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

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ChEBI Name 3-(5-fluorouracil-1-yl)-L-alanine
ChEBI ID CHEBI:42549
ChEBI ASCII Name 3-(5-fluorouracil-1-yl)-L-alanine
Definition An 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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C7H8FN3O4
Net Charge 0
Average Mass 217.15450
InChI InChI=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
InChIKey DBWPFHJYSTVBCZ-BYPYZUCNSA-N
SMILES N[C@@H](Cn1cc(F)c(=O)[nH]c1=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): AMPA receptor agonist
An agonist that selectively binds to and activates AMPA receptors.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(2S)-2-amino-3-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanoic acid DrugBank
(S)-(−)-5-fluorowillardiine ChEBI
(S)-alpha-Amino-5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimmidinepropanoic acid ChemIDplus
(S)-F-Willardiine KEGG COMPOUND
2-AMINO-3-(5-FLUORO-2,4-DIOXO-3,4-DIHYDRO-2H-PYRIMIDIN-1-YL)-PROPIONIC ACID PDBeChem
5-Fluorowillardiine ChemIDplus
Database Links Databases
5-Fluorowillardiine Wikipedia
C13671 KEGG COMPOUND
DB02966 DrugBank
FWD PDBeChem
View more database links
Registry Numbers Types Sources
140187-23-1 CAS Registry Number ChemIDplus
7817206 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11041846 PubMed citation CiteXplore
11487516 PubMed citation CiteXplore
1371315 PubMed citation CiteXplore
16256076 PubMed citation CiteXplore
7566471 PubMed citation CiteXplore
8640342 PubMed citation CiteXplore
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Last Modified
28 November 2014