Ligand zebularine

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Basic Ligand Information

Molecular Structure
Picture of zebularine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H12N2O5
zebularine
RPQZTTQVRYEKCR-WCTZXXKLSA-N
Synonyms:
1-(beta-D-ribofuranosyl)-2-pyrimidone, 1-beta-D-ribofuranosylpyrimidin-2(1H)-one, 2-(1H)-pyrimidinone riboside, a pyrimidine nucleoside, N-D-ribosylpyrimidine, pyrimidine nucleoside

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
pyrimidine nucleoside + phosphate = pyrimidine base + alpha-D-ribose 1-phosphate
show the reaction diagram
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pyrimidine nucleoside + phosphate = pyrimidine base + alpha-D-ribose 1-phosphate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
zebularine + H2O + O2 = uridine + H2O2
show the reaction diagram
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pyrimidine nucleoside + phosphate = pyrimidine base + alpha-D-ribose 1-phosphate
show the reaction diagram
-
pyrimidine nucleoside + phosphate = pyrimidine base + alpha-D-ribose 1-phosphate
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cytidine + H2O = 1-beta-D-ribofuranosylpyrimidin-2(1H)-one + NH3
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. zebularine, is a more stable, less cytotoxic inhibitor compared to 5-azacytidine probably due to differing stability and reversibility of the covalent bonds. The ternary complexes between the enzyme, 2-(1H)-pyrimidinone inhibitor, and the cofactor S-adenosyl-L-methionine are maintained through the formation of a reversible covalent interaction
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Enzyme Kinetic Parameters

KM Value (6 results)

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

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00095
-
pH 7.4, 37°C

References & Links

Links to other databases for zebularine

ChEBI
PubChem
ChEBI
PubChem