benzyl 2-{[1-(2-methoxy-2-oxoacetyl)pyrrolidin-2-yl]formamido}-3-phenylpropanoate

• ChemBase ID: 105313
• Molecular Formular: C24H26N2O6
• Molecular Mass: 438.47304
• Monoisotopic Mass: 438.17908656
• SMILES: COC(=O)C(=O)N1CCCC1C(=O)NC(Cc1ccccc1)C(=O)OCc1ccccc1
• Canonical SMILES: COC(=O)C(=O)N1CCCC1C(=O)NC(C(=O)OCc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C24H26N2O6/c1-31-24(30)22(28)26-14-8-13-20(26)21(27)25-19(15-17-9-4-2-5-10-17)23(29)32-16-18-11-6-3-7-12-18/h2-7,9-12,19-20H,8,13-16H2,1H3,(H,25,27)
• InChIKey: DQPXNIBWDJBVFH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-{[1-(2-methoxy-2-oxoacetyl)pyrrolidin-2-yl]formamido}-3-phenylpropanoate
• IUPAC Traditional name: benzyl 2-{[1-(2-methoxy-2-oxoacetyl)pyrrolidin-2-yl]formamido}-3-phenylpropanoate
• Synonyms: Harvard Peptide; N-CARBOMETHOXYCARBONYL-D-PRO-D-PHE BENZYL ESTER; N-CARBOMETHOXYCARBONYL-PRO-PHE BENZYL ESTER

Database IDs

• CAS Number: 129988-00-7
• PubChem SID: 162092320
• PubChem CID: 3979228

CALCULATED PROPERTIES

• Acid pKa: 12.107121
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8417969
• LogD (pH = 7.4): 2.8417895
• Log P: 2.8417969
• Molar Refractivity: 115.4923 cm^3
• Polarizability: 45.27247 Å^3
• Polar Surface Area: 102.01 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 125-128°C

Safety Information

• Storage Condition: 0°C

DETAILS

MP Biomedicals - 02159736

Blocks gp120 binding to CD4 glycoprotein and inhibits HIV infection, but is less active than the _D -isomer peptide.

MP Biomedicals - 02159735

Blocks gp120 binding to CD4 glycoprotein. Reported to inhibit infection by HIV.

REFERENCES

• Finberg, R.W., et al., Science , 249 : 287, (1990).
• Finberg, R. W., et al., Science , 249 : 287, (1990).