(2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid hydrate

• ChemBase ID: 133188
• Molecular Formular: C10H17NO5
• Molecular Mass: 231.24568
• Monoisotopic Mass: 231.11067265
• SMILES: CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O.O
• Canonical SMILES: OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)C(=C)C.O
• InChI: InChI=1S/C10H15NO4.H2O/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13;/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15);1H2/t6-,7+,9-;/m0./s1
• InChIKey: FZNZRJRSYLQHLT-SLGZUKMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid hydrate
• IUPAC Traditional name: kainic acid hydrate
• Synonyms: 2-Carboxy-3-carboxymethyl-4-isopropenylpyrrolidine; Kainic acid monohydrate

Database IDs

• CAS Number: 58002-62-3
• MDL Number: MFCD00150833
• PubChem SID: 24724520; 162227465; 24277985
• PubChem CID: 11954253

CALCULATED PROPERTIES

• Acid pKa: 1.7361971
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.3863163
• LogD (pH = 7.4): -5.153439
• Log P: -2.3627985
• Molar Refractivity: 52.201 cm^3
• Polarizability: 20.809425 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL; H2O: soluble
• Apperance: white

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901), SLC1A1(6505), SLC1A2(6506), SLC1A3(6507)mouse ... Gria1(14799)rat ... Gria1(50592), Grik1(29559), Grik4(24406), Grin2a(24409)

Product Information

• Purity: ≥98% (HPLC); ≥99% (TLC)
• Impurities: Glutamate, free
• Biological Source: from Digenea simplex
• Empirical Formula (Hill Notation): C10H15NO4 · H2O

DETAILS

Sigma Aldrich - K0250

Application
Kainic acid is used to study mechanisms of excitation-induced apoptosis and epilepsy.
General description
Kainic acid is an agonist for kainate-class ionotropic glutamate receptors. Kainate receptors directly gate ion channels and are generally excitatory. Excess stimulation by Kainic acid induces neurocytosis (apoptosis) and epileptic seizures.
Preparation Note
Dissolve in 1-2 drops of 1N NaOH then bring to volume with water or aqueous buffer. Can be stored 1-2 days refrigerated.
Biochem/physiol Actions
Kainic acid monohydrate is an agonist at the kainate class of ionotropic glutamate receptors, which induces seizures and neurodegeneration in vivo and is used to induce experimental epilepsy in rodents and study the mechanisms of excitation-induced neuronal apoptosis.

Sigma Aldrich - K2389

Biochem/physiol Actions
Kainic acid monohydrate is an agonist at the kainate class of ionotropic glutamate receptors, which induces seizures and neurodegeneration in vivo and is used to induce experimental epilepsy in rodents and study the mechanisms of excitation-induced neuronal apoptosis.