| Identification |
|---|
| YMDB ID | YMDB00127 |
|---|
| Name | Uridine |
|---|
| Species | Saccharomyces cerevisiae |
|---|
| Strain | Baker's yeast |
|---|
| Description | Uridine, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine exists in all living species, ranging from bacteria to humans. |
|---|
| Structure | |
|---|
| 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
- 1-beta-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione
- 1-beta-D-Ribofuranosyluracil
- u
- Urd
- 1-b-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione
- 1-Β-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione
- 1-Β-D-ribofuranosyluracil
- Β-uridine
- Allo uridine
- Allo-uridine
- Allouridine
|
|---|
| CAS number | 58-96-8 |
|---|
| Weight | Average: 244.2014
Monoisotopic: 244.069536126 |
|---|
| InChI Key | DRTQHJPVMGBUCF-XVFCMESISA-N |
|---|
| InChI | 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 |
|---|
| 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 |
|---|
| Chemical Formula | C9H12N2O6 |
|---|
| SMILES | [H]OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=C([H])C(=O)N([H])C2=O)[C@]([H])(O[H])[C@]1([H])O[H] |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Nucleosides, nucleotides, and analogues |
|---|
| Class | Pyrimidine nucleosides |
|---|
| Sub Class | Not Available |
|---|
| Direct Parent | Pyrimidine 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 Framework | Aromatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Charge | 0 |
|---|
| Melting point | 163 °C |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Water Solubility | Not Available | PhysProp | | LogP | -1.98 [HANSCH,C ET AL. (1995)] | PhysProp |
|
|---|
| Predicted Properties | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Organoleptic Properties | Not Available |
|---|
| SMPDB Pathways | |
|---|
| KEGG Pathways | |
|---|
| SMPDB Reactions | Not Available |
|---|
| KEGG Reactions | |
|---|
| Concentrations |
|---|
| Intracellular Concentrations | Not Available |
|---|
| Extracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
|---|
| 553 ± 61 µM | hops, malted barley | anaerobic | Baker's yeast | PMID: 16448171 | | Conversion Details Here |
|
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00kb-1970000000-d1bfa838a4e9fa77c862 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-00kb-1960000000-a8283468b762a8520102 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014i-1950000000-70fdf4785544d0968f70 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-9520000000-591c0bcf8f956d710367 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-066s-2970000000-36fbef6f6b10c2895df4 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-014i-1890000000-dd0569d4351a64c566c9 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-1970000000-d1bfa838a4e9fa77c862 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-1960000000-a8283468b762a8520102 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-1950000000-70fdf4785544d0968f70 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9520000000-591c0bcf8f956d710367 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-066s-2970000000-36fbef6f6b10c2895df4 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-1890000000-dd0569d4351a64c566c9 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014j-1940000000-8b7a5ce66afa9b9bf939 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-1950000000-00519445de22f955367d | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-056u-9530000000-e83d5f042dbda82911cf | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0g30-5935200000-88c9a24e13b0f41cbc83 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0900000000-7010b37007f5c3d9ce1f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-3900000000-b4639c8c89eac6158da6 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-022a-9200000000-f8472930d09b32f54790 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014i-0291000000-aebaa77a411473acb859 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-014j-9000000000-205562662b564ebdca28 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03di-0900000000-776595fd1c19f6ec51cd | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-0900000000-10358e53c56bcb50ed4c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-0002-0971000000-f989283d2dec564a3af0 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-00kf-9000000000-c11e7bfdec0b5c7bf450 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-000i-9000000000-104e62fbffc4110779ef | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive | splash10-03di-0900000000-eaf6ff9ac3971d6f045f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-052f-0697120000-c9fd5b8d641165d84e92 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-9000000000-995de18be458c48a8d2d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0590000000-4d1d6aba25697dd11da8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0uki-0190000000-3aea11527d0520158d77 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-004l-0291010000-c8f22405e9290fccc011 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0490000000-1a2f990a874bb1868249 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-0090000000-c8efbe58f0df63698b2c | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-0090000000-7495d9b948a8e3b7b83b | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03dj-3960000000-3466ccfdf88139ddf140 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-03di-3900000000-0d08e4a7d4b8aacee6e6 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-03di-4900000000-d942ee27b3ca1d6ef94d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-03di-9700000000-594c7bb6dc6de848ff11 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-022d-9100000000-2826c4eb794745ec3148 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-03di-0910000000-617b4ec6cf749942c0cd | JSpectraViewer | MoNA | | MS | Mass Spectrum (Electron Ionization) | splash10-08mi-9400000000-bafe048989f1a5c86d2d | JSpectraViewer | MoNA | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
|
|---|
| References |
|---|
| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Magni, G., Santarelli, I., Natalini, P., Ruggieri, S., Vita, A. (1977). "Catabolite inactivation of bakers'-yeast uridine nucleosidase. Isolation and partial purification of a specific proteolytic inactivase." Eur J Biochem 75:77-82.16754
- Almeida, C., Duarte, I. F., Barros, A., Rodrigues, J., Spraul, M., Gil, A. M. (2006). "Composition of beer by 1H NMR spectroscopy: effects of brewing site and date of production." J Agric Food Chem 54:700-706.16448171
- Nakanishi, T., Sekimizu, K. (2002). "SDT1/SSM1, a multicopy suppressor of S-II null mutant, encodes a novel pyrimidine 5'-nucleotidase." J Biol Chem 277:22103-22106.11934891
- Vickers, M. F., Yao, S. Y., Baldwin, S. A., Young, J. D., Cass, C. E. (2000). "Nucleoside transporter proteins of Saccharomyces cerevisiae. Demonstration of a transporter (FUI1) with high uridine selectivity in plasma membranes and a transporter (FUN26) with broad nucleoside selectivity in intracellular membranes." J Biol Chem 275:25931-25938.10827169
|
|---|
| Synthesis Reference: | Doi, Muneharu; Asahi, Satoru; Izawa, Motoo. Fermentative production of uridine and cytidine. Baiosaiensu to Indasutori (1993), 51(12), 972-6. |
|---|
| External Links: | |
|---|
