Ligand uridine 5'-monophosphate

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Basic Ligand Information

Molecular Structure
Picture of uridine 5'-monophosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H13N2O9P
uridine 5'-monophosphate
DJJCXFVJDGTHFX-XVFCMESISA-N
Synonyms:
5'-UMP, 5'UMP, D-UMP, deazauridine 5'-phosphate, UMP, uridine-5'-phosphate, uridine 5'-phosphate, Uridine 5'-phosphonic, uridine monophosphate, uridine phosphate, uridylic acid
Pathway Source
Pathways
MetaCyc
2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactosyl-diphospho-ditrans,octacis-undecaprenol biosynthesis, acetan biosynthesis, beta-D-galactosaminyl-(1rarr3)-N-acetyl-alpha-D-galactosamine biosynthesis, enterobacterial common antigen biosynthesis, Escherichia coli serotype O86 O-antigen biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for uridine 5'-monophosphate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UMP + 2-oxoglutarate + O2 = 5'-dehydrouridine + succinate + CO2 + phosphate
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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UMP + H2O = uridine + phosphate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (72 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + uridine = ADP + UMP
show the reaction diagram
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UDP-N-acetyl-alpha-D-glucosamine + dolichyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphosphodolichol
show the reaction diagram
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-
UDP-galactose + UDP-N-acetyl-D-glucosamine = UMP + UDP-N-acetyl-6-(D-galactose-1-phospho)-D-glucosamine
show the reaction diagram
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UDP-glucose + ditrans,octacis-undecaprenyl phosphate = UMP + alpha-D-glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
show the reaction diagram
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UDP-N-acetyl-alpha-D-glucosamine + trans,octacis-decaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
show the reaction diagram
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UDP-N,N'-diacetylbacillosamine + tritrans,heptacis-undecaprenyl phosphate = UMP + N,N'-diacetyl-alpha-D-bacillosaminyl-diphospho-tritrans,heptacis-undecaprenol
show the reaction diagram
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UDP-N-acetyl-alpha-D-galactosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol
show the reaction diagram
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-
UTP + H2O = UMP + diphosphate
show the reaction diagram
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-
UDP + H2O = UMP + phosphate
show the reaction diagram
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-
UDP + H2O = UMP + phosphate
show the reaction diagram
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-
UDP-glucose + H2O = UMP + alpha-D-glucose 1-phosphate
show the reaction diagram
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UDP-2,3-bis((3R)-3-hydroxymyristoyl)alpha-D-glucosamine + H2O = 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate + UMP
show the reaction diagram
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UDP + H2O = UMP + phosphate + H+
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (69 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UMP + 2-oxoglutarate + O2 = 5'-dehydrouridine + succinate + CO2 + phosphate
show the reaction diagram
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UMP + reduced thioredoxin = dUMP + oxidized thioredoxin + H2O
show the reaction diagram
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5,10-methylenetetrahydrofolate + uridine 5'-phosphate = dihydrofolate + TMP
show the reaction diagram
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UMP + phosphate = uracil + alpha-D-ribose 1,5-bisphosphate
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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UMP + [phosphate]n = UDP + [phosphate]n-1
show the reaction diagram
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5'-UMP + H2O = uridine + phosphate
show the reaction diagram
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UMP + H2O = uridine + phosphate
show the reaction diagram
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5'-UMP + H2O = uridine + phosphate
show the reaction diagram
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5'-UMP + H2O = ?
show the reaction diagram
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5'-UMP + H2O = uracil + ribose 5-phosphate
show the reaction diagram
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UMP + H2O = uridine + phosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (280 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-N-acetylglucosamine + H2O = N-acetyl-D-glucosamine 1-phosphate + UMP
show the reaction diagram
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AMP + uridine = adenosine + uridine 5'-phosphate
show the reaction diagram
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-
UDP + D-glucose = UMP + D-glucose 6-phosphate
show the reaction diagram
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ATP + uridine = ADP + UMP
show the reaction diagram
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UDP + adenosine = UMP + AMP
show the reaction diagram
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-
UDP + alpha-D-ribose-1-phosphate = UMP + alpha-D-ribose 1,5-bisphosphate
