Ligand Caffeine

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Basic Ligand Information

Molecular Structure
Picture of Caffeine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H10N4O2
Caffeine
XUYPXLNMDZIRQH-LURJTMIESA-N
Synonyms:
1,3,7-Trimethylxanthine, 2,6-dioxo-1,3,7-trimethylpurine


Show all pahtways known for Show all BRENDA pathways known for Caffeine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
caffeine + ubiquinone + H2O = 1,3,7-trimethylurate + ubiquinol
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (15 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
caffeine + O2 + NADH + H+ = paraxanthine + NAD+ + H2O + formaldehyde
show the reaction diagram
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ATP + H2O + caffeine/in = ADP + phosphate + caffeine/out
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + H2O + caffeine/in = ADP + phosphate + caffeine/out
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, activity of both isoenzymes is modestly enhanced
-
increase in enzyme activity by 4% for non-failing, 11% for idiopathic and 10% ischemic cardiomyopathic hearts
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Inhibitor in Enzyme-catalyzed Reactions (76 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
-
i.e. caffeine, slight
-
10-50 mM
-
might inhibit the enzyme
-
21% inhibition at 0.1 mM
-
6.5 mM, 18% inhibition
-
uncompetitive inhibition
-
weak competitive inhibitor
-
25% inhibition at 3 mM
-
inhibits cAMP accumulation by ACB and ACG. None among ACA, ACB and ACG is a direct target for the inhibitory effects of caffeine
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3D Structure of Enzyme-Ligand-Complex (PDB) (146 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.17
-
pH and temperature not specified in the publication
3.17
-
pH 7.5, 30°C
0.0038
-
pH 7.5, 30°C
0.167
-
pH 7.5, 35°C

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.037
-
pH and temperature not specified in the publication
0.037
-
pH 7.5, 30°C
0.042
-
pH 7.5, 30°C
0.0037
-
pH 7.5, 35°C

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.5
-
apparent Ki value
0.022
-
MAO-B
7.5
-
pH 7.8, 37°C
17.4
-
pH 9.8, 25°C
0.0102
-
in 25 mM Tris-HCl, 137 mM NaCl, 2.7 mM KCl, at pH 7.4 and 25°C

IC50 Value (14 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2.5
-
-
1.4
-
IC50: 1.4 mM
19
-
particulate enzyme
0.00824
-
pH 7.4, 25°C, versus 4-nitrophenylacetate as substrate

References & Links

Links to other databases for Caffeine

ChEBI
PubChem
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PubChem