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Bovine Metabolome Database



Showing metabocard for Ureidopropionic acid (BMDB00026)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:38
Accession Number BMDB00026
Common 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.
Synonyms
  1. 3-Ureido-propionate
  2. 3-Ureidopropionate
  3. 3-Ureidopropionic acid
  4. Carbamoyl-b-Ala-OH
  5. N-(aminocarbonyl)-'b-Alanine
  6. N-(aminocarbonyl)-beta-Alanine
  7. N-Carbamoyl-beta-alanine
  8. Ureidopropionate
  9. Ureidopropionic acid
  10. beta-Ureidopropionate
  11. beta-Ureidopropionic acid
  12. Carbamoyl-beta-Ala-OH
  13. 3-ureidopropanoate
  14. 3-ureidopropanoic acid
  15. N-carbamoyl-b-alanine
  16. 3-(carbamoylamino)propanoic acid
  17. N-(aminocarbonyl)-b-alanine
  18. 3-(carbamoylamino)propanoate
Chemical IUPAC Name 3-carbamoylaminopropanoic acid
Chemical Formula C4H8N2O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • carboxylic acid; urea
Biofunction
  • Component of beta-Alanine metabolism; Component of Pantothenate and CoA biosynthesis; Component of Pyrimidine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 132.118
Monoisotopic Molecular Weight 132.053497
Isomeric SMILES NC(=O)NCCC(O)=O
Canonical SMILES NC(=O)NCCC(O)=O
KEGG Compound ID C02642 Link Image
BioCyc ID 3-UREIDO-PROPIONATE Link Image
BiGG ID 40270 Link Image
Wikipedia Link Not Available
METLIN ID 5097 Link Image
PubChem Compound 111 Link Image
PubChem Substance 10322862 Link Image
ChEBI ID 18261 Link Image
CAS Registry Number 462-88-4
InChI Identifier InChI=1/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)
Synthesis Reference w-Ureido carboxylic acids. (1962), 3 pp. GB 913713 19621228 CAN 58:72975 AN 1963:72975
Melting Point (Experimental) 170 oC
Experimental Water Solubility 20.9 mg/mL [BEILSTEIN] Source: PhysProp
Predicted Water Solubility 52.7 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.98 [Predicted by ALOGPS]; -1.6 [Predicted by PubChem via XLOGP]; -1.34 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Beta Alanine Metabolism
  • Pantothenate and CoA Biosynthesis
  • Pyrimidine Metabolism
HMDB Pathways
Name Beta Alanine Metabolism
Image Show Link Image
Name Pantothenate and CoA Biosynthesis
Image Show Link Image
Name Pyrimidine Metabolism
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KEGG Pathways
Name Beta Alanine Metabolism
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Name Pantothenate and CoA Biosynthesis
Image Show Link Image
Name Pyrimidine Metabolism
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SimCell Pathways
Name Beta Alanine Metabolism
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Graph
SBML
Name Pyrimidine Metabolism
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Graph
SBML
General References Not Available