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

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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

Average Mass

217.15450

Monoisotopic Mass

217.04988

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 base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) 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.

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

Last Modified

28 November 2014