Ligand nicotinamide

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Basic Ligand Information

Molecular Structure
Picture of nicotinamide (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H6N2O
nicotinamide
DFPAKSUCGFBDDF-UHFFFAOYSA-N
Synonyms:
3-amidopyridine, 3-pyridinecarboxamide, NAM, nicotinic acid amide, pyridine-3-carbamide, pyridine-3-carboxamide


Show all pahtways known for Show all BRENDA pathways known for nicotinamide

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
[protein]-L-lysine + 2''-O-acetyl-ADP-D-ribose + nicotinamide = [protein]-N6-acetyl-L-lysine + NAD+ + H2O
show the reaction diagram
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nicotinamide + Nomega-(ADP-D-ribosyl)-agmatine-L-arginine = NAD+ + agmatine L-arginine
show the reaction diagram
nicotinamide + H2O = nicotinate + NH3
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (149 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
NAD+ + [archaeal chromatin protein Alba]-N6-acyl-L-lysine = nicotinamide + [archaeal chromatin protein Alba]-L-lysine + 2'-O-acyl-ADP-ribose
show the reaction diagram
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NAD+ + 5,6-dimethylbenzimidazole = nicotinamide + alpha-5,6-dimethylbenzimidazole adenine dinucleotide
show the reaction diagram
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NAD+ + glycine + [ADP-thiazole synthase]-L-cysteine = nicotinamide + ADP-5-ethyl-4-methylthiazole-2-carboxylate + [ADP-thiazole synthase]-dehydroalanine + 3 H2O
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NADP+ + nicotinate = nicotinate-adenine dinucleotide phosphate + nicotinamide
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beta-nicotinamide D-riboside + H2O = D-ribose + nicotinamide
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3-cyanopyridine + H2O = nicotinamide
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Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
nicotinamide + Nomega-(ADP-D-ribosyl)-agmatine-L-arginine = NAD+ + agmatine L-arginine
show the reaction diagram
nicotinamide + H2O = nicotinic acid + NH3
show the reaction diagram
-
nicotinamide + H2O = nicotinate + NH3
show the reaction diagram
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nicotinamide + H2O = nicotinate + NH3
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (469 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
electron donor + nicotinamide N-oxide = nicotinamide + electron acceptor
show the reaction diagram
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3-amidopyridine N-oxide + reduced benzyl viologen + H2O = 3-amidopyridine + oxidized benzyl viologen
show the reaction diagram
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NAD+ + [archaeal chromatin protein Alba]-N6-acyl-L-lysine = nicotinamide + [archaeal chromatin protein Alba]-L-lysine + 2'-O-acyl-ADP-ribose
show the reaction diagram
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nicotinamide riboside + phosphate = nicotinamide + alpha-D-ribose 1-phosphate
show the reaction diagram
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NAD+ + glycine + sulfide = nicotinamide + ADP-5-ethyl-4-methylthiazole-2-carboxylate + 3 H2O
show the reaction diagram
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NAD+ + glycine + [ADP-thiazole synthase]-L-cysteine = nicotinamide + ADP-5-ethyl-4-methylthiazole-2-carboxylate + [ADP-thiazole synthase]-dehydroalanine + 3 H2O
show the reaction diagram
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phosphate + nicotinamide riboside = nicotinamide + ribose-1-phosphate
show the reaction diagram
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nicotinamide riboside + H2O = nicotinamide + D-ribose
show the reaction diagram
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nicotinamide riboside + H2O = nicotinamide + D-ribose
show the reaction diagram
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1-beta-D-ribofuranosylnicotinamide + H2O = nicotinamide + D-ribose
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increase of activity
-
enhanced ATPase activity
patients with neurofibromatosis, induction of alkaline phosphodiesterase I
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Inhibitor in Enzyme-catalyzed Reactions (56 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits DPOR activity by blocking the electron transfer from the L-protein to the NB-protein subunit
-
slight inhibition
-
inhibition of the recombinant FAD domain
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the enzyme shows substrate inhibition kinetics
inhibits the deacetylation of native histones much more effectively than deacetylation of a synthetic substrate
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substrate inhibition
inhibition of the cyclization reaction and is 30fold more potent at suppressing the base-exchange reaction. Inhibition is not via a competition with the nicotinic acid-binding site
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SIRT1 inhibitor, potentiates Tat-mediated reduction in AMPK activation and downstream acetyl-CoA carboxylase activation. Potentiates Tat-induced HIV-1 transactivation
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complete inhibition at 25 mM
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inhibits esterolysis of p-nitrophenyl acetate
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19% inhibition at 100 mM
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0.5 M, sharp decrease in activity, low-molecular weight nitrile hydratase; 1.5 M, 40% decrease of activity, high-molecular weight nitrile hydratase
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3D Structure of Enzyme-Ligand-Complex (PDB) (28 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (41 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (69 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

Ki Value (16 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
105
-
pH 7.8, 25°C, substrate: NAD+
122
-
inhibition of the recombinant FAD domain
0.0175
-
wild type enzyme, at pH 8.0 and 25°C

IC50 Value (14 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.7
-
cyclization reaction, pH 7.4, temperature not specified in the publication

References & Links

Links to other databases for nicotinamide

ChEBI
PubChem
ChEBI
PubChem