 37°C, purified enzyme
9
-
in 100 mM phosphate buffer, pH 7.3 at 25°C
2
-
wild type enzyme, in 50 mM sodium phosphate (pH 7.5), at 25°C
0.12
-
-
4.4
-

IC50 Value (1 result)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
at pH 8.3 and 37°C
2.778
-

References & Links

Links to other databases for nicotinate

ChEBI
PubChem
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PubChem