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

• ChemBase编号: 2707
• 分子式: C5H7N3O5
• 平均质量: 189.12618
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
• IUPAC传统名: quisqualate; @quisqualate
• 别名: 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; 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

登记号

• CAS号: 52809-07-1
• MDL号: MFCD00069337
• Beilstein号: 1078734
• PubChem SID: 24278004; 46509075; 160966156
• PubChem CID: 40539
• CHEMBL: 279956
• Chemspider ID: 37038
• DrugBank ID: DB02999
• IUPHAR配体索引: 1372
• KEGG ID: C08296
• 医学主题词(MeSH): Quisqualic+Acid
• 维基百科标题: Quisqualic_acid

理论计算性质

JChem

• Acid pKa: 1.455519
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -3.7313128
• LogD (pH = 7.4): -4.676513
• Log P: -3.6865237
• 摩尔折射率: 36.5118 cm^3
• 极化性: 14.785922 Å^3
• 极化表面积: 121.96 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.69
• LOG S: -0.55
• 溶解度: 5.36e+01 g/l

分子性质

理化性质

• 溶解度: 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
• 外观: white to off-white powder
• 熔点: 187 - 188°C dec.

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418)

产品相关信息

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

详细说明

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