(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid

• ChemBase ID: 2707
• Molecular Formular: C5H7N3O5
• Molecular Mass: 189.12618
• Monoisotopic Mass: 189.03857034
• SMILES: N[C@@H](Cn1oc(=O)[nH]c1=O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cn1oc(=O)[nH]c1=O)N
• InChI: InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
• InChIKey: ASNFTDCKZKHJSW-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
• IUPAC Traditional name: quisqualate; @quisqualate
• Synonyms: Quisqualic acid; 3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine; Quisqualic acid; β-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine; Quisqualate; β-(3,5-二氧代-1,2,4-氧杂重氮烷-2-基)-L-丙氨酸; 使君子氨酸

Database IDs

• CAS Number: 52809-07-1
• MDL Number: MFCD00069337
• Beilstein Number: 1078734
• PubChem SID: 24278004; 46509075; 160966156
• PubChem CID: 40539
• CHEMBL: 279956
• Chemspider ID: 37038
• DrugBank ID: DB02999
• IUPHAR ligand ID: 1372
• KEGG ID: C08296
• MeSH Name: Quisqualic+Acid
• Wikipedia Title: Quisqualic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.455519
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.7313128
• LogD (pH = 7.4): -4.676513
• Log P: -3.6865237
• Molar Refractivity: 36.5118 cm^3
• Polarizability: 14.785922 Å^3
• Polar Surface Area: 121.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.69
• LOG S: -0.55
• Solubility (Water): 5.36e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble1.4 mg/mL; 1 M NH4OH: soluble20 mg/mL; 1 M NH4OH: soluble20 mg/mL, clear, colorless; ethanol: <0.17 mg/mL; H2O: soluble0.5 mg/mL; organic solvents: insoluble
• Apperance: white to off-white powder
• Melting Point: 187 - 188°C dec.

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418)

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C5H7N3O5

DETAILS

DrugBank - DB02999

• Drug Groups: experimental
• Description: An agonist at two subsets of excitatory amino acid receptors, ionotropic receptors that directly control membrane channels and metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores. The compound is obtained from the seeds and fruit of Quisqualis chinensis. [PubChem]

Sigma Aldrich - Q2128

Biochem/physiol Actions
Active enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors.

Sigma Aldrich - 83385

Biochem/physiol Actions
Active enantiomer of quisqualic acid; excitatory amino acid at glutamate receptors.
Other Notes
Quisqualate receptor agonist. In studies on excitatory amino acid receptors1,2