You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:22:15 UTC
Update Date2016-07-20 20:48:21 UTC
LmdbLMDB00008
Secondary Accession NumbersNone
Metabolite Identification
Common NameUreidopropionic acid
DescriptionUreidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-b-alanine, 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. Ureidopropionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Ureidopropionic acid exists in all living organisms, ranging from bacteria to humans. Within humans, ureidopropionic acid participates in a number of enzymatic reactions. In particular, ureidopropionic acid can be converted into β-alanine through its interaction with the enzyme Beta-ureidopropionase. In addition, ureidopropionic acid can be biosynthesized from dihydrouracil through its interaction with the enzyme dihydropyrimidinase. In humans, ureidopropionic acid is involved in beta-alanine metabolism. A beta-alanine derivative that is propionic acid bearing a ureido group at position 3. Outside of the human body, Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheats, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods. Ureidopropionic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
3-[(Aminocarbonyl)amino]propanoic acidChEBI
3-UreidopropanoateChEBI
3-Ureidopropanoic acidChEBI
3-UreidopropionateChEBI
3-Ureidopropionic acidChEBI
beta-Ureidopropionic acidChEBI
N-(AMINOCARBONYL)-BETA-alanineChEBI
Ureidopropanoic acidChEBI
N-Carbamoyl-beta-alanineKegg
3-[(Aminocarbonyl)amino]propanoateGenerator
b-UreidopropionateGenerator
b-Ureidopropionic acidGenerator
beta-UreidopropionateGenerator
Β-ureidopropionateGenerator
Β-ureidopropionic acidGenerator
N-(AMINOCARBONYL)-b-alanineGenerator
N-(AMINOCARBONYL)-β-alanineGenerator
UreidopropanoateGenerator
N-Carbamoyl-b-alanineGenerator
N-Carbamoyl-β-alanineGenerator
UreidopropionateGenerator
3-(carbamoylamino)PropanoateHMDB
3-(carbamoylamino)Propanoic acidHMDB
3-ureido-PropionateHMDB
Carbamoyl-b-ala-OHHMDB
Carbamoyl-beta-ala-OHHMDB
N-(Aminocarbonyl)-'b-alanineHMDB
N-Carbamyl-b-alanineHMDB
N-Carbamyl-beta-alanineHMDB
Ion(-1) OF N-carbamoyl-beta-alanineMeSH, HMDB
Carbamoyl-beta-alanineHMDB
Carbamoyl-β-alanineHMDB
Carbamyl beta-alanineHMDB
Carbamyl β-alanineHMDB
beta-Ureidopropanoic acidHMDB
β-Ureidopropanoic acidHMDB
Chemical FormulaC4H8N2O3
Average Molecular Weight132.1179
Monoisotopic Molecular Weight132.053492132
IUPAC Name3-(carbamoylamino)propanoic acid
Traditional Nameureidopropionic acid
CAS Registry Number462-88-4
SMILES
NC(=O)NCCC(O)=O
InChI Identifier
InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)
InChI KeyJSJWCHRYRHKBBW-UHFFFAOYSA-N
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.82 m³·mol⁻¹ChemAxon
Polarizability12.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-3910000000-bbd51b3bb30ff8d230d3Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00n0-5900000000-00dc280a63401c96ec2aSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-2930000000-fcdce5cf4a20023c403aSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0hr0-2900000000-8a898fc59206b3f30a13Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-3910000000-bbd51b3bb30ff8d230d3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00n0-5900000000-00dc280a63401c96ec2aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2930000000-fcdce5cf4a20023c403aSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0hr0-2900000000-8a898fc59206b3f30a13Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-1910000000-83ab1eb4328f8caae993Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0v01-0900000000-aeacd84d8e0e91418232Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-f7cdf5fc49adf0b5e726Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9300000000-7b12845cd5bc4d02874cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00r6-9500000000-7ea8c95e3dc6296a07e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9100000000-7b61b087fbf6c821bdd0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0596-9200000000-79dfb7a1a6838745e178Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014l-8900000000-9bfe2297b9071d10d7e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-7900000000-684d9877d084bfc7c955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9100000000-0b6f9ea311703e9ecf13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9000000000-1cb23a8265b882313309Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001c-9300000000-2cec50bd5b226a288c82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9100000000-63ecd2f9ef02c677503dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-396bc860a5f8f06ff7c5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
UrineDetected and Quantified347 umol/mmol creatinineNot AvailablePorcine details
UrineDetected and Quantified615 umol/mmol creatinineNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0062812
FooDB IDFDB030466
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID3-UREIDO-PROPIONATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link3-Ureidopropionic_acid
Chemspider ID109
ChEBI ID18261
PubChem Compound ID111
Kegg Compound IDC02642
YMDB IDNot Available
ECMDB IDECMDB00026
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]