(4R)-4-carbamoyl-4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butanoic acid

• ChemBase ID: 176696
• Molecular Formular: C13H12N2O5
• Molecular Mass: 276.24478
• Monoisotopic Mass: 276.07462149
• SMILES: c1ccc2c(c1)C(=O)N(C2=O)[C@H](CCC(=O)O)C(=O)N
• Canonical SMILES: OC(=O)CC[C@@H](N1C(=O)c2c(C1=O)cccc2)C(=O)N
• InChI: InChI=1S/C13H12N2O5/c14-11(18)9(5-6-10(16)17)15-12(19)7-3-1-2-4-8(7)13(15)20/h1-4,9H,5-6H2,(H2,14,18)(H,16,17)/t9-/m1/s1
• InChIKey: CUBMYGDAHSAJPJ-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-carbamoyl-4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butanoic acid
• IUPAC Traditional name: (4R)-4-carbamoyl-4-(1,3-dioxoisoindol-2-yl)butanoic acid
• Synonyms: NSC 92155; (4R)-5-Amino-4-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)-5-oxopentanoic Acid; D-4-Phthalimido-glutaramic Acid

Database IDs

• CAS Number: 2614-09-7
• PubChem SID: 164232606
• PubChem CID: 260616

CALCULATED PROPERTIES

• Acid pKa: 3.643374
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.0497448
• LogD (pH = 7.4): -3.5236537
• Log P: -0.19624667
• Molar Refractivity: 67.4026 cm^3
• Polarizability: 25.236639 Å^3
• Polar Surface Area: 117.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - P384630

Thalidomide (T338850) derivative.

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)