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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 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
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-alanineHMDB
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-1.5ALOGPS
logP-1.4ChemAxon
logS-1.6ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-002f-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-MS (Non-derivatized)splash10-002f-3910000000-bbd51b3bb30ff8d230d3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00n0-5900000000-00dc280a63401c96ec2aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-2930000000-fcdce5cf4a20023c403aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0hr0-2900000000-8a898fc59206b3f30a13View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udj-1910000000-83ab1eb4328f8caae993View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0v01-0900000000-aeacd84d8e0e91418232View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-f7cdf5fc49adf0b5e726View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-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 AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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 IDHMDB0000026
FooDB IDFDB030466
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID40270
BioCyc ID3-UREIDO-PROPIONATE
METLIN ID5097
PDB IDURP
Wikipedia Link3-Ureidopropionic_acid
Chemspider ID109
ChEBI ID18261
PubChem Compound ID111
Kegg Compound IDC02642
YMDB IDNot Available
ECMDB IDE
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 ]