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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-27 20:29:27 UTC
HMDB IDHMDB0000026
Secondary Accession Numbers
  • HMDB00026
  • HMDB0062812
  • HMDB62812
Metabolite Identification
Common NameUreidopropionic acid
DescriptionUreidopropionic acid, also known as 3-ureidopropanoate or N-carbamoyl-beta-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 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 into 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. Ureidopropionic acid has been detected, but not quantified in, several different foods, such as gram beans, broccoli, climbing beans, oriental wheat, and mandarin orange (clementine, tangerine). This could make ureidopropionic acid a potential biomarker for the consumption of these foods.
Structure
Data?1582752108
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility20.9 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility52.7 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.11431661259
DarkChem[M+H]+128.11431661259
DarkChem[M-H]-122.32631661259
DarkChem[M-H]-122.32631661259
AllCCS[M+H]+130.8232859911
AllCCS[M-H]-126.42132859911
DeepCCS[M+H]+128.63630932474
DeepCCS[M-H]-125.71730932474
DeepCCS[M-2H]-162.13630932474
DeepCCS[M+Na]+137.230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ureidopropionic acidNC(=O)NCCC(O)=O2311.6Standard polar33892256
Ureidopropionic acidNC(=O)NCCC(O)=O1450.7Standard non polar33892256
Ureidopropionic acidNC(=O)NCCC(O)=O1734.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ureidopropionic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCNC(N)=O1590.3Semi standard non polar33892256
Ureidopropionic acid,1TMS,isomer #2C[Si](C)(C)NC(=O)NCCC(=O)O1614.3Semi standard non polar33892256
Ureidopropionic acid,1TMS,isomer #3C[Si](C)(C)N(CCC(=O)O)C(N)=O1609.2Semi standard non polar33892256
Ureidopropionic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C1675.0Semi standard non polar33892256
Ureidopropionic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C1475.1Standard non polar33892256
Ureidopropionic acid,2TMS,isomer #1C[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C2282.5Standard polar33892256
Ureidopropionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C1585.2Semi standard non polar33892256
Ureidopropionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C1559.0Standard non polar33892256
Ureidopropionic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C2393.3Standard polar33892256
Ureidopropionic acid,2TMS,isomer #3C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C1727.3Semi standard non polar33892256
Ureidopropionic acid,2TMS,isomer #3C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C1609.8Standard non polar33892256
Ureidopropionic acid,2TMS,isomer #3C[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C2317.0Standard polar33892256
Ureidopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C1701.1Semi standard non polar33892256
Ureidopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C1661.7Standard non polar33892256
Ureidopropionic acid,2TMS,isomer #4C[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C2219.5Standard polar33892256
Ureidopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C1719.3Semi standard non polar33892256
Ureidopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C1597.6Standard non polar33892256
Ureidopropionic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C)[Si](C)(C)C1982.7Standard polar33892256
Ureidopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1671.7Semi standard non polar33892256
Ureidopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1619.3Standard non polar33892256
Ureidopropionic acid,3TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C)[Si](C)(C)C1935.4Standard polar33892256
Ureidopropionic acid,3TMS,isomer #3C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C1745.9Semi standard non polar33892256
Ureidopropionic acid,3TMS,isomer #3C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C1787.0Standard non polar33892256
Ureidopropionic acid,3TMS,isomer #3C[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C1926.1Standard polar33892256
Ureidopropionic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1756.3Semi standard non polar33892256
Ureidopropionic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1769.4Standard non polar33892256
Ureidopropionic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1725.3Standard polar33892256
Ureidopropionic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCNC(N)=O1832.7Semi standard non polar33892256
Ureidopropionic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O1867.0Semi standard non polar33892256
Ureidopropionic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(N)=O1813.5Semi standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C2114.6Semi standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C1865.0Standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC(=O)O[Si](C)(C)C(C)(C)C2284.7Standard polar33892256
Ureidopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C2029.9Semi standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C1970.3Standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCN(C(N)=O)[Si](C)(C)C(C)(C)C2477.1Standard polar33892256
Ureidopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C2156.4Semi standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C1999.9Standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C(=O)NCCC(=O)O)[Si](C)(C)C(C)(C)C2282.3Standard polar33892256
Ureidopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C2138.6Semi standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C2002.2Standard non polar33892256
Ureidopropionic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C2263.9Standard polar33892256
Ureidopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2368.8Semi standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2207.1Standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2227.0Standard polar33892256
Ureidopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2333.2Semi standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2193.4Standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2242.2Standard polar33892256
Ureidopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2387.9Semi standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2311.4Standard non polar33892256
Ureidopropionic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2223.3Standard polar33892256
Ureidopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2615.6Semi standard non polar33892256
Ureidopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2520.6Standard non polar33892256