show the reaction diagram
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uridine + ATP = UMP + ADP
show the reaction diagram
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-
ATP + uridine = ADP + uridine 5'-phosphate
show the reaction diagram
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UTP + D-ribose 5-phosphate = UMP + 5-phospho-alpha-D-ribose 1-diphosphate
show the reaction diagram
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UTP + thiamine = UMP + thiamine diphosphate
show the reaction diagram
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UDP-N-acetyl-alpha-D-glucosamine + dolichyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphosphodolichol
show the reaction diagram
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UDP-glucose + glycoprotein D-mannose = UMP + glycoprotein 6-(D-glucose-1-phospho)-D-mannose
show the reaction diagram
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UDP-N-acetyl-alpha-D-glucosamine + trans,octacis-decaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
show the reaction diagram
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UDP-N-acetyl-alpha-D-galactosamine + ditrans,octacis-undecaprenyl phosphate = UMP + N-acetyl-alpha-D-galactosaminyl-diphospho-ditrans,octacis-undecaprenol
show the reaction diagram
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-
UTP + H2O = UMP + phosphate
show the reaction diagram
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-
uridine 3',5'-bisphosphate + H2O = uridine 5'-phosphate + phosphate
show the reaction diagram
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-
polyuridylic acid + H2O = 5'-UMP + 5'-phosphooligonucleotides
show the reaction diagram
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cyclic 3',5'-UMP + H2O = 5'-UMP
show the reaction diagram
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CMP + H2O = UMP + NH3
show the reaction diagram
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UDP + H2O = UMP + phosphate
show the reaction diagram
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P1,P4-bis(5'-uridyl) tetraphosphate + H2O = UTP + UMP
show the reaction diagram
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uridine 5'-phosphobutyrate + H2O = butyric acid + UMP
show the reaction diagram
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UDP + H2O = UMP + phosphate
show the reaction diagram
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uridine 5'-p-nitrophenylphosphate + H2O = p-nitrophenol + UMP
show the reaction diagram
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UDP + H2O = UMP + phosphate
show the reaction diagram
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UTP + L-aspartate + tRNAAsp = UMP + diphosphate + L-aspartyl-tRNAAsp
show the reaction diagram
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UTP + acetate + CoA = UMP + diphosphate + acetyl-CoA
show the reaction diagram
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UTP + ferulate + CoA = UMP + diphosphate + feruloyl-CoA
show the reaction diagram
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UTP + 3-hydroxypropionate + CoA + NADPH = UMP + diphosphate + NADP+ + propionyl-CoA
show the reaction diagram
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UTP + acetate + citrate (pro-3S)-lyase = UMP + diphosphate + citrate(pro-3S)-lyase
show the reaction diagram
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UTP + phytanate + CoA = UMP + diphosphate + phytanoyl-CoA
show the reaction diagram
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UTP + o-succinylbenzoate + CoA = UMP + diphosphate + o-succinylbenzoyl-CoA
show the reaction diagram
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UTP + phenylacetate + CoA = UMP + diphosphate + phenylacetyl-CoA
show the reaction diagram
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3-hydroxypropanoate + UTP + coenzyme A = 3-hydroxypropanoyl-CoA + UMP + diphosphate
show the reaction diagram
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UTP + oxalate + CoA = UMP + diphosphate + oxalyl-CoA
show the reaction diagram
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UTP + (R)-pantoate + beta-alanine = UMP + diphosphate + (R)-pantothenate
show the reaction diagram
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UTP + biotin + apo-[propanoyl-CoA:carbon-dioxide ligase (ADP-forming)] = UMP + diphosphate + [propanoyl-CoA:carbon-dioxide ligase (ADP-forming)]
show the reaction diagram
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UTP + biotin + apo-[methylmalonyl-CoA:pyruvate carboxyltransferase] = UMP + diphosphate + [methylmalonyl-CoA:pyruvate carboxyltransferase]
show the reaction diagram
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UTP + L-Asp + L-Gln = UMP + diphosphate + Asn + Glu
show the reaction diagram
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UTP + RNA 3'-terminal-phosphate = UMP + diphosphate + RNA terminal-2',3'-cyclic-phosphate
show the reaction diagram
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UTP + (deoxyribonucleotide)n + (deoxyribonucleotide)m = UMP + diphosphate + (deoxyribonucleotide)n+m
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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Activator in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
-
