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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-03-28 16:59:48 UTC
HMDB IDHMDB0000288
Secondary Accession Numbers
  • HMDB00288
Metabolite Identification
Common NameUridine 5'-monophosphate
Description5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position. Uridine 5'-monophosphate is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
5'-UMPChEBI
5'Uridylic acidChEBI
pUChEBI
Uridine 5'-(dihydrogen phosphate)ChEBI
Uridine 5'-phosphateChEBI
Uridine 5'-phosphoric acidChEBI
Uridine monophosphateChEBI
URIDINE-5'-monophosphATEChEBI
UridylateChEBI
Uridylic acidChEBI
Uridine 5'-monophosphoric acidGenerator
5'UridylateGenerator
Uridine 5'-(dihydrogen phosphoric acid)Generator
Uridine monophosphoric acidGenerator
URIDINE-5'-monophosphoric acidGenerator
UMPHMDB
Uridine 5'-phosphorateHMDB
Uridine mono(dihydrogen phosphate)HMDB
Uridine phosphateHMDB
Acids, uridylicMeSH
Monophosphate, uridineMeSH
5'-Monophosphate, uridineMeSH
Uridylic acidsMeSH
Acid, uridylicMeSH
Uridine 5' monophosphateMeSH
Chemical FormulaC9H13N2O9P
Average Molecular Weight324.1813
Monoisotopic Molecular Weight324.035866536
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 Nameuridylate
CAS Registry Number58-97-9
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
InChI KeyDJJCXFVJDGTHFX-XVFCMESISA-N
Chemical 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • 1,2-diol
  • Urea
  • Secondary alcohol
  • Lactam
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12 g/LALOGPS
logP-1.8ALOGPS
logP-2.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.44 m³·mol⁻¹ChemAxon
Polarizability26.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-2953000000-f54596d9a11bbe82adc5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2953000000-f54596d9a11bbe82adc5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9611000000-d241a590ba092a9137caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fza-5933100000-760b9e44040ca55554b3View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9102000000-f8b96709e62e0857c40aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1911000000-7963cbf4b5fd08b83e4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-404805c9de28466c7072View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5522394ff370886e5a5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-8934000000-b1f27b01000758ca974dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-c3e61932dae0623d3924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4db5b2019eff03b12956View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Clarithromycin Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Clindamycin Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Clomocycline Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Congenital disorder of glycosylation CDG-IIdThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Demeclocycline Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified184.0 +/- 127.0 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.676 +/- 2.15 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.708 +/- 1.98 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified1.90 +/- 1.07 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.893 +/- 1.08 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.21 +/- 0.19 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified0.286 +/- 0.458 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.508 +/- 1.22 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.510 +/- 0.518 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Metastatic melanoma
details
SalivaDetected and Quantified1.20 +/- 0.55 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified1.61 +/- 1.18 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified2.38 +/- 3.06 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007508
KNApSAcK IDC00007311
Chemspider ID5808
KEGG Compound IDC00105
BioCyc IDUMP
BiGG ID33873
Wikipedia LinkUridine_monophosphate
METLIN IDNot Available
PubChem Compound6030
PDB IDU
ChEBI ID16695
References
Synthesis ReferenceWang 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 microbiology and biotechnology (2007), 76(2), 321-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]

Only showing the first 10 proteins. There are 31 proteins in total.

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
Reactions
Uridine 5'-diphosphate + Water → Uridine 5'-monophosphate + Phosphoric aciddetails
General function:
Involved in thymidylate kinase activity
Specific function:
May participate in dUTP and dCTP synthesis in mitochondria. Is able to phosphorylate dUMP, dCMP, CMP, UMP and monophosphates of the pyrimidine nucleoside analogs ddC, dFdC, araC, BVDU and FdUrd with ATP as phosphate donor. Efficacy is highest for dUMP followed by dCMP; CMP and UMP are poor substrates. May be involved in mtDNA depletion caused by long term treatment with ddC or other pyrimidine analogs.
Gene Name:
CMPK2
Uniprot ID:
Q5EBM0
Molecular weight:
44958.27
Reactions
Adenosine triphosphate + Uridine 5'-monophosphate → ADP + Uridine 5'-diphosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
Uridine triphosphate + Water → Uridine 5'-monophosphate + Pyrophosphatedetails
General function:
Involved in ATP binding
Specific function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Molecular weight:
59465.77
Reactions
Adenosine triphosphate + Uridine → ADP + Uridine 5'-monophosphatedetails
Uridine triphosphate + Uridine → Uridine 5'-diphosphate + Uridine 5'-monophosphatedetails
Guanosine triphosphate + Uridine → Guanosine diphosphate + Uridine 5'-monophosphatedetails
Inosine triphosphate + Uridine → IDP + Uridine 5'-monophosphatedetails
Deoxyadenosine triphosphate + Uridine → dADP + Uridine 5'-monophosphatedetails
dGTP + Uridine → dGDP + Uridine 5'-monophosphatedetails
Thymidine 5'-triphosphate + Uridine → dTDP + Uridine 5'-monophosphatedetails
dCTP + Uridine → dCDP + Uridine 5'-monophosphatedetails
Deoxyuridine triphosphate + Uridine → dUDP + Uridine 5'-monophosphatedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
Adenosine triphosphate + Uridine → ADP + Uridine 5'-monophosphatedetails
Uridine triphosphate + Uridine → Uridine 5'-diphosphate + Uridine 5'-monophosphatedetails
Guanosine triphosphate + Uridine → Guanosine diphosphate + Uridine 5'-monophosphatedetails
Inosine triphosphate + Uridine → IDP + Uridine 5'-monophosphatedetails
Deoxyadenosine triphosphate + Uridine → dADP + Uridine 5'-monophosphatedetails
dGTP + Uridine → dGDP + Uridine 5'-monophosphatedetails
Thymidine 5'-triphosphate + Uridine → dTDP + Uridine 5'-monophosphatedetails
dCTP + Uridine → dCDP + Uridine 5'-monophosphatedetails
Deoxyuridine triphosphate + Uridine → dUDP + Uridine 5'-monophosphatedetails
General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol-P-P-oligosaccharides.
Gene Name:
DPAGT1
Uniprot ID:
Q9H3H5
Molecular weight:
46089.485
Reactions
Uridine diphosphate-N-acetylglucosamine + Dolichol-20 → Uridine 5'-monophosphate + N-acetyl-D-glucosaminyl-diphosphodolicholdetails
Uridine diphosphate-N-acetylglucosamine + Dolichol-20 → Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphosphodolicholdetails
General function:
Involved in transcription factor binding
Specific function:
Catalyzes the formation of mannose 6-phosphate (M6P) markers on high mannose type oligosaccharides in the Golgi apparatus. M6P residues are required to bind to the M6P receptors (MPR), which mediate the vesicular transport of lysosomal enzymes to the endosomal/prelysosomal compartment.
Gene Name:
GNPTAB
Uniprot ID:
Q3T906
Molecular weight:
143620.765
Reactions
Uridine diphosphate-N-acetylglucosamine + lysosomal-enzyme D-mannose → Uridine 5'-monophosphate + lysosomal-enzyme N-acetyl-D-glucosaminyl-phospho-D-mannosedetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Uridine 5'-monophosphate + Water → Uridine + Phosphoric aciddetails
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Uridine 5'-monophosphate + Water → Uridine + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Uridine 5'-monophosphate + Water → Uridine + Phosphoric aciddetails

Only showing the first 10 proteins. There are 31 proteins in total.