Ligand nicotinic acid

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Basic Ligand Information

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

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
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
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nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate + ATP + H2O = beta-nicotinate D-ribonucleotide + diphosphate + ADP + phosphate
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
isopyridoxal + NAD+ + H2O = 5-pyridoxate + NADH + H+
show the reaction diagram
-
-
nicotinamide + H2O = nicotinate + NH3
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-pyridoxic acid + NADPH + O2 + H3O+ = 2-(acetylaminomethylene)succinate + NADP+ + H2O
show the reaction diagram
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nicotinate + [reduced NADPH-hemoprotein reductase] + O2 = ?
show the reaction diagram
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nicotinic acid + acceptor = 6-hydroxynicotinic acid + reduced acceptor
show the reaction diagram
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nicotinic acid + acceptor + H2O = 6-hydroxynicotinic acid + reduced acceptor
show the reaction diagram
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nicotinic acid + UDP-glucose = ?
show the reaction diagram
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nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate + ATP + H2O = beta-nicotinate D-ribonucleotide + diphosphate + ADP + phosphate
show the reaction diagram
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thiamine + 3-pyridinecarboxylic acid = 4-methyl-5-(2-hydroxyethyl)-thiazole + 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-carboxypyridinium
show the reaction diagram
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NADP+ + nicotinic acid = nicotinic acid adenine dinucleotide phosphate
show the reaction diagram
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ATP + nicotinate + CoA = AMP + diphosphate + nicotinyl-CoA
show the reaction diagram
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nicotinate + 5-phospho-alpha-D-ribose 1-diphosphate + ATP + H2O = beta-nicotinate D-ribonucleotide + diphosphate + ADP + phosphate
show the reaction diagram

Product in Enzyme-catalyzed Reactions (279 results)

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

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, activity of both isoenzymes is modestly enhanced
-

Inhibitor in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
COMMENTARY
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+
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potent competitive inhibitor
-
65% inhibition at 20 mM
-
competitive
-
18.3% inhibition at 15 mM
-
weak
-
weak inhibition
-
inhibits the mitochondrial-matrix enzyme activity
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inhibits the mitochondrial-matrix enzyme activity
-
non-competitive inhibitor, Ki: 4.4 mM
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inhibition at concentrations greater than 0.2 M
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3D Structure of Enzyme-Ligand-Complex (PDB) (20 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.048
-
mutant K185A, at 25C

KM Value (36 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.036
-
-
2.75
-
pH 8.0, 21C
5
-
pH 5, 22C

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.7
-
pH 8.0, 25C
0.5
-
-
0.49
-
-
0.06
-
-
0.023
-
-
0.7
-
pH 8.0, 25C
9
-
pH 7.2, 37C, purified enzyme
4.4
-
-

IC50 Value (1 result)

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

References & Links

Links to other databases for nicotinic acid

ChEBI
PubChem
ChEBI
PubChem