the protein activators PII and PII-UMP binding to the enzyme domain with the opposing activity, with intramolecular signal transduction by direct interactions between the N-terminal adenylyl-removing catalytic domain and the C-terminal adenylyltransferase catalytic domain
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1.4 mM, 30C, pH 7.5, 102% relative activity with histone as substrate
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2',3'-cyclic nucleotide phosphodiesterase activity
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slight stimulation at 0.4-1 mM
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activates the reduction of epimerase-bound NAD+
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Inhibitor in Enzyme-catalyzed Reactions (372 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
25% inhibition at 0.6 mM
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5 mM, about 15% inhibition
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weak
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10 mM, 43% inhibition
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41% inhibition
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6.25 mM
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10 mM: 55% inhibition, 1 mM: 34% inhibition
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10 mM, 50% inhibition
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weak
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1 mM, 51% inhibition
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best inhibitor
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1 mM, 64% inhibition
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UMP and UDP-GalNAc are 100fold less potent than UDP, UTP, and UDP-GlcNAc
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competitive with UDP-glucose, uncompetitive with 3-phospho-D-glycerate
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in phosphorolysis, 30% inhibition at 3 mM
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competitively inhibits the transfer of galactose to glycoprotein substrates
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strong
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competitively inhibits the transfer of galactose to glycoprotein substrates
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5 mM, 25% inhibition
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xanthine and uracil pyrophosphorylase
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25% residual activity at 10 mg/ml
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weak
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very weak
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0.1 mM, 24% inhibition
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substrate inhibition above 0.2 mM
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10-15% inhibition at 5 mM
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5 mM, about 15% inhibition
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inhibits catabolic reaction
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inhibits uridylyl removing activity
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slight
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little effect
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0.04 mM: 56% inhibition, 0.1 mM: 76% inhibition, 0.4 mM: 93% inhibition
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1.4 mM, 30C, pH 7.5, 58% remaining activity with glycogen synthase D as substrate and 16% with phosphorylase a
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74.5% inhibition at 10 mM
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uncompetitive inhibitor
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slight inhibition
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slight inhibition
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0.5 mM, presence of 0.5 mM NAD+, 93% residual activity
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1 mM, 23% inhibition of purified His6-tagged RHM2-N protein is inhibited
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competitive with respect to L-Gln
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weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (60 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (37 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.27
-
at pH 7.5 and 30C
10.5
-
pH 7.5, 85C
0.0015
-
reverse reaction
67
-
pH 5.5, phosphohydrolase activity
3.33
-
synthesis of a copolymer of uridylic acid

KM Value (173 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
at pH 7.5 and 30C
4.5
-
reaction with cytochrome c
4.4
-
pH 7.5, 85C
0.13
-
-
0.09
-
pH 5.5
0.221
-
-
6.95
-
-

Ki Value (59 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.00049
-
-
0.23
-
mutant enzyme C217S, in 50 mM Tris (pH 7.5), at 37C
0.23
-
mutant enzyme C217S, in 50 mM Tris (pH 7.5), at 37C
0.096
-
wild-type, pH 6.8, 37C
6.5
-
-
0.015
-
competitive versus uracil
0.25
-
-
0.3107
-
pH 8.5, 37C
0.3345
-
at pH 7.4 and 25C; recombinant wild-type enzyme, pH 7.4, 25C
1.873
-
pH 7.6, 37C
4
-
binds to the active site of the enzyme by anchoring two molecules connected to each other by hydrogen bonds and van der Waals interactions

IC50 Value (8 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.019
-
-
4
-
at pH 7.5 and 30C
3
-
in 50 mM Tris-HCl pH 8.0, at 25C
0.4
-
-

References & Links