(4R)-4-{[(benzyloxy)carbonyl]amino}-4-carbamoylbutanoic acid

• ChemBase ID: 163686
• Molecular Formular: C13H16N2O5
• Molecular Mass: 280.27654
• Monoisotopic Mass: 280.10592162
• SMILES: C(C[C@H](C(=O)N)NC(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(N[C@@H](C(=O)N)CCC(=O)O)OCc1ccccc1
• InChI: InChI=1S/C13H16N2O5/c14-12(18)10(6-7-11(16)17)15-13(19)20-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,18)(H,15,19)(H,16,17)/t10-/m1/s1
• InChIKey: NHFBOIIKTDKSRE-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-{[(benzyloxy)carbonyl]amino}-4-carbamoylbutanoic acid
• IUPAC Traditional name: (4R)-4-{[(benzyloxy)carbonyl]amino}-4-carbamoylbutanoic acid
• Synonyms: (4R)-5-Amino-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]-pentanoic Acid; (R)-5-Amino-5-oxo-4-[[(phenylmethoxy)carbonyl]amino]-pentanoic Acid; NSC 92153; D-4-(Carboxyamino)-glutaramic Acid 4-Benzyl Ester

Database IDs

• CAS Number: 19522-39-5
• PubChem SID: 162257821
• PubChem CID: 14284195

CALCULATED PROPERTIES

• Acid pKa: 3.9348762
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.1482916
• LogD (pH = 7.4): -2.771418
• Log P: 0.42380622
• Molar Refractivity: 68.7899 cm^3
• Polarizability: 26.947578 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C177750

Used in the synthesis of Cbz-aminoglutarimides and Cbz-succinimides, for their anticonvulsant activity.

REFERENCES

• Park, M. et al.: Bioorgan. Med. Chem. Lett. 6, 1297 (1996)
• Lee, J. et al.: Arch. Pharm. Res. 19, 248 (1996)