| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:16 -0700 |
| HMDB ID |
HMDB00296 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Uridine |
| Description |
Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a b-N1-glycosidic bond. (Wikipedia). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-b-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione
- 1-b-D-Ribofuranosyluracil
- 1-beta-delta-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione
- 1-beta-delta-Ribofuranosyluracil
- b-D-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1
- b-Uridine
- beta-delta-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1
- beta-Uridine
- Uridin
|
| Chemical Formula |
C9H12N2O6 |
| Average Molecular Weight |
244.2014 |
| Monoisotopic Molecular Weight |
244.069536126 |
| IUPAC Name |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione |
| Traditional IUPAC Name |
uridine |
| CAS Registry Number |
58-96-8 |
| 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 Key |
DRTQHJPVMGBUCF-XVFCMESISA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Pyrimidine Nucleosides and Analogues |
| Sub Class |
N/A |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- a pyrimidine ribonucleoside(Cyc)
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| Substituents |
- 1,2 Diol
- Glycosyl Compound
- Hydropyrimidine
- N Glycosyl Compound
- Oxolane
- Pentose Monosaccharide
- Primary Alcohol
- Pyrimidine
- Pyrimidone
- Saccharide
- Secondary Alcohol
|
| Direct Parent |
Pyrimidine Nucleosides and Analogues |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Component of Pyrimidine metabolism
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| Application |
Not Available |
| Cellular locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
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| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
163 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
-1.98 |
HANSCH,C ET AL. (1995) |
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| Predicted Properties |
|
| Spectra |
|
| 13C NMR Spectrum |
| 1H NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| [1H,1H] 2D NMR Spectrum |
| [1H,13C] 2D NMR Spectrum |
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| Biological Properties |
| Cellular Locations |
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
Not Available
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
3.10 (2.90-3.30) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
3.12 +/- 1.31 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.22 +/- 0.07 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.21 +/- 0.08 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.21 +/- 0.09 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.994 (0.637-1.351) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
7.7 +/- 0.9 uM |
Adult (>18 years old) |
Both |
Lesch-Nyhan syndrome |
Not Available |
| Blood |
Detected and Quantified |
|
4.23 +/- 1.92 uM |
Adult (>18 years old) |
Both |
Canavan disease |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
2.30 (1.90-2.70) uM |
Adult (>18 years old) |
Both |
Degenerative disc disease |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Degenerative disc disease |
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7.
Pubmed: 6656991
|
| Lesch-Nyhan syndrome |
- Harkness RA, McCreanor GM, Watts RW: Lesch-Nyhan syndrome and its pathogenesis: purine concentrations in plasma and urine with metabolite profiles in CSF. J Inherit Metab Dis. 1988;11(3):239-52.
Pubmed: 3148065
|
| Canavan disease |
- Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1.
Pubmed: 16139832
|
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| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB02745  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB007411 |
| KNApSAcK ID |
C00019674  |
| Chemspider ID |
5807  |
| KEGG Compound ID |
C00299  |
| BioCyc ID |
URIDINE  |
| BiGG ID |
34541  |
| Wikipedia Link |
Uridine  |
| NuGOwiki Link |
HMDB00296  |
| Metagene Link |
HMDB00296  |
| METLIN ID |
90  |
| PubChem Compound |
6029  |
| PDB ID |
URI  |
| ChEBI ID |
16704  |
| References |
| Synthesis Reference |
Doi, Muneharu; Asahi, Satoru; Izawa, Motoo. Fermentative production of uridine and cytidine. Baiosaiensu to Indasutori (1993), 51(12), 972-6. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7.
Pubmed: 15116424
- Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7.
Pubmed: 6656991
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| Enzymes |
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| Name: |
AID
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| Reactions: |
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| Gene Name: |
AID |
| Uniprot ID: |
Q546Y9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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