Ligand Nicotine

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Basic Ligand Information

Molecular Structure
Picture of Nicotine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H14N2
Nicotine
TZYWCYJVHRLUCT-VABKMULXSA-N
Synonyms:
(-)-nicotine, (S)-nicotine, L-nicotine

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
(S)-nicotine + NADPH + O2 = (S)-nicotine N1-oxide + NADP+ + H2O
show the reaction diagram
-
UDP-D-glucuronate + nicotine = UDP + ?
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
nicotine + NADPH + H+ + O2 = nicotine N-oxide + NADP+ + H2O
show the reaction diagram
-
(S)-nicotine + NADPH + O2 = ?
show the reaction diagram
-
(S)-nicotine + H2O + O2 = N-methylmyosmine + H2O2
show the reaction diagram
-
UDP-D-glucuronate + nicotine = UDP + ?
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
treatment with 0.01 mM nicotine activates 5-lipoxygenase gastric cancer cell lines from 36-72 h
-
stimulates isozyme type II
-
0.5 mg/kg, 11.8% enhancement of enzymatic activity in brain
-
slightly activating with substrate amitriptyline
-
nicotine treatment in adulthood produces an immediate increase in adenylate cyclase activity in males that disappears upon withdrawal, nicotine increases the activating effect of forskolin, especially in males, overview
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Inhibitor in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibits the enzyme from lung, testis, kidney, stomach, and brain, in concert with vitamin E the enzyme from testis brain and liver is inhibited, tissue-specific inhibition of 12.5-48%, overview, nicotine has no effect on enzyme from muscle, heart, and liver
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ability of nicotine to inhibit catalytic activity of choline oxidase used for biosensorial detection of
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0.5 mg/kg, significant inhibition of enzymatic activity in liver (61.5%), lung (65%), heart (70.5%), stomach (72.5%), kidney (64%) and testicle (71.5%)
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decreases glutamic acid decarboxylase 67 promoter methylation by DMT1 in GABAergic interneurons
-
about 16% inhibition at 0.01 mM
-
attenuates beta-amyloid peptide 1-42-induced activation of GSK-3beta
-
50% decrease in DDAH-2 mRNA
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3D Structure of Enzyme-Ligand-Complex (PDB) (16 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3
-
pH 8.5, 25°C
2.03
-
pH 7.0, 40°C

KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.13
-
pH 8.5, 25°C
0.396
-
pH 7.0, 40°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.214
-
pH 7.4, 37°C

References & Links

Links to other databases for Nicotine

ChEBI
PubChem
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PubChem