(4S)-5-(benzyloxy)-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid

• ChemBase ID: 163649
• Molecular Formular: C20H21NO6
• Molecular Mass: 371.38384
• Monoisotopic Mass: 371.1368874
• SMILES: C(C[C@H](NC(=O)OCc1ccccc1)C(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)OCc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C20H21NO6/c22-18(23)12-11-17(19(24)26-13-15-7-3-1-4-8-15)21-20(25)27-14-16-9-5-2-6-10-16/h1-10,17H,11-14H2,(H,21,25)(H,22,23)/t17-/m0/s1
• InChIKey: VWHKODOUMSMUAF-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-(benzyloxy)-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-5-(benzyloxy)-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid
• Synonyms: N-[(Phenylmethoxy)carbonyl]-L-glutamic Acid 1-(Phenylmethyl)ester; N-(Benzyloxycarbonyl)-L-glutamic Acid α-Benzyl Ester; N-Benzyloxycarbonyl-L-glutamic Acid 1-Benzyl Ester; NSC 169160; α-Benzyl N-(benzyloxycarbonyl)-L-glutamate; N-Carbobenzyloxy-L-glutamic Acid O-Benzyl Ester

Database IDs

• CAS Number: 3705-42-8
• PubChem SID: 162257784
• PubChem CID: 6994031

CALCULATED PROPERTIES

• Acid pKa: 3.9137948
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.5087143
• LogD (pH = 7.4): -0.105294175
• Log P: 3.101116
• Molar Refractivity: 96.3494 cm^3
• Polarizability: 37.865612 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 92-93°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C176515

A new glutamate analogue as potential neuroprotective agent.

REFERENCES

• Takahashi, M., et al.: J. Exp. Biol., 200, 401 (1997)
• Michaelis, E., et al.: Prog. Neurobiol., 54, 369 (1997)
• Koch, H., et al.: Mol. Pharmacol., 55, 1044 (1997)
• O'Kane, R., et al.: J. Biol. Chem., 274, 31891 (1997)