Record Information
Version2.0
Creation Date2012-05-31 13:55:05 -0600
Update Date2015-06-03 15:54:13 -0600
Secondary Accession Numbers
  • ECMDB02031
Identification
Name:Ureidoisobutyric acid
DescriptionBeta-ureidoisobutyrate is an intermediate of pyrimidine metabolism. It is converted from and to dihydrothymine by d-phenylhydantoinase. (KEGG)
Structure
Thumb
Synonyms:
  • 3-Carbamoylamino-2-methylpropanoate
  • 3-Carbamoylamino-2-methylpropanoic acid
  • 3-Ureidoisobutyrate
  • 3-Ureidoisobutyric acid
  • N-carbamyl-β-aminoisobutyrate
  • N-carbamyl-β-aminoisobutyric acid
  • b-Uba
  • b-Ureidoisobutyrate
  • b-Ureidoisobutyric acid
  • Beta-Uba
  • Beta-Ureidoisobutyrate
  • Beta-Ureidoisobutyric acid
  • DL-b-Ureidoisobutyrate
  • DL-b-Ureidoisobutyric acid
  • DL-beta-Ureidoisobutyrate
  • DL-beta-Ureidoisobutyric acid
  • DL-β-Ureidoisobutyrate
  • DL-β-Ureidoisobutyric acid
  • n-Carbamyl-β-aminoisobutyrate
  • n-Carbamyl-β-aminoisobutyric acid
  • N-Carbamyl-amino isobutyrate
  • N-Carbamyl-amino isobutyric acid
  • N-Carbamyl-b-aminoisobutyrate
  • N-Carbamyl-b-aminoisobutyric acid
  • N-Carbamyl-beta-aminoisobutyrate
  • N-Carbamyl-beta-aminoisobutyric acid
  • N-Carbamyl-β-aminoisobutyrate
  • N-Carbamyl-β-aminoisobutyric acid
  • Ureidoisobutyrate
  • β-Uba
  • β-Ureidoisobutyrate
  • β-Ureidoisobutyric acid
Chemical Formula:C5H10N2O3
Weight:Average: 146.1445
Monoisotopic: 146.069142196
InChI Key:PHENTZNALBMCQD-UHFFFAOYSA-N
InChI:InChI=1S/C5H10N2O3/c1-3(4(8)9)2-7-5(6)10/h3H,2H2,1H3,(H,8,9)(H3,6,7,10)
CAS number:2905-86-4
IUPAC Name:3-(carbamoylamino)-2-methylpropanoic acid
Traditional IUPAC Name:β-ureidoisobutyric acid
SMILES:CC(CNC(N)=O)C(O)=O
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
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility46.1 g/LALOGPS
logP-0.86ALOGPS
logP-0.88ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)4.32ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.4 m³·mol⁻¹ChemAxon
Polarizability13.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-5fb552346f153d8b9141View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9510000000-6396a4042b792437e39aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ug1-4900000000-57fe49b6570a3a56075eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9400000000-d75bc53f6bd893972265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-505e1e587ff8e3f47c4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-6900000000-d0e112adeac57b5cc676View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-9600000000-38cc35413fc058ff2f4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-46efbc5db1bc9c62db04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-8900000000-51286b64a41bad89fd80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gi-9100000000-835c9b02eecbd89baac8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-40f2b4e3a071943603eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3900000000-9dfc177176195ee47192View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-0f56471f86b7f2230673View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-60a7db0ec3c9213e9347View in MoNA
References
References:
  • Hofmann U, Schwab M, Seefried S, Marx C, Zanger UM, Eichelbaum M, Murdter TE: Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 5;791(1-2):371-80. Pubmed: 12798197
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Ohse M, Matsuo M, Ishida A, Kuhara T: Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. J Mass Spectrom. 2002 Sep;37(9):954-62. Pubmed: 12271438
Synthesis Reference:Evans, W. R.; Tsai, Chi Shiun; Axelrod, Bernard. Origin of b-aminoisobutyric acid in iris. Nature (London, United Kingdom) (1961), 190 809.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1670
HMDB IDHMDB02031
Pubchem Compound ID160663
Kegg IDC05100
ChemSpider ID141172
Wikipedia IDNot Available
BioCyc ID3-UREIDO-ISOBUTYRATE
EcoCyc ID3-UREIDO-ISOBUTYRATE

Enzymes

General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
Specific function:
Catalyzes the stereospecific hydrolysis of the cyclic amide bond of D-hydantoin derivatives with an aromatic side chains at the 5'-position. Has no activity on dihydropyrimidines. The physiological function is unknown
Gene Name:
hyuA
Uniprot ID:
Q46806
Molecular weight:
51025