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BRENDA support

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
BRENDA
degradation of aromatic, nitrogen containing compounds, NAD metabolism, vitamin B12 metabolism
KEGG
Biosynthesis of alkaloids derived from ornithine, lysine and nicotinic acid, Biosynthesis of cofactors, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, Microbial metabolism in diverse environments more
MetaCyc
2-methyladeninyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP, 4-methylphenyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP, 5-hydroxybenzimidazolyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP, 5-methoxy-6-methylbenzimidazolyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP, 5-methoxybenzimidazolyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP more


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)

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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
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In Vivo Product in Enzyme-catalyzed Reactions (35 results)

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

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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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S-adenosyl-L-methionine + nicotinate = S-adenosyl-L-homocysteine + nicotinic acid methyl ester
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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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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Product in Enzyme-catalyzed Reactions (268 results)

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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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Activator in Enzyme-catalyzed Reactions (5 results)

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

Inhibitor in Enzyme-catalyzed Reactions (35 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
weak
-
inhibitory analog of NAD+, non-competitive with respect to IMP and K+
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competitive
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competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+
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potent competitive inhibitor
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65% inhibition at 20 mM
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competitive
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18.3% inhibition at 15 mM
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weak
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weak inhibition
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inhibits the mitochondrial-matrix enzyme activity
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inhibits the mitochondrial-matrix enzyme activity
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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) (360 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.52
-
pH 7.5, 28°C
0.048
-
mutant K185A, at 25°C

KM Value (37 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.036
-
-
0.0162
-
pH 7.0, 23°C
2.75
-
pH 8.0, 21°C
5
-
pH 5, 22°C

Ki Value (12 results)

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

IC50 Value (1 result)

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

References & Links

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Links to other databases for nicotinic acid

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ChEBI
PubChem
ChEBI
PubChem