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Record Information
Version1.0
Creation Date2016-07-13 19:42:57 UTC
Update Date2016-07-20 20:56:43 UTC
LmdbLMDB00127
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine 5'-monophosphate
DescriptionUridine 5'-monophosphate, also known as uridylic acid or uridylate, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Uridine 5'-monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-monophosphate exists in all living species, ranging from bacteria to humans. Within humans, uridine 5'-monophosphate participates in a number of enzymatic reactions. In particular, uridine 5'-monophosphate can be converted into uridine 5'-diphosphate; which is catalyzed by the enzyme UMP-CMP kinase. In addition, uridine 5'-monophosphate can be biosynthesized from uridine 5'-diphosphate; which is catalyzed by the enzyme soluble calcium-activated nucleotidase 1. In humans, uridine 5'-monophosphate is involved in the metabolic disorder called the glut-1 deficiency syndrome pathway. Outside of the human body, Uridine 5'-monophosphate has been detected, but not quantified in, several different foods, such as naranjilla, cereals and cereal products, swedes, jicama, and chives. This could make uridine 5'-monophosphate a potential biomarker for the consumption of these foods. A pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase.
Structure
Thumb
Synonyms
ValueSource
5'-UMPChEBI
5'Uridylic acidChEBI
pUChEBI
UMPChEBI
Uridine 5'-(dihydrogen phosphate)ChEBI
Uridine 5'-phosphateChEBI
Uridine 5'-phosphoric acidChEBI
Uridine monophosphateChEBI
URIDINE-5'-monophosphATEChEBI
UridylateChEBI
Uridylic acidChEBI
5'UridylateGenerator
Uridine 5'-(dihydrogen phosphoric acid)Generator
Uridine monophosphoric acidGenerator
URIDINE-5'-monophosphoric acidGenerator
Uridine 5'-monophosphoric acidGenerator
Uridine 5'-phosphorateHMDB
Uridine mono(dihydrogen phosphate)HMDB
Uridine phosphateHMDB
Acids, uridylicHMDB
monoPhosphate, uridineHMDB
5'-monoPhosphate, uridineHMDB
Uridylic acidsHMDB
Acid, uridylicHMDB
Uridine 5' monophosphateHMDB
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 Nameuridine monophosphate
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
Description 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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-2953000000-f54596d9a11bbe82adc5Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2953000000-f54596d9a11bbe82adc5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9611000000-d241a590ba092a9137caSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fza-5933100000-760b9e44040ca55554b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03fr-0194000000-c8bedd9fabaccee15ef6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0910000000-da7fb1ddd74c36aec368Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-b2c9787a3d982ecb858eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9102000000-f8b96709e62e0857c40aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9102000000-f8b96709e62e0857c40aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-05bb-9632000000-b8ba3967a5a4fa269881Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9400000000-3d07e2fe57474fcd3e4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-5039000000-c23fa9bbd6fcb5cf53d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9111000000-5b5b7e0858807d74c34aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00os-9700000000-963e2c76c3f98512da72Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-01r2-9510000000-b934a101047c97c33c7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-3019000000-1bc3f90d1e162da0bc3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9211000000-5a9399a9558a148f349eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9111000000-47125abb177da73df355Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-c462cab8b32dc6c50361Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9010000000-f3876f614e314a89ace6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-ef91704ffebfee64c252Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004j-9100000000-585ad2bb25aaaee5854cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-60d486fec926bde90d2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1911000000-7963cbf4b5fd08b83e4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-404805c9de28466c7072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5522394ff370886e5a5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-8934000000-b1f27b01000758ca974dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-c3e61932dae0623d3924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4db5b2019eff03b12956Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB03685
HMDB IDHMDB0000288
FooDB IDFDB031248
Phenol Explorer IDNot Available
KNApSAcK IDC00007311
BiGG ID33873
BioCyc IDUMP
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkUridine_monophosphate
Chemspider ID5808
ChEBI ID16695
PubChem Compound ID6030
Kegg Compound IDC00105
YMDB IDYMDB00049
ECMDB IDECMDB00288
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available