3-ureidopropanoate (PAMDB110176)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110176
Identification
Name: 3-ureidopropanoate
Description:A monocarboxylic acid anion that is the conjugate base of N-carbamoyl-β-alanine arising from deprotonation of the carboxy group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3-ureidopropionate
  • β-ureidopropionic acid
  • N-carbamoyl-β-alanine
Chemical Formula: C4H7N2O3
Average Molecular Weight: 131.11
Monoisotopic Molecular Weight: 132.0534921335
InChI Key: JSJWCHRYRHKBBW-UHFFFAOYSA-M
InChI: InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)/p-1
CAS number: 462-88-4
IUPAC Name:3-(carbamoylamino)propanoate
Traditional IUPAC Name: ureidopropionic acid
SMILES:C(NC(=O)N)CC([O-])=O
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassOrganic carbonic acids and derivatives
Direct Parent Ureas
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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 170 °C
Experimental Properties:
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility20.9 mg/mLNot Available
LogPNot AvailableNot Available
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: Not Available
Reactions:
Pathways:
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
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Moolenaar SH, Gohlich-Ratmann G, Engelke UF, Spraul M, Humpfer E, Dvortsak P, Voit T, Hoffmann GF, Brautigam C, van Kuilenburg AB, van Gennip A, Vreken P, Wevers RA: beta-Ureidopropionase deficiency: a novel inborn error of metabolism discovered using NMR spectroscopy on urine. Magn Reson Med. 2001 Nov;46(5):1014-7. [11675655 ]
  • 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. [16513432 ]
  • 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. [16305582 ]
  • 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. [12798197 ]
  • 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. [2936452 ]
  • 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. [12386128 ]
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
ChEBI11892
ChemSpider5342107
HMDBHMDB00026
KEGGC02642
MetaboLightsMTBLC11892
PubChem6971254