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Identification
YMDB IDYMDB00003
NameUrea
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUrea is a highly soluble organic compound formed by the deamination of amino acids. It is the principal end product of protein catabolism.
Structure
Thumb
Synonyms
  • Alphadrate
  • Aqua care HP
  • Aquacare HP
  • ARF
  • b-I-K
  • Basodexan
  • beta-I-K
  • Bromisovalum
  • Bubber shet
  • Calmurid
  • Calmurid HC
  • Carbaderm
  • Carbamide
  • Carbamide resin
  • Carbamimic acid
  • Carbamimidic acid
  • Carbonyl diamide
  • Carbonyl diamine
  • Carbonyldiamide
  • Carbonyldiamine
  • Carmol
  • Carmol HC
  • e927b
  • H2NC(O)NH2
  • Harnstoff
  • Helicosol
  • Hyanit
  • Isourea
  • Karbamid
  • Keratinamin
  • Keratinamin kowa
  • Mocovina
  • Onychomal
  • Panafil
  • Pastaron
  • U-cort
  • ur
  • URE
  • Urea
  • Urea perhydrate
  • Ureaphil
  • Uree
  • Ureophil
  • Urepeal
  • Urevert
  • Varioform II
  • 1728
CAS number57-13-6
WeightAverage: 60.0553
Monoisotopic: 60.03236276
InChI KeyXSQUKJJJFZCRTK-UHFFFAOYSA-N
InChIInChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)
IUPAC Nameurea
Traditional IUPAC Nameurea
Chemical FormulaCH4N2O
SMILES[H]N([H])C(=O)N([H])[H]
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
Physical Properties
StateSolid
Charge0
Melting point132 °C
Experimental Properties
PropertyValueReference
Water Solubility545 mg/mL at 25 oC [YALKOWSKY,SH (1989)]PhysProp
LogP-2.11 [HANSCH,C ET AL. (1995)]PhysProp
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 Area69.11 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity13.14 m³·mol⁻¹ChemAxon
Polarizability5.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutamate MetabolismPW002376 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arginine and proline metabolismec00330 Map00330
Purine metabolismec00230 Map00230
Pyrimidine metabolismec00240 Map00240
SMPDB Reactions
L-Arginine + waterOrnithine + Urea
KEGG Reactions
Allantoic acid + waterUrea + Ureidoglycolic acid
L-Arginine + waterOrnithine + Urea
Carbonic acid + Adenosine triphosphate + Ureaphosphate + hydron + ADP + urea-1-carboxylic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Navarathna, D. H., Harris, S. D., Roberts, D. D., Nickerson, K. W. (2010). "Evolutionary aspects of urea utilization by fungi." FEMS Yeast Res 10:209-213.20100286
  • Eisenstein, E., Osborne, J. C. Jr, Chaiken, I. M., Hensley, P. (1984). "Purification and characterization of ornithine transcarbamoylase from Saccharomyces cerevisiae." J Biol Chem 259:5139-5145.6370999
  • Lawther, R. P., Riemer, E., Chojnacki, B., Cooper, T. G. (1974). "Clustering of the genes for allantoin degradation in Saccharomyces cerevisiae." J Bacteriol 119:461-468.4604238
Synthesis Reference:Leuthardt, F.; Glasson, B. Biological synthesis of urea. Verhandl. Ver. schweiz. Physiol. (1942), 21 25-7.
External Links:
ResourceLink
CHEBI ID16199
HMDB IDHMDB00294
Pubchem Compound ID1176
Kegg IDC00086
ChemSpider ID1143
FOODB IDFDB012174
WikipediaUrea
BioCyc IDUREA

Enzymes

General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Hydrolysis of urea to ammonia and CO(2)
Gene Name:
DUR1
Uniprot ID:
P32528
Molecular weight:
201830.0
Reactions
ATP + urea + HCO(3)(-) → ADP + phosphate + urea-1-carboxylate.
Urea-1-carboxylate + H(2)O → 2 CO(2) + 2 NH(3).
General function:
Involved in allantoicase activity
Specific function:
Utilization of purines as secondary nitrogen sources, when primary sources are limiting
Gene Name:
DAL2
Uniprot ID:
P25335
Molecular weight:
38713.5
Reactions
Allantoate + H(2)O → (S)-ureidoglycolate + urea.
General function:
Involved in arginase activity
Specific function:
L-arginine + H(2)O = L-ornithine + urea
Gene Name:
CAR1
Uniprot ID:
P00812
Molecular weight:
35661.60156
Reactions
L-arginine + H(2)O → L-ornithine + urea.

Transporters

General function:
Involved in transporter activity
Specific function:
Required for active transport of urea
Gene Name:
DUR3
Uniprot ID:
P33413
Molecular weight:
80616.10156