| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2021-10-07 20:39:30 UTC |
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| NP-MRD ID | NP0000591 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Urea |
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| Description | Urea is a highly soluble organic compound formed in the liver from ammonia produced by the deamination of amino acids. It is the principal end product of protein catabolism and constitutes about one half of the total urinary solids. Urea is formed in a cyclic pathway known simply as the urea cycle. In this cycle, amino groups donated by ammonia and L-aspartate are converted to urea. Urea is essentially a waste product; it has no physiological function. It is dissolved in blood (in humans in a concentration of 2.5 - 7.5 Mmol/liter) and excreted by the kidney in the urine. In addition, a small amount of urea is excreted (along with sodium chloride and water) in human sweat. Urea is found to be associated with primary hypomagnesemia, which is an inborn error of metabolism. |
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| Structure | InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) |
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| Synonyms | | Value | Source |
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| 1728 | ChEBI | | Carbamide | ChEBI | | Carbonyldiamide | ChEBI | | e927b | ChEBI | | H2NC(O)NH2 | ChEBI | | Harnstoff | ChEBI | | Karbamid | ChEBI | | ur | ChEBI | | Uree | ChEBI | | Pastaron | Kegg | | Alphadrate | HMDB | | ARF | HMDB | | b-I-K | HMDB | | beta-I-K | HMDB | | Bromisovalum | HMDB | | Bubber shet | HMDB | | Calmurid | HMDB | | Calmurid HC | HMDB | | Carbaderm | HMDB | | Carbamide resin | HMDB | | Carbonyl diamide | HMDB | | Carbonyl diamine | HMDB | | Carbonyldiamine | HMDB | | Carmol | HMDB | | Helicosol | HMDB | | Hyanit | HMDB | | Isourea | HMDB | | Keratinamin | HMDB | | Keratinamin kowa | HMDB | | Mocovina | HMDB | | Onychomal | HMDB | | Panafil | HMDB | | URE | HMDB | | Ureaphil | HMDB | | Ureophil | HMDB | | Basodexan | HMDB |
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| Chemical Formula | CH4N2O |
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| Average Mass | 60.0553 Da |
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| Monoisotopic Mass | 60.03236 Da |
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| IUPAC Name | urea |
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| Traditional Name | urea |
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| CAS Registry Number | 57-13-6 |
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| SMILES | NC(N)=O |
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| InChI Identifier | InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4) |
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| InChI Key | XSQUKJJJFZCRTK-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-08-03 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-29 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Organic carbonic acids and derivatives |
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| Sub Class | Ureas |
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| Direct Parent | Ureas |
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| Alternative Parents | |
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| Substituents | - Urea
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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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 | 132 °C | Not Available | | Boiling Point | 196.00 to 197.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | | Water Solubility | 545 mg/mL | Not Available | | LogP | -2.11 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - 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 ]
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- Deja M, Hildebrandt B, Ahlers O, Riess H, Wust P, Gerlach H, Kerner T: Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. Chest. 2005 Aug;128(2):580-6. [PubMed:16100141 ]
- Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52. [PubMed:11237944 ]
- Georges J: Determination of ammonia and urea in urine and of urea in blood by use of an ammonia-selective electrode. Clin Chem. 1979 Nov;25(11):1888-90. [PubMed:498498 ]
- Vaidya VS, Bonventre JV: Mechanistic biomarkers for cytotoxic acute kidney injury. Expert Opin Drug Metab Toxicol. 2006 Oct;2(5):697-713. [PubMed:17014390 ]
- Nandan RK, Sivapathasundharam B, Sivakumar G: Oral manifestations and analysis of salivary and blood urea levels of patients under going haemo dialysis and kidney transplant. Indian J Dent Res. 2005 Jul-Sep;16(3):77-82. [PubMed:16454320 ]
- Zocco MA, Di Campli C, Gaspari R, Candelli M, Nista EC, Zileri Dal Verme L, Di Gioacchino G, Santoliquido A, Flore R, Tondi P, Proietti R, Pola P, Gasbarrini G, Gasbarrini A: Improvement of mitochondrial function evaluated by ketoisocaproic acid breath test in patients with HCV infection undergoing albumin dialysis. Transplant Proc. 2005 Jul-Aug;37(6):2554-6. [PubMed:16182741 ]
- Kohnle M, Pietruck F, Kribben A, Philipp T, Heemann U, Witzke O: Ezetimibe for the treatment of uncontrolled hypercholesterolemia in patients with high-dose statin therapy after renal transplantation. Am J Transplant. 2006 Jan;6(1):205-8. [PubMed:16433776 ]
- Malyszko J, Malyszko J, Wolczynski S, Mysliwiec M: Adiponectin, leptin and thyroid hormones in patients with chronic renal failure and on renal replacement therapy: are they related? Nephrol Dial Transplant. 2006 Jan;21(1):145-52. Epub 2005 Sep 2. [PubMed:16141459 ]
- Miller TR, Anderson RJ, Linas SL, Henrich WL, Berns AS, Gabow PA, Schrier RW: Urinary diagnostic indices in acute renal failure: a prospective study. Ann Intern Med. 1978 Jul;89(1):47-50. [PubMed:666184 ]
- Authors unspecified: Final report of the safety assessment of Urea. Int J Toxicol. 2005;24 Suppl 3:1-56. [PubMed:16422263 ]
- Miles L, Heubi JE, Bove KE: Hepatocyte glycogen accumulation in patients undergoing dietary management of urea cycle defects mimics storage disease. J Pediatr Gastroenterol Nutr. 2005 Apr;40(4):471-6. [PubMed:15795597 ]
- Hobbs JR: Monitoring myelomatosis. Arch Intern Med. 1975 Jan;135(1):125-30. [PubMed:1111461 ]
- Racz I, Soos G, Jakab E: [Water content of the skin following salicylic acid and urea treatment]. Hautarzt. 1989;40 Suppl 9:61-2. [PubMed:2807925 ]
- Younes H, Alphonse JC, Deteix R: [Role of dietary fibers in the nutritional management of chronic renal failure]. Nephrologie. 2004;25(7):283-5. [PubMed:15584637 ]
- Roszczenko A, Galazyn-Sidorczuk M, Brzoska MM, Moniuszko-Jakoniuk J, Zwierz K: [Select parameters of renal function in smokers in correlation with the exposure to cadmium]. Przegl Lek. 2004;61(4):348-50. [PubMed:15521599 ]
- Gowda GA, Somashekar BS, Ijare OB, Sharma A, Kapoor VK, Khetrapal CL: One-step analysis of major bile components in human bile using 1H NMR spectroscopy. Lipids. 2006 Jun;41(6):577-89. [PubMed:16981436 ]
- Kurekci AE, Atay AA, Sarici SU, Yesilkaya E, Senses Z, Okutan V, Ozcan O: Is there a relationship between childhood Helicobacter pylori infection and iron deficiency anemia? J Trop Pediatr. 2005 Jun;51(3):166-9. Epub 2005 Apr 26. [PubMed:15855306 ]
- Fostel J, Boneva R, Lloyd A: Exploration of the gene expression correlates of chronic unexplained fatigue using factor analysis. Pharmacogenomics. 2006 Apr;7(3):441-54. [PubMed:16610954 ]
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