Ligand 6-Mercaptopurine

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Basic Ligand Information

Molecular Structure
Picture of 6-Mercaptopurine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H4N4S
6-Mercaptopurine
GLVAUDGFNGKCSF-UHFFFAOYSA-N
Synonyms:
6-mercatopurine, 6-Thiopurine, 6mercaptopurine, a thiopurine, Mercaptopurine, thiopurine
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

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
6-mercaptopurine-2'-deoxyriboside + phosphate = 6-mercaptopurine + 2-deoxy-alpha-D-ribose 1-phosphate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
6-mercaptopurine + methyl viologen + H2O = ? + reduced methyl viologen
show the reaction diagram
6-mercaptopurine + H2O + O2 = ?
show the reaction diagram
-
6-thiopurine + S-adenosyl-L-methionine = S-methyl-6-thiopurine + S-adenosyl-L-homocysteine
show the reaction diagram
-
6-mercaptopurine + 5-phospho-alpha-D-ribose 1-diphosphate = 6-mercaptopurine ribotide + diphosphate
show the reaction diagram
-
6-mercaptopurine/in + ATP + H2O = 6-mercaptopurine/out + ADP + phosphate
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glutathione + azathioprine = 6-mercaptopurine + ?
show the reaction diagram
-
-
6-mercaptopurine ribonucleoside + H2O = 6-mercaptopurine + ribose
show the reaction diagram
-
-
6-mercaptopurine riboside + H2O = 6-mercaptopurine + D-ribose
show the reaction diagram
-
6-mercaptopurine ribonucleoside + H2O = 6-mercaptopurine + D-ribose
show the reaction diagram
-
6-mercaptopurine/in + ATP + H2O = 6-mercaptopurine/out + ADP + phosphate
show the reaction diagram
-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
90% inhibition of hypoxanthine-NADP+-activity at 1 mM
competitive
-
competitive to hypoxanthine
-
10 mM, 40.1% inhibition
-
weak
-

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

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.13
-
25°C

KM Value (27 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.002
-
25°C
0.0062
-
-

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.073
-
-
0.006
-
-
0.7
-
-
0.015
-
pH 7.4, 30°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for 6-Mercaptopurine

ChEBI
PubChem
ChEBI
PubChem