(2S,3S,4R)-3-(carboxymethyl)-4-(propan-2-yl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 134348
• Molecular Formular: C10H17NO4
• Molecular Mass: 215.24628
• Monoisotopic Mass: 215.11575803
• SMILES: CC(C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)C(C)C
• InChI: InChI=1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
• InChIKey: JQPDCKOQOOQUSC-OOZYFLPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R)-3-(carboxymethyl)-4-(propan-2-yl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: dihydrokainate
• Synonyms: 2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid; Dihydrokainic acid

Database IDs

• CAS Number: 52497-36-6
• MDL Number: MFCD03412037
• PubChem SID: 24277981; 162228624
• PubChem CID: 107883

CALCULATED PROPERTIES

• Acid pKa: 1.7927866
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.9902804
• LogD (pH = 7.4): -4.7623477
• Log P: -2.016102
• Molar Refractivity: 52.4235 cm^3
• Polarizability: 21.059736 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
• Apperance: powder

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: human ... SLC1A1(6505), SLC1A2(6506), SLC1A3(6507)rat ... Slc1a2(29482), Slc1a3(29483)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - D1064

Biochem/physiol Actions
Dihydrokainic acid is a selective inhibitor of the GLT-1 glutamate transporter. At higher concentrations, dihydrokainate is a weak inhibitor of AMPA/kainate glutamic acid receptors.