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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-06-26 16:21:40 UTC |
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HMDB ID | HMDB0000295 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Uridine 5'-diphosphate |
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Description | Uridine 5'-diphosphate, also known as 5'-UDP or uridine diphosphoric acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Uridine 5'-diphosphate is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. Uridine 5'-diphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-diphosphate exists in all living species, ranging from bacteria to humans. Within humans, uridine 5'-diphosphate participates in a number of enzymatic reactions. In particular, tamoxifen-N-glucuronide and uridine 5'-diphosphate can be biosynthesized from tamoxifen and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 1-4. In addition, 4-hydroxytamoxifen-O-glucuronide and uridine 5'-diphosphate can be biosynthesized from 4-hydroxytamoxifen and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 1-4. In humans, uridine 5'-diphosphate is involved in tamoxifen metabolism pathway. Outside of the human body, Uridine 5'-diphosphate has been detected, but not quantified in, several different foods, such as pineapples, pine nuts, potato, swiss chards, and lima beans. This could make uridine 5'-diphosphate a potential biomarker for the consumption of these foods. Uridine 5'-diphosphate induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). |
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Structure | |
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Synonyms | Value | Source |
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Uridine diphosphate | ChEBI | Uridine diphosphoric acid | Generator | Uridine 5'-diphosphoric acid | Generator | 5'-UDP | HMDB | UDP | HMDB | Uridine 5'-pyrophosphate | HMDB | Uridine 5'-pyrophosphorate | HMDB | Uridine 5'-pyrophosphoric acid | HMDB | Uridine pyrophosphate | HMDB | Pyrophosphate, uridine | HMDB | Diphosphate, uridine | HMDB | 5’-UDP | HMDB | Uridine 5'-(trihydrogen pyrophosphate) | HMDB | Uridine 5'-diphosphate | HMDB | Uridine 5’-(trihydrogen pyrophosphate) | HMDB | Uridine 5’-diphosphate | HMDB | Uridine 5’-diphosphoric acid | HMDB | Uridine 5’-pyrophosphate | HMDB | Uridine 5’-pyrophosphoric acid | HMDB |
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Chemical Formula | C9H14N2O12P2 |
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Average Molecular Weight | 404.1612 |
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Monoisotopic Molecular Weight | 404.002196946 |
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IUPAC Name | [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid |
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Traditional Name | UDP |
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CAS Registry Number | 58-98-0 |
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SMILES | O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O |
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InChI Identifier | InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 |
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InChI Key | XCCTYIAWTASOJW-XVFCMESISA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleotides |
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Sub Class | Pyrimidine ribonucleotides |
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Direct Parent | Pyrimidine ribonucleoside diphosphates |
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Alternative Parents | |
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Substituents | - Pyrimidine ribonucleoside diphosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Hydroxypyrimidine
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Heteroaromatic compound
- Tetrahydrofuran
- Secondary alcohol
- 1,2-diol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-4911000000-e0e7874495a5b5baf6b1 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00pi-3795210000-ef08b4deabe40209df75 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0002-9000000000-7c065a8df0e08b8c365f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0002-9000000000-73234233232c376d095c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0002-9000000000-7c065a8df0e08b8c365f | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0pdi-6910600000-bf4136774851b6559f17 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0pdi-6910600000-bf4136774851b6559f17 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-1901000000-4c9ba16543da8ee18c74 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-4901000000-1ff9973ec00da457d453 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-7900000000-f88f01d934d46a57fefb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ik9-3904300000-454bc02fb8862a1d0fac | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057l-9801000000-5aabcad933dc7e5003a8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9100000000-7a6d480c699f409f2f36 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
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Biospecimen Locations | |
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Tissue Locations | - Placenta
- Prostate
- Thyroid Gland
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 41.0 +/- 12.0 uM | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB03435 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031236 |
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KNApSAcK ID | C00007313 |
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Chemspider ID | 5809 |
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KEGG Compound ID | C00015 |
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BioCyc ID | UDP |
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BiGG ID | 33518 |
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Wikipedia Link | Uridine_Diphosphate |
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METLIN ID | Not Available |
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PubChem Compound | 6031 |
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PDB ID | Not Available |
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ChEBI ID | 17659 |
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Food Biomarker Ontology | Not Available |
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VMH ID | UDP |
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MarkerDB ID | |
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References |
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Synthesis Reference | Zeng, Bin; Rao, Linfan; Li, Gaowo. Method for manufacturing uridine diphosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 14pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Brouwer A, Morse DC, Lans MC, Schuur AG, Murk AJ, Klasson-Wehler E, Bergman A, Visser TJ: Interactions of persistent environmental organohalogens with the thyroid hormone system: mechanisms and possible consequences for animal and human health. Toxicol Ind Health. 1998 Jan-Apr;14(1-2):59-84. [PubMed:9460170 ]
- Kamisako T, Kobayashi Y, Takeuchi K, Ishihara T, Higuchi K, Tanaka Y, Gabazza EC, Adachi Y: Recent advances in bilirubin metabolism research: the molecular mechanism of hepatocyte bilirubin transport and its clinical relevance. J Gastroenterol. 2000;35(9):659-64. [PubMed:11023036 ]
- Syme MR, Paxton JW, Keelan JA: Drug transfer and metabolism by the human placenta. Clin Pharmacokinet. 2004;43(8):487-514. [PubMed:15170365 ]
- Collier AC, Tingle MD, Paxton JW, Mitchell MD, Keelan JA: Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. Hum Reprod. 2002 Oct;17(10):2564-72. [PubMed:12351530 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Morrone FB, Jacques-Silva MC, Horn AP, Bernardi A, Schwartsmann G, Rodnight R, Lenz G: Extracellular nucleotides and nucleosides induce proliferation and increase nucleoside transport in human glioma cell lines. J Neurooncol. 2003 Sep;64(3):211-8. [PubMed:14558596 ]
- Rise A: [Drugs and the fetus]. Tidsskr Nor Laegeforen. 1976 Jan 10;96(1):41-2. [PubMed:1257952 ]
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