Ligand paracetamol

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Basic Ligand Information

Molecular Structure
Picture of paracetamol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H9NO2
paracetamol
RZVAJINKPMORJF-UHFFFAOYSA-N
Synonyms:
4-acetamidophenol, 4-acetaminophen, acetaminophen, acetoaminophen, N-(4-hydroxyphenyl)acetamide, N-acetyl-4-aminophenol, N-acetyl-p-aminophenol, p-hydroxyacetanilide, tylenol

Show all pahtways known for Show all pathways known for paracetamol

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'-phosphoadenylyl sulfate + acetaminophen = adenosine 3',5'-bisphosphate + 4-(acetylamino)phenylsulfate
show the reaction diagram
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4-acetamidophenol + H2O = acetate + 4-aminophenol
show the reaction diagram

Substrate in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetaminophen + NAD(P)H + H+ = N-acetyl-p-benzoquinone imine + NAD(P)+
show the reaction diagram
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acetaminophen + UDP-glucuronate = ?
show the reaction diagram
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4-nitrophenyl sulfate + 4-acetaminophen = 4-nitrophenol + 4-acetaminophenylsulfate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetanilide + H2O2 = paracetamol + H2O
show the reaction diagram
-
-
acetyl-CoA + p-aminophenol = CoA + N-acetyl-p-aminophenol
show the reaction diagram
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acetyl-CoA + 4-aminophenol = CoA + N-acetyl-4-aminophenol
show the reaction diagram
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-
N-acetyl-4-aminophenyl N-acetyl-beta-D-glucosaminide + H2O = N-acetyl-4-aminophenol + N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.5 mM, 16% inhibition of hepatic allotype ADH1B*1/*1 activity, 6.1% inhibition of hepatic allotype ADH1B*2/*2 activity
-
non-competitive, only androsterone oxidation, pH 7.0
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no affect on holoenzyme, significant inhibition of apoenzyme, changes in brain serotonin levels due to inhibition of hepatic tryptophan 2,3-dioxygenase
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inhibits creatine kinase in cerebellum and hippocampus, the administration of N-acetylcysteine plus deferoxamine reverses the inhibition of creatine kinase activity
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at 37C, 5% slightly reduces activity by 18% concentration
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mechanism of PLD inhibition by paracetamol is noncompetitive inhibition
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competitive at 27C, uncompetitive at 37C
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treatment promotes the loss of glutamate cysteine ligase in liver. Activation of glycogen synthase kinase 3beta is a key mediator of the initial phase of acetaminophen-induced liver injury through modulating GCL and Mcl-1 degradation, as well as JNK activation in liver. The silencing of glycogen synthase kinase 3beta decreases the loss of hepatic GCL, and promotes greater GSH recovery in liver following acetaminophen treatment
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

KM Value (7 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
21.2
-
-

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
5.162
-
-
0.00923
-
at pH 7.5 and 20C

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
5.168
-
-
0.044
-
-

References & Links

Links to other databases for paracetamol

ChEBI
PubChem
ChEBI
PubChem