(2S,4R)-pyrrolidine-2,4-dicarboxylic acid

• ChemBase ID: 105081
• Molecular Formular: C6H9NO4
• Molecular Mass: 159.13996
• Monoisotopic Mass: 159.05315777
• SMILES: O=C(O)[C@H]1NC[C@H](C(=O)O)C1
• Canonical SMILES: OC(=O)[C@H]1NC[C@@H](C1)C(=O)O
• InChI: InChI=1S/C6H9NO4/c8-5(9)3-1-4(6(10)11)7-2-3/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4+/m1/s1
• InChIKey: NRSBQSJHFYZIPH-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-pyrrolidine-2,4-dicarboxylic acid
• IUPAC Traditional name: (2S,4R)-pyrrolidine-2,4-dicarboxylic acid
• Synonyms: L-trans-PYRROLIDINE-2,4-DICARBOXYLIC ACID; trans-4-Carboxy-L-proline; L-trans-Pyrrolidine-2,4-dicarboxylic acid

Database IDs

• CAS Number: 64769-66-0
• MDL Number: MFCD00153866
• PubChem SID: 162093274; 24898859
• PubChem CID: 1515192

CALCULATED PROPERTIES

• Acid pKa: 1.3770988
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -5.1619215
• LogD (pH = 7.4): -6.559184
• Log P: -3.2760243
• Molar Refractivity: 34.1502 cm^3
• Polarizability: 13.802411 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: rat ... Gria1(50592), Grik1(29559), Grin2a(24409), Slc1a2(29482), Slc1a3(29483)

Product Information

• Purity: ≥98%; 98%

DETAILS

MP Biomedicals - 02158544

Purity: 98%
Selectively and potently inhibits the uptake of glutamate.

Sigma Aldrich - P7575

Biochem/physiol Actions
Selective inhibitor of glutamate uptake

REFERENCES

• Bridges, R.J., et al., J. Med. Chem., 34: 717 (1991).
• Balcar, V.J., et al., FEBS Lett., 300: 203 (1992).