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Record Information
Version3.6
Creation Date2013-05-17 01:20:39 UTC
Update Date2017-08-15 23:26:33 UTC
HMDB IDHMDB0060435
Secondary Accession Numbers
  • HMDB60435
Metabolite Identification
Common Namealpha-Fluoro-beta-ureidopropionic acid
Descriptionalpha-Fluoro-beta-ureidopropionic acid is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2-fluoro-3-Ureidopropionic acidKegg
2-fluoro-3-UreidopropionateGenerator
a-fluoro-b-UreidopropionateGenerator
a-fluoro-b-Ureidopropionic acidGenerator
alpha-fluoro-beta-UreidopropionateGenerator
α-fluoro-β-ureidopropionateGenerator
α-fluoro-β-ureidopropionic acidGenerator
FUPAMeSH
Chemical FormulaC4H7FN2O3
Average Molecular Weight150.1084
Monoisotopic Molecular Weight150.044070305
IUPAC Name2-fluoro-3-[(C-hydroxycarbonimidoyl)amino]propanoic acid
Traditional NameFUPA
CAS Registry NumberNot Available
SMILES
OC(=N)NCC(F)C(O)=O
InChI Identifier
InChI=1S/C4H7FN2O3/c5-2(3(8)9)1-7-4(6)10/h2H,1H2,(H,8,9)(H3,6,7,10)
InChI KeyFKTHAKABFGARQH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Carbonic acid derivative
  • Urea
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alkyl halide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
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
Water Solubility0.94 mg/mLALOGPS
logP-0.77ALOGPS
logP-2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.41 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity39.41 m3·mol-1ChemAxon
Polarizability12.14 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16631
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060435
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      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
      5,6-Dihydro-5-fluorouracil + Water → alpha-Fluoro-beta-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
      alpha-Fluoro-beta-ureidopropionic acid + Water → alpha-Fluoro-beta-alanine + Carbon dioxide + Ammoniadetails