Showing metabocard for Urea (BMDB0000294)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
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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
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaCH4N2O
Average Molecular Weight60.0553
Monoisotopic Molecular Weight60.03236276
IUPAC Nameurea
Traditional 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
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 Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.14 m³·mol⁻¹ChemAxon
Polarizability5.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-234545ed5860ba077237View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0079-3900000000-0ef80e5f5cd9dd6bd213View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02tc-9000000000-d69da17ffbb84fb6bdcaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-234545ed5860ba077237View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0079-3900000000-0ef80e5f5cd9dd6bd213View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1900000000-d805e3019d86aaf9fec0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9000000000-400d59bf59b857bd7c06View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01ot-9000000000-91554974873c3217dc93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03di-9000000000-9d3431eab9093f365e2bView 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052f-9000000000-39cd266ec67397ab213fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-9000000000-95a1106bd10162ddd326View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-b759ce75f0e73d2777dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fd9f25340762315b4515View in MoNA
MSMass Spectrum (Electron Ionization)splash10-02tc-9000000000-871569893ccfa5dd5395View in MoNA
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, acetone+DMSO+tetramethylurea, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Epidermis
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
  • Urine
Pathways
Normal Concentrations
Abnormal Concentrations
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

Enzyme Details
1. Arginase-1
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
Enzyme Details
2. Arginase-2, mitochondrial
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
Enzyme Details
3. Probable allantoicase
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
Enzyme Details
4. Urea transporter 1
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