(3R,4R)-4-amino-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid

• ChemBase ID: 160371
• Molecular Formular: C10H20N2O3
• Molecular Mass: 216.2774
• Monoisotopic Mass: 216.14739251
• SMILES: N1(C(C[C@H]([C@H](C1(C)C)C(=O)O)N)(C)C)O
• Canonical SMILES: N[C@@H]1CC(C)(C)N(C([C@@H]1C(=O)O)(C)C)O
• InChI: InChI=1S/C10H20N2O3/c1-9(2)5-6(11)7(8(13)14)10(3,4)12(9)15/h6-7,15H,5,11H2,1-4H3,(H,13,14)/t6-,7+/m1/s1
• InChIKey: BCNGQKYGMSUIHK-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-4-amino-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid
• IUPAC Traditional name: (3R,4R)-4-amino-1-hydroxy-2,2,6,6-tetramethylpiperidine-3-carboxylic acid
• Synonyms: (3R,4R)-4-Amino-3-carboxy-2,2,6,6-tetramethyl-1-piperidinyloxy; (3R,4R)-4-Amino-1-oxyl-2,2,6,6-tetramethylpiperidine-3-carboxylic Acid

Database IDs

• CAS Number: 691364-99-5
• PubChem SID: 162254506
• PubChem CID: 46780320

CALCULATED PROPERTIES

• Acid pKa: 4.0617094
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.6372697
• LogD (pH = 7.4): -2.6252136
• Log P: -2.6250443
• Molar Refractivity: 55.9293 cm^3
• Polarizability: 22.634089 Å^3
• Polar Surface Area: 86.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A618875

The first spin-labelled, cyclic, chiral β-amino acid resolved in an enantiomerically pure state.

REFERENCES

• Konishi, M., et al.: J. Antibiot., 42, 1749 (1989)
• Tominaga, M., et al.: Chem. Pharm. Bull., 49, 1027 (1989)
• Steer, D., et al.: Curr. Med. Chem., 9, 811 (1989)