Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000118
Name: Uridine 5'-monophosphate
Description:5'-Uridylic acid is a uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 5' position.
  • 5'-UMP
  • 5'-Uridylate (8CI)(9CI)
  • 5'-Uridylic acid (8CI)(9CI)
  • U
  • UMP
  • Uridine 5'-monophosphate
  • Uridine 5'-monophosphoric acid
  • Uridine 5'-phosphate
  • Uridine 5'-phosphorate
  • Uridine 5'-phosphoric acid
  • Uridine mono(dihydrogen phosphate)
  • Uridine mono(dihydrogen phosphoric acid)
  • Uridine monophosphate
  • Uridine monophosphoric acid
  • Uridine phosphate
  • Uridine phosphoric acid
  • Uridine-5'-monophosphate
  • Uridine-5'-monophosphoric acid
  • Uridine-monophosphate
  • Uridine-monophosphoric acid
  • Uridine-phosphate
  • Uridine-phosphoric acid
  • Uridylate
  • Uridylic acid
Chemical Formula: C9H13N2O9P
Average Molecular Weight: 324.1813
Monoisotopic Molecular Weight: 324.035866536
CAS number: 58-97-9
IUPAC Name:{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: uridylate
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct Parent Pyrimidine ribonucleoside monophosphates
Alternative Parents
  • Pyrimidine ribonucleoside monophosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility12.0 mg/mLALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.86 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.44 m3·mol-1ChemAxon
Polarizability26.3 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Water + Uridine 5'-monophosphate > Phosphate + Uridine
Adenosine triphosphate + Uridine 5'-monophosphate <> ADP + Uridine 5'-diphosphate
Undecaprenyl phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine > Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-monophosphate
Water + Uridine diphosphate-N-acetylglucosamine > N-Acetyl-glucosamine 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Water + Uridine diphosphategalactose > Galactose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Water + Uridine diphosphate glucuronic acid > D-Glucuronate 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Water + UDP-Glucose > Glucose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Water + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <>2 Hydrogen ion + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + Uridine 5'-monophosphate
Hydrogen ion + Orotidylic acid <> Carbon dioxide + Uridine 5'-monophosphate
Guanosine triphosphate + Uridine > Guanosine diphosphate + Hydrogen ion + Uridine 5'-monophosphate
Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate
Water + Uridine triphosphate > Hydrogen ion + Pyrophosphate + Uridine 5'-monophosphate
Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate
UDP-Glucose + Water <> Uridine 5'-monophosphate + Glucose 1-phosphate
Uridine triphosphate + Water <> Uridine 5'-monophosphate + Pyrophosphate
Adenosine triphosphate + Uridine <> ADP + Uridine 5'-monophosphate
Orotidylic acid <> Uridine 5'-monophosphate + Carbon dioxide
Uridine triphosphate + Uridine <> Uridine 5'-diphosphate + Uridine 5'-monophosphate
Guanosine triphosphate + Uridine <> Guanosine diphosphate + Uridine 5'-monophosphate
Inosine triphosphate + Uridine <> IDP + Uridine 5'-monophosphate
dATP + Uridine <> dADP + Uridine 5'-monophosphate
dGTP + Uridine <> dGDP + Uridine 5'-monophosphate
Thymidine 5'-triphosphate + Uridine <> dTDP + Uridine 5'-monophosphate
dCTP + Uridine <> dCDP + Uridine 5'-monophosphate
Deoxyuridine triphosphate + Uridine <> dUDP + Uridine 5'-monophosphate
UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + Water <> Uridine 5'-monophosphate + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
Uridine diphosphate-N-acetylglucosamine + Di-trans,poly-cis-undecaprenyl phosphate <> N-Acetyl-D-glucosaminyldiphosphoundecaprenol + Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol
Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine 5'-monophosphate
Uridine 5'-diphosphate + Water > Phosphate + Uridine 5'-monophosphate + Hydrogen ion
a UDP-sugar + Water > Uridine 5'-monophosphate + an &alpha;-D-aldose-1-phosphate + Hydrogen ion
