Structure via PubChem · Public domain (PubChem)
5-Fluorowillardiine
Sign in to saveAlso known as (2S)-2-amino-3-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanoic acid, (S)-alpha-Amino-5-fluoro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimmidinepropanoic acid, (S)-F-Willardiine, (S)-(-)-5-fluorowillardiine
5-Fluorowillardiine is a selective agonist for the AMPA receptor, with only limited effects at the kainate receptor. It is an excitotoxic neurotoxin when used in vivo and so is rarely used in intact animals, but it is widely used to selectively stimulate AMPA receptors in vitro. It is structurally similar to the compound willardiine, which is also an agonist for the AMPA and kainate receptors. Willardiine occurs naturally in Mariosousa willardiana and Acacia sensu lato.
Chemical data
- Formula
- C7H8FN3O4
- Molecular weight
- 217.15 g/mol
- IUPAC name
- (2S)-2-amino-3-(5-fluoro-2,4-dioxopyrimidin-1-yl)propanoic acid
- SMILES
- C1=C(C(=O)NC(=O)N1C[C@@H](C(=O)O)N)F
- InChIKey
- DBWPFHJYSTVBCZ-BYPYZUCNSA-N
- XLogP
- -4.4
- Polar surface area
- 113 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 217.05
Show 4 more facts
- Commons category
- 5-Fluorowillardiine
- chemical formula
- C₇H₈FN₃O₄
- canonical SMILES
- C1=C(C(=O)NC(=O)N1CC(C(=O)O)N)F
- isomeric SMILES
- C1=C(C(=O)NC(=O)N1C[C@@H](C(=O)O)N)F
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Toxicity
- Applications in research
- Chemistry
- Structure and activity
- Synthesis
- References
- External links
5-Fluorowillardiine is a selective agonist for the AMPA receptor, with only limited effects at the kainate receptor. It is an excitotoxic neurotoxin when used in vivo and so is rarely used in intact animals, but it is widely used to selectively stimulate AMPA receptors in vitro. It is structurally similar to the compound willardiine, which is also an agonist for the AMPA and kainate receptors. Willardiine occurs naturally in Mariosousa willardiana and Acacia sensu lato.
The name is unusual as it has two successive i's. This is not a typo.
Excerpted from Wikipedia’s “5-Fluorowillardiine” article, available under the CC BY-SA 4.0 licence.