You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:15 UTC
HMDB IDHMDB00294
Secondary Accession NumbersNone
Metabolite Identification
Common NameUrea
DescriptionUrea 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.
Structure
Thumb
Synonyms
  1. Alphadrate
  2. ARF
  3. B-I-k
  4. beta-I-k
  5. Bromisovalum
  6. Bubber shet
  7. Calmurid
  8. Calmurid HC
  9. Carbaderm
  10. Carbamide
  11. Carbamide resin
  12. Carbonyl diamide
  13. Carbonyl diamine
  14. Carbonyldiamide
  15. Carbonyldiamine
  16. Carmol
  17. Helicosol
  18. Hyanit
  19. Isourea
  20. Keratinamin
  21. Keratinamin kowa
  22. Mocovina
  23. Onychomal
  24. Panafil
  25. URE
  26. Urea
  27. Ureaphil
  28. Ureophil
Chemical FormulaCH4N2O
Average Molecular Weight60.0553
Monoisotopic Molecular Weight60.03236276
IUPAC Nameurea
Traditional IUPAC Nameurea
CAS Registry Number57-13-6
SMILES
NC(N)=O
InChI Identifier
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
InChI KeyXSQUKJJJFZCRTK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassUreas
Sub ClassN/A
Other Descriptors
  • a small molecule(Cyc)
  • isourea(ChEBI)
Substituents
  • N/A
Direct ParentUreas
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point132 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility545.0 mg/mLNot Available
LogP-2.11HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility412 g/LALOGPS
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 area69.11ChemAxon
rotatable bond count0ChemAxon
refractivity13.14ChemAxon
polarizability5.1ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Prostate
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
Urea CycleSMP00059map00330
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6074.6 +/- 2154.2 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified4530.0 (2590.0 - 6470.0) uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4010.0 +/- 920.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified3600.0 (2680.0 - 4780.0) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified5210.0 (4310.0 - 6780.0) uMChildren (1-13 years old)Not Specified
Normal
    • Geigy Scientific ...
details
BloodDetected and Quantified6500.0 (4000.0-9000.0) uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified2960 +/- 1000 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified3820.0 (0.0-7640.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4160.0 (2300.0-6060.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
SalivaDetected and Quantified1-6985 uMAdult (>18 years old)Male
normal
details
SalivaDetected and Quantified1-9528 uMAdult (>18 years old)Male
normal
details
UrineDetected and Quantified15491.64-38812.40 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified22566.0 +/- 4407.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified6286.43 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified12285 (174-49097) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified29.6 (6.579-52.6) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified3500.0 +/- 1500.0 uMAdult (>18 years old)BothCirrhosis details
    BloodDetected and Quantified3309.9 +/- 1844 uMAdult (>18 years old)Not SpecifiedHeart Transplant details
    Cerebrospinal Fluid (CSF)Detected and Quantified1800.0 (1500.0-2100.0) uMAdult (>18 years old)BothTuberculous meningitis details
    Cerebrospinal Fluid (CSF)Detected and Quantified2150.0 (1850.0-2450.0) uMAdult (>18 years old)Both
    Meningitis
    details
    Associated Disorders and Diseases
    Disease References
    Cirrhosis
    1. Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. Pubmed: 7752905
    Meningitis
    1. 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
    Tuberculous meningitis
    1. 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
    Associated OMIM IDsNone
    DrugBank IDDB03904
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB012174
    KNApSAcK IDC00007314
    Chemspider ID1143
    KEGG Compound IDC00086
    BioCyc IDUREA
    BiGG ID33799
    Wikipedia LinkUrea
    NuGOwiki LinkHMDB00294
    Metagene LinkHMDB00294
    METLIN ID6
    PubChem Compound1176
    PDB IDURE
    ChEBI ID16199
    References
    Synthesis ReferenceLeuthardt, F.; Glasson, B. Biological synthesis of urea. Verhandl. Ver. schweiz. Physiol. (1942), 21 25-7.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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
    2. 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
    3. 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
    4. 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
    5. 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
    6. Vaidya VS, Bonventre JV: Mechanistic biomarkers for cytotoxic acute kidney injury. Expert Opin Drug Metab Toxicol. 2006 Oct;2(5):697-713. Pubmed: 17014390
    7. 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
    8. 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
    9. 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
    10. 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
    11. 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
    12. Final report of the safety assessment of Urea. Int J Toxicol. 2005;24 Suppl 3:1-56. Pubmed: 16422263
    13. 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
    14. Hobbs JR: Monitoring myelomatosis. Arch Intern Med. 1975 Jan;135(1):125-30. Pubmed: 1111461
    15. 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
    16. 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
    17. 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
    18. 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
    19. 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
    20. 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