UDP-sugar + Water > Uridine 5'-monophosphate + alpha-D-aldose 1-phosphate
Adenosine triphosphate + dCMP + Uridine 5'-monophosphate <> ADP + dCDP + Uridine 5'-diphosphate
UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol
UDP-sugar + Water <> Uridine 5'-monophosphate + alpha-D-Aldose 1-phosphate
UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate
UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + di-trans,octa-cis-undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
Uridine 5'-monophosphate + Adenosine triphosphate > Adenosine diphosphate + Uridine 5'-diphosphate + ADP + Uridine 5'-diphosphate
di-trans,octa-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine > Uridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol

Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-2953000000-f54596d9a11bbe82adc5View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03fr-0194000000-c8bedd9fabaccee15ef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0910000000-da7fb1ddd74c36aec368View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-b2c9787a3d982ecb858eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9102000000-f8b96709e62e0857c40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
  • Chiang EP, Bagley PJ, Roubenoff R, Nadeau M, Selhub J: Plasma pyridoxal 5'-phosphate concentration is correlated with functional vitamin B-6 indices in patients with rheumatoid arthritis and marginal vitamin B-6 status. J Nutr. 2003 Apr;133(4):1056-9. Pubmed: 12672918
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Munoz-Hoyos A, Molina-Carballo A, Macias M, Rodriguez-Cabezas T, Martin-Medina E, Narbona-Lopez E, Valenzuela-Ruiz A, Acuna-Castroviejo D: Comparison between tryptophan methoxyindole and kynurenine metabolic pathways in normal and preterm neonates and in neonates with acute fetal distress. Eur J Endocrinol. 1998 Jul;139(1):89-95. Pubmed: 9703384
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Wang Xing; Wang Xiuwen; Yin Mengxin; Xiao Zijun; Ma Cuiqing; Lin Zhixin; Wang Peng George; Xu Ping Production of uridine 5'-monophosphate by Corynebacterium ammoniagenes ATCC 6872 using a statistically improved biocatalytic process. Applied microbiolo
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID6030
Kegg IDC00105
ChemSpider ID5808
WikipediaUridine 5'-monophosphate
Ligand ExpoU5P


General function:
Involved in catalytic activity
Specific function:
Catalyzes the decarboxylation of orotidine 5'- monophosphate (OMP) to uridine 5'-monophosphate (UMP)
Gene Name:
Locus Tag:
Molecular weight:
24.4 kDa
Orotidine 5'-phosphate = UMP + CO(2).
General function:
Involved in cytidylate kinase activity
Specific function:
ATP, dATP, and GTP are equally effective as phosphate donors. CMP and dCMP are the best phosphate acceptors
Gene Name:
Locus Tag:
Molecular weight:
24.6 kDa
ATP + (d)CMP = ADP + (d)CDP.
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
First step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan
Gene Name:
Locus Tag:
Molecular weight:
39.7 kDa
UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Catalyzes the reversible phosphorylation of UMP to UDP, with ATP as the most efficient phosphate donor
Gene Name:
Locus Tag:
Molecular weight:
26.3 kDa
General function:
Involved in hydrolase activity
Specific function:
Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of Pseudomonas aeruginosa in stationary growth phase
Gene Name:
Locus Tag:
Molecular weight:
26.4 kDa
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
(Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate.
General function:
Involved in nucleoside metabolic process
Specific function:
Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
Gene Name:
Locus Tag:
Molecular weight:
22.9 kDa
UMP + diphosphate = uracil + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
Locus Tag:
Molecular weight:
38 kDa
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
Locus Tag:
Molecular weight:
31.2 kDa
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
Gene Name:
Locus Tag:
Molecular weight:
21.2 kDa
A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate.