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Record Information
Version3.6
Creation Date2013-05-17 01:20:39 UTC
Update Date2017-03-02 22:05:04 UTC
HMDB IDHMDB60435
Secondary Accession NumbersNone
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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 LinkHMDB60435
Metagene LinkHMDB60435
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, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [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