Ligand 5-fluorouracil

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Basic Ligand Information

Molecular Structure
Picture of 5-fluorouracil (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C4H3FN2O2
5-fluorouracil
WXGMACVQSZVIDO-UHFFFAOYSA-N
Synonyms:
5-fluoro-uracil, 5-fluoropyrimidine-2,4(1H,3H)-dione, 5-fluoropyrimidine-2,4-dione, 5-fluorouracil[side 1], 5-fluorouracil[side 2], 5-FU, fluorouracil
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-fluorouracil + NADPH = 5-fluoro-5,6-dihydrouracil + NADP+
show the reaction diagram
5-fluorouracil + 5-phospho-alpha-D-ribose 1-diphosphate = 5-fluorouridine 5'-phosphate + diphosphate
show the reaction diagram
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5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate = 5-fluoro-2'-deoxyuridine + phosphate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
dihydrofluorouracil + NADP+ = 5-fluorouracil + NADPH + H+
show the reaction diagram
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5-fluorocytosine + H2O = 5-fluorouracil + NH3
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-fluorouracil + NAD+ = ?
show the reaction diagram
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5-fluorouracil + 2-oxoglutarate + O2 = ? + succinate + CO2
show the reaction diagram
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5-fluorouracil + NADPH = 5-fluoro-5,6-dihydrouracil + NADP+
show the reaction diagram
5-fluorouracil + 5-phospho-alpha-D-ribose 1-diphosphate = 5-fluorouridine 5'-phosphate + diphosphate
show the reaction diagram
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2'-deoxyuridine + 5-fluorouracil = 5-fluoro-2'-deoxyuridine + uracil
show the reaction diagram
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5-fluorouracil + 2-deoxy-alpha-D-ribose 1-phosphate = 5-fluoro-2'-deoxyuridine + phosphate
show the reaction diagram
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ATP + H2O + 5-fluorouracil[side 1] = ADP + phosphate + 5-fluorouracil[side 2]
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (72 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5-fluoropyrimidine + H2O + O2 = 5-fluorouracil + H2O2
show the reaction diagram
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dihydrofluorouracil + NADP+ = 5-fluorouracil + NADPH + H+
show the reaction diagram
-
5-fluorouracil-mismatched double-stranded DNA + H2O = 5-fluorouracil + double-stranded DNA with abasic site
show the reaction diagram
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5-fluorouridine + H2O = D-ribose + 5-fluorouracil
show the reaction diagram
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5-fluorouridine + H2O = 5-fluorouracil + D-ribose
show the reaction diagram
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5-fluorocytosine + H2O = 5-fluorouracil + NH3
show the reaction diagram
-
-
5-fluorocytosine + H2O = 5-fluorouracil + NH3
show the reaction diagram
-
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ATP + H2O + 5-fluorouracil[side 1] = ADP + phosphate + 5-fluorouracil[side 2]
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (44 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
linear non-competitive inhibitor
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competitive vs. dihydrouracil
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exposure to 5-fluorouracil leads to extensive irreversible TRMT2A-tRNA crosslinking in vivo
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50% inhibition at 0.005-0.01 mM
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Investigation of the effect of combining transient siRNA-chk transfection with the anticancer drug 5-fluorouracil on cell viability and proliferation. Choline kinase down-regulation with 5-fluorouracil treatment increased cell kill in cancer cells.
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1 mM, 14% inhibition
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P388/F11782 cell enzyme, high inhibition
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FPGS overexpression significantly enhances chemosensitivity to 5-fluorouracil, FPGS inhibition decreases chemosensitivity to 5-fluorouracil
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3D Structure of Enzyme-Ligand-Complex (PDB) (102 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

KM Value (9 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.322
-
-
0.0064
-
at pH 7.5 and 25C

Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.01
-
-
0.0561
-
pH 8.0, 37C
0.025
-
-

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00031
-
FM3A/0 cell
0.013
-
pH 7.3, 37C

References & Links

Links to other databases for 5-fluorouracil

ChEBI
PubChem
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PubChem