Record Information
Version2.0
Creation Date2012-05-31 14:07:23 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04172
Identification
Name:Urea
Description:Urea is the principal end product of protein catabolism. 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.
Structure
Thumb
Synonyms:
  • Alphadrate
  • Alphadric acid
  • Aqua care
  • Aqua care HP
  • Aquacare HP
  • Aquadrate
  • Aquadric acid
  • ARF
  • B-I-k
  • Basodexan
  • Beta-I-k
  • Breathtek ubt for h-pylori
  • Bromisovalum
  • Bubber shet
  • Calmurid
  • Calmurid HC
  • Carbaderm
  • Carbamex 330mgms
  • Carbamide
  • Carbamide resin
  • Carbamimate
  • Carbamimic acid
  • Carbamimidate
  • Carbamimidic acid
  • Carbonyl diamide
  • Carbonyl diamine
  • Carbonyldiamide
  • Carbonyldiamine
  • Carmol
  • Carmol 40
  • Carmol HC
  • Caswell No. 902
  • Dermaflex 20 Urea Cream 20%
  • Dermaflex Crm 10%
  • Dermal therapy-finger care
  • Dermal therapy-hand elbow and knee cream
  • Dermal therapy-heel care
  • Elaqua XX
  • Eucerin Lotion 10% D'uree
  • Harnstoff
  • Harnstoff [german]
  • Helicosol
  • Hyanit
  • Isourea
  • Keratinamin
  • Keratinamin kowa
  • Lotion
  • Mocovina
  • Mocovina [czech]
  • Murine ear wax removal system/murine ear drops
  • Nutraplus
  • Onychomal
  • Optigen 1200
  • Panafil
  • Pastaron
  • Pastaron (TN)
  • Pastaron 10
  • Pastaron 20
  • Pastaron 20 soft
  • Pastaron soft
  • Polyurea
  • Prespersion 75 urea
  • Pseudourea
  • Pseudourea [MeSH: pseudourea]
  • Pylori-chek breath test
  • Rubinol ST 010
  • Simply botanical sensations healing hands
  • Supercel 3000
  • Superprill
  • U-cort
  • Ultra mide
  • Ultra Mide 25
  • URE
  • Urea (JP15/USP)
  • Urea ammonium nitrate solution
  • Urea ammonium nitric acid solution
  • Urea homopolymer
  • Urea perhydrate
  • Urea perhydric acid
  • Urea solution
  • Urea-13C
  • Ureacin-10 lotion
  • Ureacin-20
  • Ureacin-40 Creme
  • Ureaphil
  • Urederm Cream 10%
  • Uree 20 Cream
  • Uremol 10 Cream 10%
  • Uremol 10 Lotion 10%
  • Uremol 20 Cream 20%
  • Ureophil
  • Urepeal
  • Urepeal l
  • Urepearl
  • Urevert
  • Urisec 22% Crm
  • Urisec Lotion 12%
  • Varioform II
  • β-I-K
Chemical Formula:CH4N2O
Weight:Average: 60.0553
Monoisotopic: 60.03236276
InChI Key:XSQUKJJJFZCRTK-UHFFFAOYSA-N
InChI:InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
CAS number:57-13-6
IUPAC Name:urea
Traditional IUPAC Name:urea
SMILES:NC(N)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ureas. These are compounds containing two amine groups joined by a carbonyl (C=O) functional group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic carbonic acids and derivatives
Sub ClassUreas
Direct ParentUreas
Alternative Parents
Substituents
  • Urea
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:132 °C
Experimental Properties:
PropertyValueSource
Water Solubility:545.0 mg/mL [YALKOWSKY,SH (1989)]PhysProp
LogP:-2.11 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility412.0 mg/mLALOGPS
logP-1.8ALOGPS
logP-1.4ChemAxon
logS0.84ALOGPS
pKa (Strongest Acidic)15.73ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.11 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.14 m3·mol-1ChemAxon
Polarizability5.1 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pyrimidine metabolismPW000942 Pw000942Pw000942 greyscalePw000942 simple
arginine metabolismPW000790 Pw000790Pw000790 greyscalePw000790 simple
glycolate and glyoxylate degradationPW000827 Pw000827Pw000827 greyscalePw000827 simple
KEGG Pathways:
EcoCyc Pathways:
  • allantoin degradation to glyoxylate III PWY-5705
  • arginine degradation III (arginine decarboxylase/agmatinase pathway) PWY0-823
  • putrescine biosynthesis I PWY-40
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0900000000-234545ed5860ba077237View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0079-3900000000-0ef80e5f5cd9dd6bd213View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-03di-9000000000-400d59bf59b857bd7c06View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-02tc-9000000000-d69da17ffbb84fb6bdcaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0900000000-234545ed5860ba077237View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0079-3900000000-0ef80e5f5cd9dd6bd213View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-1900000000-d805e3019d86aaf9fec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-8f09c5d6f5e002dfa52eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03dl-9000000000-3d983e9f9115869f55c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-9404d66c59d266164c23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-9000000000-828ab6c68e3a46ccbd88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-4bdf0d3bd74007ba840aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-7184b34bac3a316d9feaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-37fd015e8c20febde95aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-2fc4ec950c571662bb31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-3443c9c73d9a3f03e398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-11d83d6bda76c25ec73fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-02tc-9000000000-871569893ccfa5dd5395View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
References
References:
  • 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
  • Final report of the safety assessment of Urea. Int J Toxicol. 2005;24 Suppl 3:1-56. Pubmed: 16422263
  • 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
  • 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
  • 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
  • Hobbs JR: Monitoring myelomatosis. Arch Intern Med. 1975 Jan;135(1):125-30. Pubmed: 1111461
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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. Pubmed: 19212411
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Vaidya VS, Bonventre JV: Mechanistic biomarkers for cytotoxic acute kidney injury. Expert Opin Drug Metab Toxicol. 2006 Oct;2(5):697-713. Pubmed: 17014390
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • 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
  • 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
Synthesis Reference:Leuthardt, F.; Glasson, B. Biological synthesis of urea. Verhandl. Ver. schweiz. Physiol. (1942), 21 25-7.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16199
HMDB IDHMDB00294
Pubchem Compound ID1176
Kegg IDC00086
ChemSpider ID1143
WikipediaUrea
BioCyc IDUREA
EcoCyc IDUREA
Ligand ExpoURE

Enzymes

General function:
Involved in agmatinase activity
Specific function:
Catalyzes the formation of putrescine from agmatine
Gene Name:
speB
Uniprot ID:
P60651
Molecular weight:
33557
Reactions
Agmatine + H(2)O = putrescine + urea.
General function:
Involved in ureidoglycolate hydrolase activity
Specific function:
Involved in the anaerobic utilization of allantoin. Reinforces the induction of genes involved in the degradation of allantoin and glyoxylate by producing glyoxylate
Gene Name:
allA
Uniprot ID:
P77731
Molecular weight:
18169
Reactions
(S)-ureidoglycolate + H(2)O = glyoxylate + 2 NH(3) + CO(2).

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Transporter of glycerol across the cytoplasmic membrane, with limited permeability to water and small uncharged compounds such as polyols
Gene Name:
glpF
Uniprot ID:
P0AER0
Molecular weight:
29780
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368