Record Information
Version1.0
Creation Date2016-09-30 22:28:00 UTC
Update Date2020-06-04 20:49:44 UTC
BMDB IDBMDB0000296
Secondary Accession Numbers
  • BMDB00296
Metabolite Identification
Common NameUridine
DescriptionUridine, also known as beta-uridine or allo uridine, 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 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uridine exists in all living species, ranging from bacteria to humans. In cattle, uridine is involved in the metabolic pathway called lactose synthesis pathway. Uridine has been found to be associated with several diseases known as degenerative disc disease, canavan disease, and ulcerative colitis; also uridine has been linked to several inborn metabolic disorders including argininemia and lesch-nyhan syndrome.
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 and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Lysosome
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.98HANSCH,C ET AL. (1995)
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Lysosome
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Blood
  • Colostrum
  • Liver
  • Mammary Gland
  • Milk
  • Muscle
  • Placenta
  • Ruminal Fluid
  • Testis
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified344 +/- 86 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16.07 +/- 4.91 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14.690 +/- 4.730 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified31 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified27 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified28 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified30 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified73.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14.7 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified11.76 +/- 1.81 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified11.78 +/- 2.37 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified18 +/- 10 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified2-17 uMNot SpecifiedNot Specified
Normal
details
TestisDetected and Quantified156 +/- 36 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000296
DrugBank IDDB02745
Phenol Explorer Compound IDNot Available
FooDB IDFDB007411
KNApSAcK IDC00019674
Chemspider ID5807
KEGG Compound IDC00299
BioCyc IDURIDINE
BiGG ID34541
Wikipedia LinkUridine
METLIN ID90
PubChem Compound6029
PDB IDNot Available
ChEBI ID16704
References
Synthesis ReferenceDoi, Muneharu; Asahi, Satoru; Izawa, Motoo. Fermentative production of uridine and cytidine. Baiosaiensu to Indasutori (1993), 51(12), 972-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
  2. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
  3. Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. [PubMed:11242448 ]
  4. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  5. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  6. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  7. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  8. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
O46411
Molecular weight:
64841.0
Reactions
Uridine 5'-monophosphate + Water → Uridine + Hydrogen phosphatedetails
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Not Available
Gene Name:
PUSL1
Uniprot ID:
A6QP68
Molecular weight:
34022.0
General function:
Involved in cytidine deaminase activity
Specific function:
Single-stranded DNA-specific cytidine deaminase. Involved in somatic hypermutation (SHM), gene conversion, and class-switch recombination (CSR) in B-lymphocytes by deaminating C to U during transcription of Ig-variable (V) and Ig-switch (S) region DNA. Required for several crucial steps of B-cell terminal differentiation necessary for efficient antibody responses. May also play a role in the epigenetic regulation of gene expression by participating in DNA demethylation.
Gene Name:
AICDA
Uniprot ID:
Q2PT36
Molecular weight:
24052.0
General function:
Involved in pseudouridine synthase activity
Specific function:
Pseudouridylate synthase that catalyzes pseudouridylation of RNAs. Acts as a regulator of protein synthesis in embryonic stem cells by mediating pseudouridylation of RNA fragments derived from tRNAs (tRFs): pseudouridylated tRFs inhibit translation by targeting the translation initiation complex. Also catalyzes pseudouridylation of mRNAs: mediates pseudouridylation of mRNAs with the consensus sequence 5'-UGUAG-3'. In addition to mRNAs and tRNAs, binds other types of RNAs, such as snRNAs, Y RNAs and vault RNAs, suggesting that it can catalyze pseudouridylation of many RNA types.
Gene Name:
PUS7
Uniprot ID:
Q08DI8
Molecular weight:
74594.0
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Formation of pseudouridine at position 39 in the anticodon stem and loop of transfer RNAs.
Gene Name:
PUS3
Uniprot ID:
Q3SX07
Molecular weight:
55665.0
General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
UCK1
Uniprot ID:
Q0P5A4
Molecular weight:
31195.0
Reactions
Uridine + Adenosine triphosphate → Uridine 5'-monophosphate + ADPdetails
General function:
Not Available
Specific function:
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
UPP2
Uniprot ID:
Q0VCM7
Molecular weight:
35805.0
Reactions
Uridine + Hydrogen phosphate → Uracil + Ribose 1-phosphatedetails