    Enzymes

    General function:
    Involved in arginase activity
    Specific function:
    Not Available
    Gene Name:
    ARG1
    Uniprot ID:
    P05089
    Molecular weight:
    34734.655
    Reactions
    L-Arginine + Water → Ornithine + Ureadetails
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
    3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
    General function:
    Involved in arginase activity
    Specific function:
    May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders.
    Gene Name:
    ARG2
    Uniprot ID:
    P78540
    Molecular weight:
    38577.515
    Reactions
    L-Arginine + Water → Ornithine + Ureadetails
    General function:
    Involved in carbonate dehydratase activity
    Specific function:
    Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
    Gene Name:
    CA2
    Uniprot ID:
    P00918
    Molecular weight:
    29245.895
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
    General function:
    Involved in binding
    Specific function:
    Involved in signal transduction through the Wnt pathway. Nuclear beta-catenin it involved in transcriptional regulation by association with transcription factors of the TCF/LEF family
    Gene Name:
    CTNNB1
    Uniprot ID:
    P35222
    Molecular weight:
    85495.9
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
    3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
    General function:
    Involved in agmatinase activity
    Specific function:
    Not Available
    Gene Name:
    AGMAT
    Uniprot ID:
    Q9BSE5
    Molecular weight:
    37660.065
    Reactions
    Agmatine + Water → Putrescine + Ureadetails
    General function:
    Involved in G-protein coupled receptor activity
    Specific function:
    Receptor that is activated by both amino acids and extracellular concentration of calcium ions. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. Senses changes in the extracellular concentration of calcium ions, suggesting that it may mediate extracellular calcium-sensing responses in osteoblasts. Osteocalin, stimulates its activity in presence of calcium. Has a lower affinity for calcium than CASR. Also acts as a receptor for amino acids, with a preference for basic amino acids such as L-Lys, L-Arg and L-ornithine. Its affinity for amino acids suggests that it may act as a regulatory component of the urea cycle
    Gene Name:
    GPRC6A
    Uniprot ID:
    Q5T6X5
    Molecular weight:
    104752.2
    General function:
    Involved in allantoicase activity
    Specific function:
    The function of this enzyme is unclear as allantoicase activity is not known to exist in mammals.
    Gene Name:
    ALLC
    Uniprot ID:
    Q8N6M5
    Molecular weight:
    43558.25
    Reactions
    Allantoic acid + Water → (S)-Ureidoglycolic acid + Ureadetails
    General function:
    Involved in nucleic acid binding
    Specific function:
    Retroviral proteases have roles in processing of the primary translation products and the maturation of the viral particle. Endogenous Pro proteins may have kept, lost or modified their original function during evolution. This endogenous protein has retained most of the characteristics of retroviral proteases
    Gene Name:
    Not Available
    Uniprot ID:
    P10265
    Molecular weight:
    17107.6
    General function:
    Involved in urea transmembrane transporter activity
    Specific function:
    Not Available
    Gene Name:
    JK
    Uniprot ID:
    Q8WXW8
    Molecular weight:
    3988.6
    General function:
    Involved in urea transmembrane transporter activity
    Specific function:
    Not Available
    Gene Name:
    HUT11
    Uniprot ID:
    Q71UV7
    Molecular weight:
    5627.5

    Transporters

    General function:
    Involved in urea transmembrane transporter activity
    Specific function:
    Specialized low-affinity vasopressin-regulated urea transporter. Mediates rapid transepithelial urea transport across the inner medullary collecting duct and plays a major role in the urinary concentrating mechanism.
    Gene Name:
    SLC14A2
    Uniprot ID:
    Q15849
    Molecular weight:
    101207.965
    References
    1. Wall SM, Han JS, Chou CL, Knepper MA: Kinetics of urea and water permeability activation by vasopressin in rat terminal IMCD. Am J Physiol. 1992 Jun;262(6 Pt 2):F989-98. Pubmed: 1320335
    General function:
    Involved in urea transmembrane transporter activity
    Specific function:
    Specialized low-affinity urea transporter. Mediates urea transport in erythrocytes.
    Gene Name:
    SLC14A1
    Uniprot ID:
    Q13336
    Molecular weight:
    48341.29
    References
    1. Ripoche P, Rousselet G: [Urea transporters]. Nephrologie. 1996;17(7):383-8. Pubmed: 9019665
    2. Olives B, Mattei MG, Huet M, Neau P, Martial S, Cartron JP, Bailly P: Kidd blood group and urea transport function of human erythrocytes are carried by the same protein. J Biol Chem. 1995 Jun 30;270(26):15607-10. Pubmed: 7797558