3-(4-nitro-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione

• ChemBase ID: 59528
• Molecular Formular: C13H11N3O5
• Molecular Mass: 289.24354
• Monoisotopic Mass: 289.06987047
• SMILES: c1cc(c2c(c1)C(=O)N(C2)C1CCC(=O)NC1=O)[N+](=O)[O-]
• Canonical SMILES: O=C1CCC(C(=O)N1)N1Cc2c(C1=O)cccc2[N+](=O)[O-]
• InChI: InChI=1S/C13H11N3O5/c17-11-5-4-10(12(18)14-11)15-6-8-7(13(15)19)2-1-3-9(8)16(20)21/h1-3,10H,4-6H2,(H,14,17,18)
• InChIKey: JKPJLYIGKKDZDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-nitro-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione
• IUPAC Traditional name: 3-(4-nitro-1-oxo-3H-isoindol-2-yl)piperidine-2,6-dione
• Synonyms: 4-Nitro Lenalidomide; 3-(1,3-Dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione; 3-(4-Nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione; 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione; 3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione; (3S)-3-(4-Nitro-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione

Database IDs

• CAS Number: 827026-45-9
• MDL Number: MFCD18064658
• PubChem SID: 162064291
• PubChem CID: 11471781

CALCULATED PROPERTIES

• Acid pKa: 11.60593
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.061057586
• LogD (pH = 7.4): 0.061031256
• Log P: 0.061057985
• Molar Refractivity: 70.9224 cm^3
• Polarizability: 26.092962 Å^3
• Polar Surface Area: 112.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

DETAILS

Toronto Research Chemicals - N496395

Lenalidomide (L328000) analog. Lenalidomide impurity.

REFERENCES

• Hashimoto, Y., et al.: Bioorg. Med. Chem., 10, 461 (2002)