EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:42549 - 3-(5-fluorouracil-1-yl)-L-alanine

ChEBI IDCHEBI:42549
ChEBI Name3-(5-fluorouracil-1-yl)-L-alanine
Stars
ASCII Name3-(5-fluorouracil-1-yl)-L-alanine
DefinitionAn alanine derivative that is L-alanine bearing a 5-fluorouracil-1-yl substituent at position 3. A more potent and selective AMPA receptor agonist (at hGluR1 and hGluR2) than AMPA itself (Ki = 14.7, 25.1, and 1820 nM for hGluR1, hGluR2 and hGluR5 respectively).
Last Modified28 November 2014
DownloadsMolfile
FormulaC7H8FN3O4
Net Charge0
Average Mass217.156
Monoisotopic Mass217.04988
SMILESN[C@@H](Cn1cc(F)c(=O)nc1=O)C(=O)O
InChIInChI=1S/C7H8FN3O4/c8-3-1-11(2-4(9)6(13)14)7(15)10-5(3)12/h1,4H,2,9H2,(H,13,14)(H,10,12,15)/t4-/m0/s1
InChIKeyDBWPFHJYSTVBCZ-BYPYZUCNSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
AMPA receptor agonist  An agonist that selectively binds to and activates AMPA receptors.
ChEBI Ontology
Outgoing Relation(s)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) has functional parent uracil (CHEBI:17568)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) has role AMPA receptor agonist (CHEBI:64102)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) is a L-alanine derivative (CHEBI:83943)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
3-(5-fluorouracil-1-yl)-L-alanine (CHEBI:42549) is a organofluorine compound (CHEBI:37143)
IUPAC Name 
3-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-L-alanine
Synonyms  Source
2-AMINO-3-(5-FLUORO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-PROPIONIC ACIDPDBeChem
(S)-(−)-5-fluorowillardiineChEBI
(S)-F-WillardiineKEGG COMPOUND
5-FluorowillardiineChemIDplus
(S)-alpha-Amino-5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimmidinepropanoic acidChemIDplus
(2S)-2-amino-3-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanoic acidDrugBank
Manual XrefsDatabases
FWDPDBeChem
C13671KEGG COMPOUND
5-FluorowillardiineWikipedia
DB02966DrugBank
Registry NumbersSources
Reaxys:7817206Reaxys
CAS:140187-23-1ChemIDplus
Citations