Ligand N-acetyl-L-cysteine

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Basic Ligand Information

Molecular Structure
Picture of N-acetyl-L-cysteine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H9NO3S
N-acetyl-L-cysteine
PWKSKIMOESPYIA-BYPYZUCNSA-N
Synonyms:
acetyl-Cys, acetylcysteine, L-acetylcysteine, N-acetyl-L-Cys, N-acetylcysteine, N-alpha-acetyl-L-cysteine, Nalpha-acetyl-L-cysteine


Show all pahtways known for Show all BRENDA pathways known for N-acetyl-L-cysteine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-amino-4-hydroxybenzoate + N-acetyl-L-cysteine + O2 = grixazone B + H2O + CO2
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N-acetyl-L-cysteine + H2O = acetate + L-cysteine
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Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + N-acetylcysteine + O2 = S-(benzohydroximoyl)-N-acetyl-L-cysteine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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N-acetylcysteine + O2 = ? + H2O
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N-acetyl-L-cysteine + O2 = N,N'-diacetyl-L-cystine
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L-acetylcysteine + dehydroascorbate = N,N'-diacetyl-L-cystine + ascorbate
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N-acetyl-L-cysteine + S-adenosyl-L-methionine = N-acetyl-S-methyl-L-cysteine + S-adenosyl-L-homocysteine
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O-acetyl-L-homoserine + N-acetyl-L-Cys = S-(L-acetylamino-2-carboxyethyl)-L-homocysteine + acetate
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thiosulfate + N-acetyl-L-cysteine = ?
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N-acetylcysteine + H2O = acetate + cysteine
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Nalpha-acetyl-L-cysteine + H2O = L-cysteine + acetate
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N-acetyl-L-cysteine + H2O = acetic acid + L-cysteine
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Ile-tRNAIle + N-acetylcysteine = S-isoleucyl-N-acetylcysteine + tRNAIle
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Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-acetyl-S-(2E,6E)-farnesyl-L-cysteine + O2 + H2O = (2E,6E)-farnesal + N-acetyl-L-cysteine + H2O2
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N-acetyl-S-(2E,6E)-farnesyl-L-cysteine + O2 + H2O = (2E,6E)-farnesal + N-acetyl-L-cysteine + H2O2
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S-(1-hydroxy-2-oxopropyl)-N-acetyl-L-cysteine + H2O = N-acetyl-L-cysteine + (R)-lactate
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Activator in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
N-acetylcysteine achieves 123.4% of the rate of cyanide production of the control in the LPO/H2O2/acetonitrile system
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addition of N-acetyl-L-cysteine significantly enhances the rate of chloroacetonitrile oxidation and cyanide release by the myeloperoxidase/H2O2/Cl- system (16.3% increase at 5 mM)
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30 mM, 31.2% activity compared to activation with dithiothreitol
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enhance oxidation of dibromoacetonitrile by the hypoxanthine/xanthine oxidase/Fe system
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enhances activity
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10 mM, increases cyclin-dependent kinase 5 phosphorylation, phosphorylation of Cdk5 on tyrosine 15 by c-Abl increases kinase activity of the p35/Cdk5 complex
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a GSH inducer, increases SULT1E1 activity, but fails to affect the enzyme amount in Hep-G2 cells
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causes an increase in Vmax value and a decrease in Km value, nonessential mode of activation
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enzyme activity depends on the presence of a reducing compound to a final concentration of 0.1mM
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Inhibitor in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
35% inhibition at 10 mM
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increased activity of xanthine oxidase in cells exposed to CoCl2 and subsequent increase in reactive oxygen species derived from enzyme activity, which results in accumulation of hypoxia-inducible factor 1alpha. Blockade of enzyme activity by allopurinol, N-acetyl-L-cysteine or siRNA significantly attenuates expression of hypoxia-inducible factor 1alpha and thus the induction of genes such as erythropoietin and vascular endothelial growth factor
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5 mM N-acetylcysteine significantly reduces G3PD activation induced by both H2O2 and ferric protoporphyrin IX
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reduces production of platelet-activating factor (PAF) in H2O2-treated HUVEC cells
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inhibits phosphorylation of IkappaBalpha
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lowers dose-dependently recombinant CN1 efficiency
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decreases enzyme activity in lung carcinoma NCI-H82 cells and reduces the cell viability, overview
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competitive
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inhibition of Cys-tRNAPro formation
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

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

KM Value (14 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.4
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13
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25
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Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.2
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pH 7.4, 38°C

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
4
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in 0.2 M sodium acetate buffer pH 5.5 containing 0.15 M NaCl at 37°C
1
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recombinant enzyme

References & Links

Links to other databases for N-acetyl-L-cysteine

ChEBI
PubChem
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PubChem