3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)(2,3,4,5,6-13C5)piperidine-2,6-dione

• ChemBase ID: 172259
• Molecular Formular: C13H13N3O3
• Molecular Mass: 264.22389419
• Monoisotopic Mass: 264.11246548
• SMILES: c1cc(c2c(c1)C(=O)N(C2)[13CH]1[13C](=O)N[13C](=O)[13CH2][13CH2]1)N
• Canonical SMILES: O=[13C]1[13CH2][13CH2][13CH]([13C](=O)N1)N1Cc2c(C1=O)cccc2N
• InChI: InChI=1S/C13H13N3O3/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18/h1-3,10H,4-6,14H2,(H,15,17,18)/i4+1,5+1,10+1,11+1,12+1
• InChIKey: GOTYRUGSSMKFNF-GSUYAWNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)(2,3,4,5,6-^1^3C₅)piperidine-2,6-dione
• IUPAC Traditional name: 3-(4-amino-1-oxo-3H-isoindol-2-yl)(2,3,4,5,6-^1^3C₅)piperidine-2,6-dione
• Synonyms: 1-Oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline-13C5; CC-5013-13C5; rac Lenalidomide-13C5; 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione-13C5

Database IDs

• CAS Number: 1219332-91-8
• PubChem SID: 164228169
• PubChem CID: 46782050

CALCULATED PROPERTIES

• Acid pKa: 11.6131735
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.7081335
• LogD (pH = 7.4): -0.707882
• Log P: -0.7078522
• Molar Refractivity: 68.2981 cm^3
• Polarizability: 25.243994 Å^3
• Polar Surface Area: 92.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 248-250°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L328002

Labelled Lenalidomide (L328000). Immunomodulatory drug; analog of Thalidomide.

REFERENCES

• Bartlett, J.B., et al.: Nature Rev., 4, 314 (2004)
• Mitsiades, C.S., et al.: Curr. Opin. Invest. Drugs, 5, 635 (2004)
• List, A., et al.: N. Engl. J. Med., 352, 549 (2004)