Ligand acetylsalicylic acid

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Basic Ligand Information

Molecular Structure
Picture of acetylsalicylic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H8O4
acetylsalicylic acid
BSYNRYMUTXBXSQ-UHFFFAOYSA-N
Synonyms:
acetyl-salicylic acid, Acetylsalicylate, Acetyl salicylate, acetyl salicylic acid, aspirin
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetylsalicylic acid + H2O = acetate + salicylate
show the reaction diagram
-
acetylsalicylic acid + H2O = acetate + salicylate
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
aspirin + NADH + O2 = ? + NAD+ + H2O + CO2
show the reaction diagram
-
acetylsalicylic acid + H2O = acetate + salicylate
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enhances activity
-
ASA, 40% activation of 15(S)-HETE production at 0.02 mM in ASA-sensitive asthmatic patients
-
maximal activation at 0.004 mM
-
induces enzyme expression in the liver and stimulates enzymatic activity in blood plasma
-

Inhibitor in Enzyme-catalyzed Reactions (42 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1 mM, 4.4% inhibition of hepatic allotype ADH1B*1/*1 activity, 2.8% inhibition of hepatic allotype ADH1B*2/*2 activity
-
IC50 for the 3 isozymes CHCR1-3, overview
-
equimolar to substrate inhibits 65% of enzyme activity
-
salicylate, non-competitive, only androsterone oxidation, pH 7.0
-
aspirin
-
a non-steroidal anti-inflammatory drug, decreases adrenaline- or dibutyryl cAMP-stimulated glycerol release in isolated adipocytes
-
binds near enough to the substrate site to prevent catalysis but does not affect dissociation of the substrate-enzyme complex
-
binds near enough to the substrate site to prevent catalysis but not affect dissociation of the substrate-enzyme complex
-
reduced activity in microsomes
-
reduced activity in microsomes
-
2 mM, 84% inhibition
-
80% inhibition at 0.2 mM
-
at 37°C, 5% slightly reduces activity by 10% concentration
-
noncompetitive inhibition of isozymes carbonic anhydrase I and II
-
blocks the STAT6-dependent interleukin-4-inducible expression of LTC4S
-

3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

KM Value (8 results)

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

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.021
-
-
0.65
-
for androsterone oxidation
0.00827
-
pH 8.5, 37°C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.2
-
;
1.52
-
IC50: 1.52 mM
1.3
-
pH 7.4, 37°C, versus 4-nitrophenol
1.5
-
pH 6.5, 37°C, versus beta-estradiol
0.008742
-
pH 8.5, 37°C

References & Links

Links to other databases for acetylsalicylic acid

ChEBI
PubChem
ChEBI
PubChem