(S)-2-アミノ-3-(3,5-ジオキソテトラヒドロ-1,2,4-オキサジアゾール-2-イル)プロピオン酸
(αS)-α-アミノ-3,5-ジオキソテトラヒドロ-1,2,4-オキサジアゾール-2-プロピオン酸 · (αS)-α-アミノ-3,5-ジオキソ-1,2,4-オキサジアゾリジン-2-プロパン酸 · キスカル酸 · キスクアラート · (S)-2-アミノ-3-(3,5-ジオキソテトラヒドロ-1,2,4-オキサジアゾール-2-イル)プロピオン酸 · 3-(3,5-ジオキソ-1,2,4-オキサジアゾリジン-2-イル)-L-アラニン · (S)-2-アミノ-3-(3,5-ジオキソ-1,2,4-オキサジアゾリジン-2-イル)プロパン酸 · (αS)-α-アミノ-3,5-ジオキソ-1,2,4-オキサジアゾリジン-2-プロピオン酸
識別子と物理属性
| CAS No. | 52809-07-1 |
|---|---|
| 分子式 | C5H7N3O5 |
| 平均分子量 | 189.13 g/mol |
| 単同位体質量 | 189.03857032 g/mol |
| SMILES | N[C@@H](Cn1oc(=O)[nH]c1=O)C(=O)O |
| InChIKey | ASNFTDCKZKHJSW-REOHCLBHSA-N |
| PubChem CID | 40539 |
| ChEMBL | CHEMBL168279 |
| ChEBI | CHEBI:8734 |
| EC No. | 637-070-2 |
| DTXSID | DTXSID20896927 |
| 現地名 | (S)-2-アミノ-3-(3,5-ジオキソテトラヒドロ-1,2,4-オキサジアゾール-2-イル)プロピオン酸 |
化学・物理的性質
| XLogP | -3.9 |
|---|---|
| 極性表面積 | 122 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 3 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 265 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 融点 | 185-187°C dec. |
| 比旋光度 | D20 +17.0° (c = 2.0 in 6M HCl) |
| 沸点 | 324.36°C (rough estimate) |
| 密度 | 1.6649 (rough estimate) |
| 屈折率 | 1.6190 (estimate) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | NH4OH 1 M: 20 mg/mL、無色透明エタノール、水に可溶。有機溶剤に不溶。 |
| pKa（酸解離定数） | 2.12±0.10(Predicted) |
| 外観・状態 | 粉 |
| 色 | ホワイトからオフホワイト |
| Merck | 13,8177 |
| BRN | 1078734 |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| InChI | InChI=1/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-/s3 |
| InChIKey | ASNFTDCKZKHJSW-NVFNTWQMNA-N |
| SMILES | N1(C[C@H](N)C(=O)O)OC(=O)NC1=O |&1:2,r| |
化学的特性
Off-White Solid
安全性と法規制
| GHS 分類 | WarningH302+H312+H332 (41.2%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 68 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| F | 10 |
| 水環境危害等級（WGK） | 3 |
| 危険文句（R） | 20/21/22 |
| 危険表示 | Xn |
| 安全措置（S） | 26-36 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
L-Quisqualic acid is a natural analog of glutamate that acts as an agonist at AMPA-selective and metabotropic glutamate receptors (EC50s = 170, 10, 40, and 29 nM at GluR-A, mGluR1, mGluR3, and mGluR5, respectively), as well as the ionotropic kainate receptor (GRIK4; Ki = 6.43 nM). L-Quisqualic acid is used to study receptor dynamics and as an excitotoxin to selectively destroy neurons in the brain or spinal cord.
使用
Quisqualic acid is used to differentiate between mGluR-1 and mGluR-4. L-Quisqualic acid is an activator of GluR.
一般的な説明
Quisqualate/ Quisqualic acid is obtained from the fruits and seeds of Quisqualis chinensis. It is an agonist at two subsets of excitatory amino acid receptors metabotropic receptors that indirectly mediate calcium mobilization from intracellular stores and, ionotropic receptors that directly control membrane channels. L-quisqualic acid is an agonist of the neurotransmitter L-glutamate.
製法・合成法
純化方法
It has been purified by ion-exchange chromatography on Dowex 50W (x 8, H+ form); the desired fractions are lyophilised and recrystallised from H2O/EtOH. It has IR (KBr) : 3400-2750br, 1830s, 1775s, 1745s and 1605s cm-1;maxand 1H NMR (NaOD/D2O, pH 13) : 3.55-3.57 (1H m, X of ABX, H-2), 3.72-3.85 (2H, AB of ABX, H-3), 1 3C NMR (D2O) : 50.1t, 53.4d, 154.8s, 159.7s and 171.3s. [Baldwin et al. J Chem Soc, Chem Commun 256 1985.] It is a quasiqualate receptor agonist [Joels et al. Proc Natl Acad Sci USA 86 3404 1989].