(2R,3S)-3-(carboxymethyl)azetidine-2-carboxylic acid

• ChemBase ID: 163702
• Molecular Formular: C6H9NO4
• Molecular Mass: 159.13996
• Monoisotopic Mass: 159.05315777
• SMILES: N1[C@H]([C@H](C1)CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@H]1CN[C@H]1C(=O)O
• InChI: InChI=1S/C6H9NO4/c8-4(9)1-3-2-7-5(3)6(10)11/h3,5,7H,1-2H2,(H,8,9)(H,10,11)/t3-,5+/m0/s1
• InChIKey: FQUPICCTRPWMDZ-WVZVXSGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-3-(carboxymethyl)azetidine-2-carboxylic acid
• IUPAC Traditional name: (2R,3S)-3-(carboxymethyl)azetidine-2-carboxylic acid
• Synonyms: (2S-trans)-2-Carboxy-3-azetidineacetic Acid; (2S,3S)-trans-3-(Carboxymethyl)-azetidine-2-acetic Acid

Database IDs

• CAS Number: 185387-36-4
• PubChem SID: 162257837
• PubChem CID: 12184172

CALCULATED PROPERTIES

• Acid pKa: 1.3244687
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.873288
• LogD (pH = 7.4): -6.566265
• Log P: -3.5206914
• Molar Refractivity: 34.1025 cm^3
• Polarizability: 13.802411 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C179850

A potent KA receptor agonist (0.7uM) as well as a potent inhibitor of Sodium dependent glu uptake (5uM).

REFERENCES

• Kozikowski, A., et al.: Bioorganic & Med. Chem. Letters, 6, 21, 2559 (1996)