Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:08 UTC |
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Update date | 2020-09-17 15:38:35 UTC |
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Primary ID | FDB006426 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Uracil |
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Description | Uracil, also known as U or hybar X, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil is an extremely weak basic (essentially neutral) compound (based on its pKa). Uracil exists in all living species, ranging from bacteria to humans. Within humans, uracil participates in a number of enzymatic reactions. In particular, uracil and ribose 1-phosphate can be biosynthesized from uridine; which is catalyzed by the enzyme uridine phosphorylase 2. In addition, uracil can be converted into dihydrouracil through its interaction with the enzyme dihydropyrimidine dehydrogenase [nadp(+)]. In humans, uracil is involved in pyrimidine metabolism. Outside of the human body, Uracil is found, on average, in the highest concentration within beers. Uracil has also been detected, but not quantified in, several different foods, such as radish (var.), green beans, cauliflowers, prickly pears, and citrus. This could make uracil a potential biomarker for the consumption of these foods. Uracil is a potentially toxic compound. Uracil, with regard to humans, has been found to be associated with several diseases such as canavan disease, hypertension, and cerebral infarction; uracil has also been linked to several inborn metabolic disorders including carbamoyl phosphate synthetase deficiency and dihydropyrimidine dehydrogenase deficiency. |
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CAS Number | 66-22-8 |
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Structure | |
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Synonyms | Synonym | Source |
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2,4(1H,3H)-Pyrimidinedione | ChEBI | 2,4-Dioxopyrimidine | ChEBI | 2,4-Pyrimidinedione | ChEBI | U | ChEBI | Ura | ChEBI | Urazil | ChEBI | 2,4-Dihydroxypyrimidine | HMDB | 2,4-Pyrimidinediol | HMDB | Hybar X | HMDB | Pirod | HMDB | Pyrod | HMDB | 1H-Pyrimidine-2,4-dione | biospider | 2,4-dihydroxypyrimidine | biospider | 2,4(1H,3H)-Pyrimidinedione (9CI) | biospider |
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Predicted Properties | |
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Chemical Formula | C4H4N2O2 |
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IUPAC name | 1,2,3,4-tetrahydropyrimidine-2,4-dione |
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InChI Identifier | InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) |
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InChI Key | ISAKRJDGNUQOIC-UHFFFAOYSA-N |
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Isomeric SMILES | O=C1NC=CC(=O)N1 |
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Average Molecular Weight | 112.0868 |
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Monoisotopic Molecular Weight | 112.027277382 |
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Classification |
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Description | Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Diazines |
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Sub Class | Pyrimidines and pyrimidine derivatives |
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Direct Parent | Pyrimidones |
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Alternative Parents | |
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Substituents | - Pyrimidone
- Hydropyrimidine
- Heteroaromatic compound
- Vinylogous amide
- Urea
- Lactam
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen 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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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 330 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 3.6 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -1.07 | HANSCH,C ET AL. (1995) |
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Experimental pKa | 9.45 | |
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Isoelectric point | Not Available | |
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Charge | 0 | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-03xu-9400000000-d7ffe72f606f1af3349b | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-0002-5950000000-18425875415ad150c4fc | Spectrum | GC-MS | Uracil, 2 TMS, GC-MS Spectrum | splash10-006t-9740000000-e884a4b98e7e9dc75e5f | Spectrum | GC-MS | Uracil, 2 TMS, GC-MS Spectrum | splash10-052e-7790000000-026cb6beb5cde6a61b80 | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-02tc-9200000000-4a57c4e06fd552d6a9bf | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-03xu-9400000000-1c29f070a8135b06f88b | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-0002-5950000000-18425875415ad150c4fc | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-006t-9740000000-e884a4b98e7e9dc75e5f | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-052e-7790000000-026cb6beb5cde6a61b80 | Spectrum | GC-MS | Uracil, non-derivatized, GC-MS Spectrum | splash10-0002-6940000000-a726178341f6443e60cc | Spectrum | Predicted GC-MS | Uracil, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03xu-9300000000-6a96f6ce1ef731689107 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-3900000000-e422eda255a4b6414f86 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-006y-9000000000-130eb5f4414426e03667 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9100000000-c096d08ca715d97cd732 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive | splash10-02tc-9200000000-83a0a6ad4fc1b407e570 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-03xu-9400000000-acd0cfd54af7d6a55283 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-03di-0900000000-309fe212c929f3c6a930 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-03di-6900000000-55a7de75a40eab61da8b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0006-9000000000-1c3caab26eb7e359db92 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0006-9000000000-7494d4e611a73ecb79ea | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0006-9000000000-ed4046b040337db620d8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03di-0900000000-ff54f3083ce4ccccfd95 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-03di-0900000000-6728c1eb6f68b40c09f8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-0900000000-309fe212c929f3c6a930 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-03di-6900000000-55a7de75a40eab61da8b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-1c3caab26eb7e359db92 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-7494d4e611a73ecb79ea | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-9000000000-ed4046b040337db620d8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-03di-0900000000-6728c1eb6f68b40c09f8 | Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-03di-0900000000-a21102c708f8d5eaf262 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-1900000000-0029cbdcaa1377a4d03e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0229-9400000000-c227e1deb392170cb323 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-3cf6f9fc3ab6890266ac | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-4900000000-67a3d94ab649e28bda13 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9100000000-bbf50de54fc413b6588e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-98042b91f1087b0c2563 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 1141 |
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ChEMBL ID | CHEMBL566 |
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KEGG Compound ID | C00106 |
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Pubchem Compound ID | 1174 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17568 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03419 |
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HMDB ID | HMDB00300 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | URACIL |
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BIGG ID | 33879 |
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KNApSAcK ID | C00001513 |
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HET ID | URA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Uracil |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Purine nucleoside phosphorylase | PNP | P00491 | Thymidine phosphorylase | TYMP | P19971 | Uridine phosphorylase 1 | UPP1 | Q16831 | Uridine phosphorylase 2 | UPP2 | O95045 | Uridine-cytidine kinase-like 1 | UCKL1 | Q9NWZ5 | Uracil phosphoribosyltransferase homolog | UPRT | Q96BW1 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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