GABAReceptorInhibitorgabareceptorinhibitor

Ureidopropionic acid

By rofalproject
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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 3-[(Aminocarbonyl)amino]propanoic acidChEBI 3-UreidopropanoateChEBI 3-Ureidopropanoic acidChEBI 3-UreidopropionateChEBI 3-Ureidopropionic acidChEBI beta-Ureidopropionic acidChEBI N-(AMINOCARBONYL)-BETA-alanineChEBI Ureidopropanoic acidChEBI 3-[(Aminocarbonyl)amino]propanoateGenerator UreidopropionateGenerator b-UreidopropionateGenerator b-Ureidopropionic acidGenerator beta-UreidopropionateGenerator β-ureidopropionateGenerator β-ureidopropionic acidGenerator N-(AMINOCARBONYL)-b-alanineGenerator N-(AMINOCARBONYL)-β-alanineGenerator UreidopropanoateGenerator 3-(carbamoylamino)PropanoateHMDB 3-(carbamoylamino)Propanoic acidHMDB 3-ureido-PropionateHMDB Carbamoyl-b-ala-OHHMDB Carbamoyl-beta-ala-OHHMDB N-(Aminocarbonyl)-'b-alanineHMDB N-Carbamoyl-b-alanineHMDB N-Carbamoyl-beta-alanineHMDB N-Carbamyl-b-alanineHMDB N-Carbamyl-beta-alanineHMDB Ion(-1) OF N-carbamoyl-beta-alanineMeSH

Chemical Formlia

C4H8N2O3 Average Molecliar Weight

132.1179 Monoisotopic Molecliar Weight

132.053492132 IUPAC Name

3-(carbamoylamino)propanoic acid Traditional Name

ureidopropionic acid CAS Registry Number

462-88-4 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 Key

JSJWCHRYRHKBBW-UHFFFAOYSA-N Chemical Taxonomy Description

This 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 Class

Organic compounds Class

Organic acids and derivatives Sub Class

Organic carbonic acids and derivatives Direct Parent

Ureas Alternative Parents

  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • beta-alanine derivative (CHEBI:18261 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

  • Component of Pantothenate and CoA biosynthesis
  • Component of Pyrimidine metabolism
  • Component of beta-Alanine metabolism

    • Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point170 °CNot Available Boiling PointNot AvailableNot Available Water Solubility20.9 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-MSsplash10-002f-3910000000-bbd51b3bb30ff8d230d3View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (1 TMS)splash10-00n0-5900000000-00dc280a63401c96ec2aView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (3 TMS)splash10-0udi-2930000000-fcdce5cf4a20023c403aView in MoNA GC-MS

    GC-MS Spectrum – GC-MS (2 TMS)splash10-0hr0-2900000000-8a898fc59206b3f30a13View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0udj-1910000000-83ab1eb4328f8caae993View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0udj-1910000000-83ab1eb4328f8caae993View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-0v01-0900000000-aeacd84d8e0e91418232View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00r6-9500000000-7ea8c95e3dc6296a07e9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9100000000-7b61b087fbf6c821bdd0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0596-9200000000-79dfb7a1a6838745e178View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-014l-8900000000-9bfe2297b9071d10d7e5View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Beta Ureidopropionase DeficiencySMP00172Not Available Beta-Alanine MetabolismSMP00007map00410 Carnosinuria, carnosinemiaSMP00493Not Available Dihydropyrimidinase DeficiencySMP00178Not Available GABA-Transaminase DeficiencySMP00351Not Available MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)SMP00202Not Available Pyrimidine MetabolismSMP00046map00240 UMP Synthase Deiciency (Orotic Aciduria)SMP00219Not Available Ureidopropionase deficiencySMP00492Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot Available

    Normal

  • details Cerebrospinal Fluid (CSF)Detected and Quantified0.0 – 0.5 uMChildren (1-13 years old)Not SpecifiedNormal

  • 17383919

    • details UrineDetected and Quantified2.23 (1.48 – 2.81) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 16513432

    • details UrineDetected and Quantified2.09 (1.23–4.80) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 12798197

    • details UrineDetected and Quantified0.88 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 12798197

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Cerebrospinal Fluid (CSF)Detected and Quantified0.5 (0.0-1.0) uMChildren (1-13 years old)BothDihydropyrimidinase deficiency

  • 17383919

    • 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 ]

    Associated OMIM IDs

  • 222748 (Dihydropyrimidinase deficiency)

    • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB021879 KNApSAcK ID

    Not Available Chemspider ID

    109 KEGG Compound ID

    C02642 BioCyc ID

    3-UREIDO-PROPIONATE BiGG ID

    40270 Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00026 Metagene Link

    HMDB00026 METLIN ID

    5097 PubChem Compound

    111 PDB ID

    URP ChEBI ID

    18261

    Product: Dihydroergotoxine (mesylate)

    References 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) 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 ]

    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 acid details
    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) + Ammonia details Ureidopropionic acid + Water → Beta-Alanine + Carbon dioxide + Ammonia details
    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

    PMID: 12489786

    By rofalproject

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