| Identification | Back Directory | [Name]
S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID | [CAS]
21416-43-3 | [Synonyms]
C03584
Willardine
willardiine
L-WILLARDIINE
(-)-WILLARDIINE
S(-)-WILLARDIINE
3-(Uracil-1-yl)-L-alanine
S(-)-WILLARDIINE AMPA/KAINATE AGONIST
3-[(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine)-1-yl]-L-alanine
S(-)-α-Amino--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
S(-)-ALPHA-AMINO-3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINEPROPANOIC ACID
1(2H)-Pyrimidinepropanoic acid, α-amino-3,4-dihydro-2,4-dioxo-, (αS)-
(S)-2-Amino-3-[2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl]propanoic acid
(2S)-2-Amino-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-yl)propionic acid | [Molecular Formula]
C7H9N3O4 | [MDL Number]
MFCD00153879 | [MOL File]
21416-43-3.mol | [Molecular Weight]
199.16 |
| Chemical Properties | Back Directory | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
0.1 M NaOH: 7.2 mg/mL
| [density ]
1.501±0.06 g/cm3(Predicted) | [form ]
solid
| [pka]
2.12±0.10(Predicted) | [color ]
white
|
| Hazard Information | Back Directory | [Description]
This simple base occurs in germinatine pea seeds or seedlings. The structure
given above has been determined from chemical and s'pectroscopic analysis.
| [Uses]
(S)-Willardiine is a potent agonist of AMPA/kainate receptors with EC50 of 44.8 uM.
IC50 value: 44.8 uM(EC50) [1]
Target: AMPA/kainate receptor agonist
in vitro: The (S)- but not (R)-isomers of willardiine and 5-bromowillardiine were potent agonists, producing rapidly but incompletely desensitizing responses [1]. At a concentration of 1.8 mM, Ca2+ inhibited the currents induced by 100 microM willardiine by approximately 50% [2].
in vivo: In newborn mice (P5, histopathology at P10), local injection of the AMPA receptor agonist S-bromo-willardiine at day 5 after birth induced cortical damage and white matter damage, which was reduced in a dose-dependent manner by the AMPA receptor antagonists [3]. | [Definition]
ChEBI: 3-(uracil-1-yl)-L-alanine is the 3-(uracil-1-yl) derivative of L-alanine. It is a non-proteinogenic L-alpha-amino acid and a L-alanine derivative. It is functionally related to a uracil. It is a tautomer of a 3-(uracil-1-yl)-L-alanine zwitterion. | [IC 50]
Kainate Receptor | [References]
Ashworth, Brown, Roberts., Biochern J., 129,897 (1972) |
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