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Record Information
Version1.0
Creation Date2016-09-30 22:27:58 UTC
Update Date2020-06-04 21:45:44 UTC
BMDB IDBMDB0000294
Secondary Accession Numbers
  • BMDB00294
Metabolite Identification
Common NameUrea
DescriptionUrea, 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.
Structure
Thumb
Synonyms
ValueSource
1728ChEBI
CarbamideChEBI
CarbonyldiamideChEBI
e927bChEBI
H2NC(O)NH2ChEBI
HarnstoffChEBI
KarbamidChEBI
urChEBI
UreeChEBI
PastaronKegg
AlphadrateHMDB
ARFHMDB
b-I-KHMDB
beta-I-KHMDB
BromisovalumHMDB
Bubber shetHMDB
CalmuridHMDB
Calmurid HCHMDB
CarbadermHMDB
Carbamide resinHMDB
Carbonyl diamideHMDB
Carbonyl diamineHMDB
CarbonyldiamineHMDB
CarmolHMDB
HelicosolHMDB
HyanitHMDB
IsoureaHMDB
KeratinaminHMDB
Keratinamin kowaHMDB
MocovinaHMDB
OnychomalHMDB
PanafilHMDB
UREHMDB
UreaphilHMDB
UreophilHMDB
BasodexanHMDB
Chemical FormulaCH4N2O
Average Molecular Weight60.0553
Monoisotopic Molecular Weight60.03236276
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number57-13-6
SMILESNot Available
InChI Identifier
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
InChI KeyXSQUKJJJFZCRTK-UHFFFAOYSA-N
Chemical Taxonomy
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.
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Epidermis
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1321 +/- 282 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified6510 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified2430-2890 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified732.658-3603.346 uMNot SpecifiedNot Specified
Normal
    • Arthur K. Anderso...
details
BloodDetected and Quantified1145.611 +/- 449.586 uMNot SpecifiedNot Specified
Normal
    • C. R. E. Cogginsa...
details
BloodDetected and Quantified3840-4110 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified4121-4443 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified1950-4080 uMNot SpecifiedNot Specified
Normal
    • Liker B., L. Bač...
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2331.196 - 2381.151 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5944.551 - 6144.368 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified282.72 +/- 45.21 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1117 +/- 175 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1174 +/- 115 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1115 +/- 30 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1104 +/- 136 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4110 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified4570 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified5150 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6130 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6450 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6490 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6570 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6850 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6890 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified7160 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified7310 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified7480 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2250 +/- 140 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2250 +/- 300 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2460 +/- 170 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2700 +/- 120 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2930 +/- 110 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified4329.365 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified221.68 +/- 102.60 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified389.71 +/- 57.62 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified1870 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified2920 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified2570 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified890 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified1872 +/- 1191 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified2928 +/- 1634 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified1977 +/- 792 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified898 +/- 84 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified898.83 +/- 984.41 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Heat stress
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
BloodDetected and Quantified5570 uMNot SpecifiedNot Specified
Treated with bovine somatotropin
details
Ruminal FluidDetected and Quantified2577.19 +/- 767.12 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000294
DrugBank IDDB03904
Phenol Explorer Compound IDNot Available
FooDB IDFDB012174
KNApSAcK IDC00007314
Chemspider ID1143
KEGG Compound IDC00086
BioCyc IDUREA
BiGG ID33799
Wikipedia LinkUrea
METLIN ID6
PubChem Compound1176
PDB IDNot Available
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)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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.
  9. 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.

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
ARG1
Uniprot ID:
Q2KJ64
Molecular weight:
35009.0
Reactions
L-Arginine + Water → Ornithine + Ureadetails
General function:
Amino acid transport and metabolism
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 nitric oxid synthase (NOS). Arginine metabolism is a critical regulator of innate and adaptive immune responses. Seems to be involved in negative regulation of the survival capacity of activated T cells. May suppress inflammation-related signaling in asthmatic airway epithelium. May play a role in promoting prenatal immune suppression. Regulates RPS6KB1 signaling, which promotes endothelial cell senescence and inflammation and implicates NOS3/eNOS dysfunction. Can inhibit endothelial autophagy independently of its enzymatic activity implicating mTORC2 signaling. Involved in vascular smooth muscle cell senescence and apoptosis independently of its enzymatic activity.
Gene Name:
ARG2
Uniprot ID:
Q58DL1
Molecular weight:
38616.0
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:
Q2KIG4
Molecular weight:
46084.0
General function:
Involved in urea transmembrane transporter activity
Specific function:
Urea channel that facilitates transmembrane urea transport down a concentration gradient. A constriction of the transmembrane channel functions as selectivity filter through which urea is expected to pass in dehydrated form. The rate of urea conduction is increased by hypotonic stress. Plays an important role in the kidney medulla collecting ducts, where it allows rapid equilibration between the lumen of the collecting ducts and the interstitium, and thereby prevents water loss driven by the high concentration of urea in the urine. Facilitates urea transport across erythrocyte membranes. May also play a role in transmembrane water transport, possibly by indirect means.
Gene Name:
SLC14A1
Uniprot ID:
Q5QF96
Molecular weight:
41473.0