Record Information
Version2.0
Creation Date2012-05-31 09:55:28 -0600
Update Date2015-09-13 12:56:05 -0600
Secondary Accession Numbers
  • ECMDB00026
Identification
Name:Ureidopropionic acid
Description:Ureidopropionic acid is an intermediate in the metabolism of uracil. More specifically it is a breakdown product of dihydrouracil and is produced by the enzyme dihydropyrimidase. It is further decomposed to beta-alanine via the enzyme beta-ureidopropionase. Ureidopropionic acid is essentially a urea derivative of beta-alanine. High levels of Ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency [PMID: 11675655]. Enzyme deficiencies in pyrimidine metabolism are associated with a risk for severe toxicity against the antineoplastic agent 5-fluorouracil.
Structure
Thumb
Synonyms:
  • β-ureidopropionate
  • β-ureidopropionic acid
  • 3-(Carbamoylamino)propanoate
  • 3-(Carbamoylamino)propanoic acid
  • 3-Ureido-propionate
  • 3-Ureido-propionic acid
  • 3-Ureidopropanoate
  • 3-Ureidopropanoic acid
  • 3-Ureidopropionate
  • 3-Ureidopropionic acid
  • N-carbamoyl-β-alanine
  • b-Ureidopropionate
  • b-Ureidopropionic acid
  • Beta-Ureidopropionate
  • Beta-Ureidopropionic acid
  • Carbamoyl-b-Ala-OH
  • Carbamoyl-beta-Ala-OH
  • Carbamoyl-β-ala-OH
  • N-(Aminocarbonyl)-'b-Alanine
  • N-(Aminocarbonyl)-b-alanine
  • N-(Aminocarbonyl)-beta-Alanine
  • N-(Aminocarbonyl)-β-alanine
  • n-Carbamoyl-β-alanine
  • N-Carbamoyl-b-alanine
  • N-Carbamoyl-beta-alanine
  • N-Carbamoyl-β-alanine
  • N-Carbamyl-b-alanine
  • N-Carbamyl-beta-alanine
  • N-Carbamyl-β-alanine
  • Ureidopropionate
  • Ureidopropionic acid
  • β-Ureidopropionate
  • β-Ureidopropionic acid
Chemical Formula:C4H8N2O3
Weight:Average: 132.1179
Monoisotopic: 132.053492132
InChI Key:JSJWCHRYRHKBBW-UHFFFAOYSA-N
InChI:InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)
CAS number:462-88-4
IUPAC Name:3-(carbamoylamino)propanoic acid
Traditional IUPAC Name:ureidopropionic acid
SMILES:NC(=O)NCCC(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as ureas. These are compounds containing two amine groups joined by a carbonyl (C=O) functional group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic carbonic acids and derivatives
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:170 °C
Experimental Properties:
PropertyValueSource
Water Solubility:20.9 mg/mL [BEILSTEIN]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility52.7 mg/mLALOGPS
logP-0.98ALOGPS
logP-1.4ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.82 m3·mol-1ChemAxon
Polarizability12.07 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 Pw000828Pw000828 greyscalePw000828 simple
Pyrimidine metabolismPW000942 Pw000942Pw000942 greyscalePw000942 simple
beta-Alanine metabolismPW000896 Pw000896Pw000896 greyscalePw000896 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-002f-3910000000-bbd51b3bb30ff8d230d3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00n0-5900000000-00dc280a63401c96ec2aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-2930000000-fcdce5cf4a20023c403aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0hr0-2900000000-8a898fc59206b3f30a13View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-006x-9000000000-f7cdf5fc49adf0b5e726View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-002f-3910000000-bbd51b3bb30ff8d230d3View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00n0-5900000000-00dc280a63401c96ec2aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-2930000000-fcdce5cf4a20023c403aView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0hr0-2900000000-8a898fc59206b3f30a13View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udj-1910000000-83ab1eb4328f8caae993View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0v01-0900000000-aeacd84d8e0e91418232View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00dr-9300000000-7b12845cd5bc4d02874cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00r6-9500000000-7ea8c95e3dc6296a07e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9100000000-7b61b087fbf6c821bdd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0596-9200000000-79dfb7a1a6838745e178View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014l-8900000000-9bfe2297b9071d10d7e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-7900000000-684d9877d084bfc7c955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9100000000-0b6f9ea311703e9ecf13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9000000000-1cb23a8265b882313309View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001c-9300000000-2cec50bd5b226a288c82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9100000000-63ecd2f9ef02c677503dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-396bc860a5f8f06ff7c5View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Desmoulin F, Gilard V, Malet-Martino M, Martino R: Metabolism of capecitabine, an oral fluorouracil prodrug: (19)F NMR studies in animal models and human urine. Drug Metab Dispos. 2002 Nov;30(11):1221-9. Pubmed: 12386128
  • 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
  • Ito S, Kawamura T, Inada M, Inoue Y, Hirao Y, Koga T, Kunizaki J, Shimizu T, Sato H: Physiologically based pharmacokinetic modelling of the three-step metabolism of pyrimidine using C-uracil as an in vivo probe. Br J Clin Pharmacol. 2005 Dec;60(6):584-93. Pubmed: 16305582
  • 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
  • Malet-Martino MC, Armand JP, Lopez A, Bernadou J, Beteille JP, Bon M, Martino R: Evidence for the importance of 5'-deoxy-5-fluorouridine catabolism in humans from 19F nuclear magnetic resonance spectrometry. Cancer Res. 1986 Apr;46(4 Pt 2):2105-12. Pubmed: 2936452
  • Moolenaar, S. H., Gohlich-Ratmann, G., Engelke, U. F., Spraul, M., Humpfer, E., Dvortsak, P., Voit, T., Hoffmann, G. F., Brautigam, C., van Kuilenburg, A. B., van Gennip, A., Vreken, P., Wevers, R. A. (2001). "beta-Ureidopropionase deficiency: a novel inborn error of metabolism discovered using NMR spectroscopy on urine." Magn Reson Med 46:1014-1017. Pubmed: 11675655
  • Patel BN, West TP. 1987. "Degradation of the pyrimidine bases uracil and thymine by Escherichia coli B." Microbios 49(199):107-13 Pubmed: 3553866
  • Simaga S, Kos E. 1978. "Uracil catabolism by Escherichia coli K12S." Z Naturforsch C 33(11-12):1006-8 Pubmed: 154218
  • Sparidans RW, Bosch TM, Jorger M, Schellens JH, Beijnen JH: Liquid chromatography-tandem mass spectrometric assay for the analysis of uracil, 5,6-dihydrouracil and beta-ureidopropionic acid in urine for the measurement of the activities of the pyrimidine catabolic enzymes. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jul 24;839(1-2):45-53. Epub 2006 Feb 28. Pubmed: 16513432
Synthesis Reference:w-Ureido carboxylic acids. (1962), 3 pp. GB 913713 19621228 CAN 58:72975 AN 1963:72975
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18261
HMDB IDHMDB00026
Pubchem Compound ID111
Kegg IDC02642
ChemSpider ID109
Wikipedia ID3-Ureidopropionic_acid
BioCyc ID3-UREIDO-PROPIONATE
EcoCyc ID3-UREIDO-PROPIONATE
Ligand ExpoURP

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
General function:
Involved in oxidoreductase activity
Specific function:
Specific function unknown
Gene Name:
yeiT
Uniprot ID:
P76440
Molecular weight:
44329
Reactions
5,6-dihydrouracil + NAD(+) = uracil + NADH.
5,6-dihydrothymine + NAD(+) = thymine + NADH.