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Human Metabolome Database Version 3.5

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Showing metabocard for Urea (HMDB00294)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:15 -0700
HMDB ID HMDB00294
Secondary Accession Numbers None
Metabolite Identification
Common Name Urea
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula CH4N2O
Average Molecular Weight 60.0553
Monoisotopic Molecular Weight 60.03236276
IUPAC Name urea
Traditional IUPAC Name urea
CAS Registry Number 57-13-6
SMILES NC(N)=O
InChI Identifier InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
InChI Key XSQUKJJJFZCRTK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Ureas
Sub Class N/A
Other Descriptors
  • a small molecule(Cyc)
  • isourea(ChEBI)
Substituents
  • N/A
Direct Parent Ureas
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
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)
Predicted Properties
Property Value Source
Water Solubility 412 g/L ALOGPS
LogP -1.78 ALOGPS
LogP -1.4 ChemAxon
LogS 0.84 ALOGPS
pKa (strongest acidic) 15.73 ChemAxon
pKa (strongest basic) -2.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 69.11 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 13.14 ChemAxon
Polarizability 5.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Prostate
  • Skin
Pathways
Name SMPDB Link KEGG Link
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Urea Cycle SMP00059 map00330 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
6074.6 +/- 2154.2 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
4530.0 (2590.0 - 6470.0) uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
4010.0 +/- 920.0 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
3600.0 (2680.0 - 4780.0) uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
5210.0 (4310.0 - 6780.0) uM Children (1-13 year old) Not Specified Normal Children (1-6 years)
Blood Detected and Quantified
Article_icon
6500.0 (4000.0-9000.0) uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
2960 +/- 1000 uM Adult (>18 years old) Female Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
3820.0 (0.0-7640.0) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
4160.0 (2300.0-6060.0) uM Adult (>18 years old) Both Normal Not Available
Saliva Detected and Quantified
Article_icon
1-6985 uM Adult (>18 years old) Male normal At rest without stimulation
Saliva Detected and Quantified
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1-9528 uM Adult (>18 years old) Male normal Salivary induction with a citric acid solution...
Urine Detected and Quantified
Article_icon
15491.64-38812.40 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
22566.0 +/- 4407.0 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
6286.43 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
12285 (174-49097) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and Quantified
29.6 (6.579-52.6) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
3500.0 +/- 1500.0 uM Adult (>18 years old) Both Cirrhosis Not Available
Blood Detected and Quantified
Article_icon
3309.9 +/- 1844 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
1800.0 (1500.0-2100.0) uM Adult (>18 years old) Both Tuberculosis Meningitis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2150.0 (1850.0-2450.0) uM Adult (>18 years old) Both Meningitis Bacterial
Associated Disorders and Diseases
Disease References
Tuberculous meningitis
  • 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 Link_out
    Meningitis
    • 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 Link_out
      Cirrhosis
      • 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 Link_out
        Associated OMIM IDs None
        DrugBank ID DB03904 Link_out
        Phenol Explorer Compound ID Not Available
        Phenol Explorer Metabolite ID Not Available
        FoodDB ID FDB012174
        KNApSAcK ID C00007314 Link_out
        Chemspider ID 1143 Link_out
        KEGG Compound ID C00086 Link_out
        BioCyc ID UREA Link_out
        BiGG ID 33799 Link_out
        Wikipedia Link Urea Link_out
        NuGOwiki Link HMDB00294 Link_out
        Metagene Link HMDB00294 Link_out
        METLIN ID 6 Link_out
        PubChem Compound 1176 Link_out
        PDB ID URE Link_out
        ChEBI ID 16199 Link_out
        References
        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)
        General References
        1. 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 Link_out
        2. Vaidya VS, Bonventre JV: Mechanistic biomarkers for cytotoxic acute kidney injury. Expert Opin Drug Metab Toxicol. 2006 Oct;2(5):697-713. Pubmed: 17014390 Link_out
        3. 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 Link_out
        4. 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 Link_out
        5. 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 Link_out
        6. 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 Link_out
        7. 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 Link_out
        8. 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 Link_out
        9. 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 Link_out
        10. Final report of the safety assessment of Urea. Int J Toxicol. 2005;24 Suppl 3:1-56. Pubmed: 16422263 Link_out
        11. 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 Link_out
        12. 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 Link_out
        13. Hobbs JR: Monitoring myelomatosis. Arch Intern Med. 1975 Jan;135(1):125-30. Pubmed: 1111461 Link_out
        14. 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 Link_out
        15. 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 Link_out
        16. 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 Link_out
        17. 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 Link_out
        18. 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 Link_out
        19. 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 Link_out
        20. 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 Link_out
        Enzymes
        Name: Arginase-1
        Reactions:
        • L-arginine + H2O = L-ornithine + urea [RN:R00551]
        Gene Name: ARG1
        Uniprot ID: P05089 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Arginase-2, mitochondrial
        Reactions:
        • L-arginine + H2O = L-ornithine + urea [RN:R00551]
        Gene Name: ARG2
        Uniprot ID: P78540 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Carbonic anhydrase 2
        Reactions:
        • H2CO3 = CO2 + H2O [RN:R00132]
        Gene Name: CA2
        Uniprot ID: P00918 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Catenin beta-1
        Reactions:
          Gene Name: CTNNB1
          Uniprot ID: P35222 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Agmatinase, mitochondrial
          Reactions:
          • agmatine + H2O = putrescine + urea [RN:R01157]
          Gene Name: AGMAT
          Uniprot ID: Q9BSE5 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: G-protein coupled receptor family C group 6 member A
          Reactions:
            Gene Name: GPRC6A
            Uniprot ID: Q5T6X5 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Probable allantoicase
            Reactions:
            • allantoate + H2O = (S)-ureidoglycolate + urea [RN:R02422]
            Gene Name: ALLC
            Uniprot ID: Q8N6M5 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: HERV-K_5q33.3 provirus ancestral Pro protein
            Reactions:
            • Processing at the authentic HIV-1 PR recognition site and release of the mature p17 matrix and the p24 capsid protein, as a result of the cleavage of the -SQNY!PIVQ- cleavage site.
            Gene Name: Not Available
            Uniprot ID: P10265 Link_out
            Protein Sequence: FASTA
            Name: Urea transporter JK glycoprotein
            Reactions:
              Gene Name: JK
              Uniprot ID: Q8WXW8 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Blood group Kidd urea transporter
              Reactions:
                Gene Name: HUT11
                Uniprot ID: Q71UV7 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Transporters
                Name: Urea transporter 2
                Reactions:
                • --- []
                Gene Name: SLC14A2
                Uniprot ID: Q15849 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Urea transporter 1
                Reactions:
                  Gene Name: SLC14A1
                  Uniprot ID: Q13336 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA