2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro(2H4)-1H-isoindole-1,3-dione

• ChemBase ID: 178488
• Molecular Formular: C13H10N2O4
• Molecular Mass: 258.2295
• Monoisotopic Mass: 258.06405681
• SMILES: c1cccc2c1C(=O)N(C2=O)C1C(=O)NC(=O)CC1
• Canonical SMILES: O=C1CCC(C(=O)N1)N1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
• InChIKey: UEJJHQNACJXSKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro(^2H₄)-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(2,6-dioxopiperidin-3-yl)(^2H₄)isoindole-1,3-dione
• Synonyms: 2-(2,6-Dioxo-3-piperidinyl)-1H-iso-indole-1,3(2H)-dione-d4; α-Phthalimidoglutarimide-d4; 3-Phthalimidoglutarimide-d4; Celgene-d4; Contergan-d4; Distaval-d4; K 17-d4; Kevadon-d4; Myrin-d4; N-(2,6-Dioxo-3-piperidyl)phthalimide-d4; NSC 527179-d4; NSC 66847-d4; Thalidomide-d4

Database IDs

• CAS Number: 1219177-18-0
• PubChem SID: 164234398
• PubChem CID: 45040511

CALCULATED PROPERTIES

• Acid pKa: 11.593279
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.01570701
• LogD (pH = 7.4): 0.015679834
• Log P: 0.015707357
• Molar Refractivity: 64.3248 cm^3
• Polarizability: 24.035646 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Beige Solid
• Melting Point: 272-274°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T338852

Labelled Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.

REFERENCES

• D’Amato, r.J., et al.: Proc. Natl. Acad. Sci. USA, 91, 4082 (1994)
• Makonkawkeyoon, S., et al.: Proc. Natl. Acad. Sci. USA, 90, 5974 (1994)
• Schumacher, H., et al.: J. Pharmacol. Exp. Therap., 160, 189 (1968)