2-amino-2-(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)acetic acid hydrate

• ChemBase ID: 138821
• Molecular Formular: C5H8N2O5
• Molecular Mass: 176.12742
• Monoisotopic Mass: 176.04332137
• SMILES: c1c(o[nH]c1=O)C(C(=O)O)N.O
• Canonical SMILES: OC(=O)C(c1o[nH]c(=O)c1)N.O
• InChI: InChI=1S/C5H6N2O4.H2O/c6-4(5(9)10)2-1-3(8)7-11-2;/h1,4H,6H2,(H,7,8)(H,9,10);1H2
• InChIKey: QVKQQLYSTODTJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-(3-oxo-2,3-dihydro-1,2-oxazol-5-yl)acetic acid hydrate
• IUPAC Traditional name: ibotenic acid hydrate
• Synonyms: α-(3-Hydroxy-5-isoxazolyl)glycine; α-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid; α-Amino-3-hydroxy-5-isoxazoleacetic acid; Ibotenic acid monohydrate from Amanita sp.; α-(3-羟基-5-异噁唑基)甘氨酸; α-氨基-3-羟基-5-异噁唑乙酸; 鹅膏蕈氨酸; 鹅膏氨酸 一水合物 来源于鹅膏 属

Database IDs

• CAS Number: 60573-88-8
• MDL Number: MFCD00150903
• Beilstein Number: 1075440
• PubChem SID: 162233072; 24880352
• PubChem CID: 43362

CALCULATED PROPERTIES

• Acid pKa: 1.5552531
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.169774
• LogD (pH = 7.4): -4.810145
• Log P: -3.8928547
• Molar Refractivity: 33.9271 cm^3
• Polarizability: 13.147214 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble50 mg/mL, clear, colorless to yellow
• Melting Point: 148-151 °C

Safety Information

• RTECS: NY2100000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Purity: ≥99.0% (TLC); 97%
• Empirical Formula (Hill Notation): C5H6N2O4 · H2O

DETAILS

Sigma Aldrich - 56720

Other Notes
Review1; Studies on the glutamate receptor2
Biochem/physiol Actions
Ibotenic acid, a 3-isoxazolol amino acid, is an AMPA subtype glutamate receptor agonist involved in signal activation and blockade. Ibotenic acid from mushrooms such as Amanita muscaria and pantherina is an inducer of the “pantherina” central nervous system poisoning syndrome.
Ibotenic acid, a mushroom chemical neurotoxin, is used alone and together with factors such as β-amyloid(25-35) to induce neurotoxic lesions in the brain.