Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:27:58 UTC |
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Update Date | 2020-06-04 21:45:44 UTC |
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BMDB ID | BMDB0000294 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Urea |
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Description | Urea, also known as ur or carbamide, 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. Urea exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Urea exists in all living species, ranging from bacteria to humans. Urea is a potentially toxic compound. Urea has been found to be associated with several diseases known as cirrhosis, tuberculous meningitis, perillyl alcohol administration for cancer treatment, and bartter syndrome, type 2, antenatal; also urea has been linked to the inborn metabolic disorders including cholesteryl ester storage disease. |
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Structure | |
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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 Molecular Weight | 60.0553 |
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Monoisotopic Molecular Weight | 60.03236276 |
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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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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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Ontology |
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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | |
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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 | Not Available | Not Available | Water Solubility | 545.0 mg/mL | Not Available | LogP | -2.11 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0900000000-234545ed5860ba077237 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0079-3900000000-0ef80e5f5cd9dd6bd213 | View in MoNA |
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GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-02tc-9000000000-d69da17ffbb84fb6bdca | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-234545ed5860ba077237 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0079-3900000000-0ef80e5f5cd9dd6bd213 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-1900000000-d805e3019d86aaf9fec0 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-9000000000-400d59bf59b857bd7c06 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-9000000000-8f09c5d6f5e002dfa52e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03dl-9000000000-3d983e9f9115869f55c8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-9404d66c59d266164c23 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-03di-9000000000-828ab6c68e3a46ccbd88 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-01ot-9000000000-91554974873c3217dc93 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 0V, Positive | splash10-03di-9000000000-9d3431eab9093f365e2b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9000000000-4bdf0d3bd74007ba840a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9000000000-7184b34bac3a316d9fea | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-37fd015e8c20febde95a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9000000000-2fc4ec950c571662bb31 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4l-9000000000-3443c9c73d9a3f03e398 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-11d83d6bda76c25ec73f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052f-9000000000-39cd266ec67397ab213f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-90726b17dc36e29c5299 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-90726b17dc36e29c5299 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ox-9000000000-95a1106bd10162ddd326 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-b759ce75f0e73d2777db | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-fd9f25340762315b4515 | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-02tc-9000000000-871569893ccfa5dd5395 | View in MoNA |
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1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, acetone+DMSO+tetramethylurea, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Epidermis
- Kidney
- Liver
- Milk
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Urine
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 1321 +/- 282 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 6510 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 2430-2890 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 732.658-3603.346 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 1145.611 +/- 449.586 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 3840-4110 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 4121-4443 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 1950-4080 uM | Not Specified | Not Specified | Normal | | details | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2331.196 - 2381.151 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5944.551 - 6144.368 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 282.72 +/- 45.21 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1117 +/- 175 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1174 +/- 115 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1115 +/- 30 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 1104 +/- 136 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4110 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4570 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5150 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6130 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6450 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6490 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6570 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6850 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6890 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 7160 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 7310 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 7480 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2250 +/- 140 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2250 +/- 300 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2460 +/- 170 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2700 +/- 120 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 2930 +/- 110 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 4329.365 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 221.68 +/- 102.60 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 389.71 +/- 57.62 uM | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 1870 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2920 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2570 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 890 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 1872 +/- 1191 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 2928 +/- 1634 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 1977 +/- 792 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 898 +/- 84 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 898.83 +/- 984.41 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Heat stress | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | Blood | Detected and Quantified | 5570 uM | Not Specified | Not Specified | Treated with bovine somatotropin | | details | Ruminal Fluid | Detected and Quantified | 2577.19 +/- 767.12 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000294 |
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DrugBank ID | DB03904 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB012174 |
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KNApSAcK ID | C00007314 |
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Chemspider ID | 1143 |
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KEGG Compound ID | C00086 |
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BioCyc ID | UREA |
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BiGG ID | 33799 |
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Wikipedia Link | Urea |
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METLIN ID | 6 |
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PubChem Compound | 1176 |
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PDB ID | Not Available |
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ChEBI ID | 16199 |
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References |
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Synthesis Reference | Leuthardt, F.; Glasson, B. Biological synthesis of urea. Verhandl. Ver. schweiz. Physiol. (1942), 21 25-7. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Korhonen M, Vanhatalo A, Huhtanen P: Evaluation of isoleucine, leucine, and valine as a second-limiting amino acid for milk production in dairy cows fed grass silage diet. J Dairy Sci. 2002 Jun;85(6):1533-45. doi: 10.3168/jds.S0022-0302(02)74223-9. [PubMed:12146486 ]
- Vanhatalo A, Kuoppala K, Ahvenjarvi S, Rinne M: Effects of feeding grass or red clover silage cut at two maturity stages in dairy cows. 1. Nitrogen metabolism and supply of amino acids. J Dairy Sci. 2009 Nov;92(11):5620-33. doi: 10.3168/jds.2009-2249. [PubMed:19841222 ]
- Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3. [PubMed:23040012 ]
- Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11. [PubMed:9718493 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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