Ureidopropionic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2209.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized)splash10-002f-3910000000-bbd51b3bb30ff8d230d32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (1 TMS)splash10-00n0-5900000000-00dc280a63401c96ec2a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (3 TMS)splash10-0udi-2930000000-fcdce5cf4a20023c403a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (2 TMS)splash10-0hr0-2900000000-8a898fc59206b3f30a132014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized)splash10-002f-3910000000-bbd51b3bb30ff8d230d32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized)splash10-00n0-5900000000-00dc280a63401c96ec2a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized)splash10-0udi-2930000000-fcdce5cf4a20023c403a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized)splash10-0hr0-2900000000-8a898fc59206b3f30a132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-EI-TOF (Non-derivatized)splash10-0udj-1910000000-83ab1eb4328f8caae9932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ureidopropionic acid GC-EI-TOF (Non-derivatized)splash10-0v01-0900000000-aeacd84d8e0e914182322017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-f7cdf5fc49adf0b5e7262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9300000000-7b12845cd5bc4d02874c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ureidopropionic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00r6-9500000000-7ea8c95e3dc6296a07e92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-9100000000-7b61b087fbf6c821bdd02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0596-9200000000-79dfb7a1a6838745e1782012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid , positive-QTOFsplash10-014l-8900000000-9bfe2297b9071d10d7e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 0V, negative-QTOFsplash10-001i-2900000000-e1e9196162c1cd0606e62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 0V, negative-QTOFsplash10-001r-5900000000-0e75c38978d4fd27ad1b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 0V, negative-QTOFsplash10-001r-8900000000-d71c6b65e5ea4a2b98a22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 0V, negative-QTOFsplash10-0019-9600000000-995ba80b11e5e2fdbed62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 1V, negative-QTOFsplash10-000i-9300000000-efa2833fbedc0d3bd7462020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 1V, negative-QTOFsplash10-000i-9200000000-92bf1d8bc142b2e065f42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 1V, negative-QTOFsplash10-000i-9100000000-e52a09e58825a4f43bbb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 1V, negative-QTOFsplash10-000i-9000000000-0a7fa362cd3cbcf815342020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 2V, negative-QTOFsplash10-000i-9000000000-88ef7f8836542c76d47b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 2V, negative-QTOFsplash10-000i-9000000000-223a7c6bd0e90d91dacf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 3V, negative-QTOFsplash10-000i-9000000000-eefd307fa9aedb8dbaaa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 4V, negative-QTOFsplash10-000i-9000000000-ae89b554e34311f8358b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid Orbitrap 5V, negative-QTOFsplash10-000i-9000000000-1cfc112d7baf56aa65ab2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid n/a 9V, negative-QTOFsplash10-000i-9100000000-97d06beb4575ef6147d72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ureidopropionic acid n/a 9V, negative-QTOFsplash10-0a4i-9000000000-08bac9ac1941233e516c2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 10V, Positive-QTOFsplash10-01b9-7900000000-684d9877d084bfc7c9552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 20V, Positive-QTOFsplash10-00dl-9100000000-0b6f9ea311703e9ecf132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 40V, Positive-QTOFsplash10-00b9-9000000000-1cb23a8265b8823133092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 10V, Negative-QTOFsplash10-001c-9300000000-2cec50bd5b226a288c822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 20V, Negative-QTOFsplash10-000f-9100000000-63ecd2f9ef02c677503d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ureidopropionic acid 40V, Negative-QTOFsplash10-0006-9000000000-396bc860a5f8f06ff7c52017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 0.5 uMChildren (1-13 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.23 (1.48 - 2.81) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.09 (1.23–4.80) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<3.2 umol/mmol creatinineInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.88 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0.0-1.0) uMChildren (1-13 years old)BothDihydropyrimidinase deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Dihydropyrimidinase deficiency
  1. van Kuilenburg AB, Meijer J, Dobritzsch D, Meinsma R, Duran M, Lohkamp B, Zoetekouw L, Abeling NG, van Tinteren HL, Bosch AM: Clinical, biochemical and genetic findings in two siblings with a dihydropyrimidinase deficiency. Mol Genet Metab. 2007 Jun;91(2):157-64. Epub 2007 Mar 26. [PubMed:17383919 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021879
KNApSAcK IDNot Available
Chemspider ID109
KEGG Compound IDC02642
BioCyc ID3-UREIDO-PROPIONATE
BiGG IDNot Available
Wikipedia Link3-Ureidopropionic_acid
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18261
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis Referencew-Ureido carboxylic acids. (1962), 3 pp. GB 913713 19621228 CAN 58:72975 AN 1963:72975
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:11675655 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Catalyzes the second step of the reductive pyrimidine degradation, the reversible hydrolytic ring opening of dihydropyrimidines. Can catalyze the ring opening of 5,6-dihydrouracil to N-carbamyl-alanine and of 5,6-dihydrothymine to N-carbamyl-amino isobutyrate.
Gene Name:
DPYS
Uniprot ID:
Q14117
Molecular weight:
56629.36
Reactions
Dihydrouracil + Water → Ureidopropionic aciddetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:
Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:
UPB1
Uniprot ID:
Q9UBR1
Molecular weight:
43165.705
Reactions
Ureidopropionic acid + Water → beta-Alanine + CO(2) + Ammoniadetails
Ureidopropionic acid + Water → beta-Alanine + Carbon dioxide + Ammoniadetails
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. [PubMed:11675655 ]
General function:
Involved in hydrolase activity
Specific function:
Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:
DPYSL3
Uniprot ID:
Q14195
Molecular weight:
61962.8
General function:
Nucleotide transport and metabolism
Specific function:
Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. Plays a role in axon guidance, neuronal growth cone collapse and cell migration
Gene Name:
DPYSL2
Uniprot ID:
Q16555
Molecular weight:
62293.1