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Record Information
Version1.0
Creation Date2016-07-13 19:43:03 UTC
Update Date2016-07-20 21:03:28 UTC
LmdbLMDB00132
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine
DescriptionUridine, also known as beta-uridine or Urd, belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Uridine is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in the metabolic disorder called the g(m2)-gangliosidosis: variant b, tay-sachs disease pathway. Uridine, with regard to humans, has been found to be associated with several diseases such as uremia, irritable bowel syndrome, degenerative disc disease, and canavan disease; uridine has also been linked to the inborn metabolic disorder argininemia. A ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond.
Structure
Thumb
Synonyms
ValueSource
1-beta-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dioneChEBI
1-beta-D-RibofuranosyluracilChEBI
beta-UridineChEBI
uChEBI
UrdChEBI
UridinChEBI
1-b-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dioneGenerator
1-Β-D-ribofuranosylpyrimidine-2,4(1H,3H)-dioneGenerator
1-b-D-RibofuranosyluracilGenerator
1-Β-D-ribofuranosyluracilGenerator
b-UridineGenerator
Β-uridineGenerator
1-b-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedioneHMDB
1-beta-delta-Ribofuranosyl-2,4(1H,3H)-pyrimidinedioneHMDB
1-beta-delta-RibofuranosyluracilHMDB
b-D-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1HMDB
beta-delta-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1HMDB
Allo uridineHMDB
Allo-uridineHMDB
AllouridineHMDB
Chemical FormulaC9H12N2O6
Average Molecular Weight244.2014
Monoisotopic Molecular Weight244.069536126
IUPAC Name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Nameuridine
CAS Registry Number58-96-8
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
InChI KeyDRTQHJPVMGBUCF-XVFCMESISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassNot Available
Direct ParentPyrimidine nucleosides
Alternative Parents
Substituents
  • Pyrimidine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyrimidone
  • Hydropyrimidine
  • Monosaccharide
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • Lactam
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary alcohol
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • 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-2.4ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)9.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area119.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.57 m³·mol⁻¹ChemAxon
Polarizability21.81 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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00kb-1970000000-d1bfa838a4e9fa77c862Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-1960000000-a8283468b762a8520102Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-1950000000-70fdf4785544d0968f70Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9520000000-591c0bcf8f956d710367Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-066s-2970000000-36fbef6f6b10c2895df4Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1890000000-dd0569d4351a64c566c9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1970000000-d1bfa838a4e9fa77c862Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1960000000-a8283468b762a8520102Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1950000000-70fdf4785544d0968f70Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9520000000-591c0bcf8f956d710367Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066s-2970000000-36fbef6f6b10c2895df4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1890000000-dd0569d4351a64c566c9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1940000000-8b7a5ce66afa9b9bf939Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1950000000-00519445de22f955367dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9530000000-e83d5f042dbda82911cfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0g30-5935200000-88c9a24e13b0f41cbc83Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-052f-0697120000-c9fd5b8d641165d84e92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-995de18be458c48a8d2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0590000000-4d1d6aba25697dd11da8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uki-0190000000-3aea11527d0520158d77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004l-0291010000-c8f22405e9290fccc011Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0490000000-1a2f990a874bb1868249Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0090000000-c8efbe58f0df63698b2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-0090000000-7495d9b948a8e3b7b83bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0ikc-2970000000-089539e61aec5eeed279Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0w2c-0970000000-e6a764f50c4a9c460396Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0690000000-357cb54739a10dfcbd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-9000000000-995de18be458c48a8d2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0590000000-4d1d6aba25697dd11da8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uki-0190000000-3aea11527d0520158d77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0490000000-1a2f990a874bb1868249Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0090000000-d9e34a80f1a6b4481494Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0090000000-7495d9b948a8e3b7b83bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0ikc-2970000000-089539e61aec5eeed279Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-7010b37007f5c3d9ce1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-3900000000-b4639c8c89eac6158da6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-022a-9200000000-f8472930d09b32f54790Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0291000000-aebaa77a411473acb859Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-9000000000-205562662b564ebdca28Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-776595fd1c19f6ec51cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-10358e53c56bcb50ed4cSpectrum
MSMass Spectrum (Electron Ionization)splash10-08mi-9400000000-bafe048989f1a5c86d2dSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Feces
  • Meat
  • Milk
  • Synovial Fluid
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
Synovial FluidDetected but not QuantifiedNot ApplicableNot AvailableOvine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB02745
HMDB IDHMDB0000296
FooDB IDFDB007411
Phenol Explorer IDNot Available
KNApSAcK IDC00019674
BiGG ID34541
BioCyc IDURIDINE
METLIN ID90
PDB IDNot Available
Wikipedia LinkUridine
Chemspider ID5807
ChEBI ID16704
PubChem Compound ID6029
Kegg Compound IDC00299
YMDB IDYMDB00127
ECMDB IDECMDB00296
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available