3-(Uracil-1-yl)-L-alanine
Basic information
- CAS
21416-43-3- Standard SMILES
[NH3+][C@@H](Cn1ccc(=O)[nH]c1=O)C(=O)[O-]- InChIKey
FACUYWPMDKTVFU-BYPYZUCNSA-N- Molecular formula
- C7H9N3O4
- Average molar mass
- 199.16 g/mol
- Monoisotopic mass
- 199.05930578
Overview
3-(uracil-1-yl)-L-alanine zwitterion is zwitterionic form of 3-(uracil-1-yl)-L-alanine having an anionic carboxy group and a protonated amino group. It is a tautomer of a 3-(uracil-1-yl)-L-alanine.
Names & identifiers
- Preferred name
- 3-(Uracil-1-yl)-L-alanine
- IUPAC
- (2S)-2-azaniumyl-3-(2,4-dioxopyrimidin-1-yl)propanoate
- English name
- S(-)-alpha-amino-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
- Molecular formula
- C7H9N3O4
- Molecular weight
- 199.16
Names & synonyms
3-(Uracil-1-yl)-L-alanineCHEBI:575433-(uracil-1-yl)-L-alanine zwitterion(2S)-2-azaniumyl-3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate(2S)-2-azaniumyl-3-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)propanoatewillardiineC03584WillardineL-WILLARDIINE(-)-WILLARDIINES(-)-WILLARDIINES(-)-WILLARDIINE AMPA/KAINATE AGONIST
Show more names
3-[(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine)-1-yl]-L-alanineS(-)-α-Amino--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid
Database identifiers
- CAS
21416-43-3- PubChem CID
- 25200769
- ChEBI
CHEBI:57543
Properties
Computed structural properties
- XLogP
- -3.7
- Topological polar surface area
- 117 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 307
Physicochemical properties
- Melting point
- 204 · 204-205 °C
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- 0.1 M · 0.1 M NaOH: 7.2 mg/mL
- Density
- 1.501 · 1.501±0.06 g/cm3(Predicted)
- pka
- 2.12 · 2.12±0.10(Predicted)
- form
- solid
- color
- white
- FDA UNII
- 2 R4I0X4W9 · X2R4I0X4W9
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H332
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
Chemistry & industry
Applications
DescriptionThis 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].
Additional notes
DefinitionChEBI: 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.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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