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BRENDA support

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
Molfile
C9H13N2O9P
uridine 5'-monophosphate
DJJCXFVJDGTHFX-XVFCMESISA-N
 Download
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

Related pathways

Pathway Source
Pathways
BRENDA
dolichyl-diphosphooligosaccharide biosynthesis, lipid A biosynthesis, peptidoglycan biosynthesis, pyrimidine metabolism, teichoic acid biosynthesis
KEGG
Biosynthesis of cofactors, Nucleotide metabolism, Pyrimidine metabolism
MetaCyc
2-acetamido-4-amino-2,4,6-trideoxy-alpha-D-galactosyl-diphospho-ditrans,octacis-undecaprenol biosynthesis, acetan biosynthesis, Brucella abortus O antigen biosynthesis, colanic acid (Escherichia coli K12) biosynthesis, enterobacterial common 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 (19 results)

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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
-
ATP + UMP = ADP + UDP
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
-
ATP + UMP = ADP + UDP
show the reaction diagram
-
UMP + H2O = uridine + phosphate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (76 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + uridine = ADP + UMP
show the reaction diagram
-
UDP-N-acetyl-alpha-D-glucosamine + dolichyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphosphodolichol
show the reaction diagram
-
-
UDP-galactose + UDP-N-acetyl-D-glucosamine = UMP + UDP-N-acetyl-6-(D-galactose-1-phospho)-D-glucosamine
show the reaction diagram
-
UDP-glucose + ditrans,octacis-undecaprenyl phosphate = UMP + alpha-D-glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
show the reaction diagram
-
-
UDP-N-acetyl-alpha-D-glucosamine + trans,octacis-decaprenyl phosphate = UMP + N-acetyl-alpha-D-glucosaminyl-diphospho-trans,octacis-decaprenol
show the reaction diagram
-
-
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
-
-
UDP + H2O = UMP + phosphate
show the reaction diagram
-
-
UDP + H2O = UMP + phosphate
show the reaction diagram
-
-
UDP-glucose + H2O = UMP + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (69 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UMP + 2-oxoglutarate + O2 = 5'-dehydrouridine + succinate + CO2 + phosphate
show the reaction diagram
-
UMP + reduced thioredoxin = dUMP + oxidized thioredoxin + H2O
show the reaction diagram
-
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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UMP + [phosphate]n = UDP + [phosphate]n-1
show the reaction diagram
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ATP + UMP = ADP + UDP
show the reaction diagram
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
-
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
-

Product in Enzyme-catalyzed Reactions (271 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-N-acetyl-alpha-D-glucosamine + H2O = N-acetyl-D-glucosamine 1-phosphate + UMP
show the reaction diagram
-
-
AMP + uridine = adenosine + uridine 5'-phosphate
show the reaction diagram
-
-
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 + 2 H2O = UMP + 2 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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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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UTP + H2O = UMP + diphosphate
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
210052, -
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UTP + H2O = UMP + diphosphate
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)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
-

Activator in Enzyme-catalyzed Reactions (10 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
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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, 30°C, 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 (396 results)

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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
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, 30°C, pH 7.5, 58% remaining activity with glycogen synthase D as substrate and 16% with phosphorylase a
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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 inhibitor
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competitive with respect to L-Gln
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at 0.025 mM, more than 50% decrease in activity for wild-type
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weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (725 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (34 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.27
-
at pH 7.5 and 30°C
10.5
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pH 7.5, 85°C
0.0015
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reverse reaction
67
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pH 5.5, phosphohydrolase activity

KM Value (180 results)

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

Ki Value (63 results)

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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 37°C
0.23
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mutant enzyme C217S, in 50 mM Tris (pH 7.5), at 37°C
0.096
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wild-type, pH 6.8, 37°C
6.5
-
-
0.015
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competitive versus uracil
0.25
-
-
0.3107
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pH 8.5, 37°C
1.873
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pH 7.6, 37°C
4
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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)

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

References & Links

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Links to other databases for uridine 5'-monophosphate

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EXTERNAL LINKS
ChEBI
PubChem
UniChem