benzyl N-{2-[(2S)-2-[(benzylsulfanyl)carbonyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate

• ChemBase ID: 106663
• Molecular Formular: C22H24N2O4S
• Molecular Mass: 412.50196
• Monoisotopic Mass: 412.14567826
• SMILES: O=C(NCC(=O)N1CCC[C@H]1C(=O)SCc1ccccc1)OCc1ccccc1
• Canonical SMILES: O=C(NCC(=O)N1CCC[C@H]1C(=O)SCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C22H24N2O4S/c25-20(14-23-22(27)28-15-17-8-3-1-4-9-17)24-13-7-12-19(24)21(26)29-16-18-10-5-2-6-11-18/h1-6,8-11,19H,7,12-16H2,(H,23,27)/t19-/m0/s1
• InChIKey: MOUXTJZLPNOSSQ-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{2-[(2S)-2-[(benzylsulfanyl)carbonyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate
• IUPAC Traditional name: benzyl N-{2-[(2S)-2-[(benzylsulfanyl)carbonyl]pyrrolidin-1-yl]-2-oxoethyl}carbamate
• Synonyms: Z-Gly-Pro-Thiobenzyl Ester; Z-GP-Thiobenzyl Ester; Z-Gly-Pro-Thiobenzyl Ester

Database IDs

• PubChem SID: 162106032
• PubChem CID: 25108809

CALCULATED PROPERTIES

• Acid pKa: 13.430225
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2725005
• LogD (pH = 7.4): 3.2725003
• Log P: 3.2725005
• Molar Refractivity: 112.3965 cm^3
• Polarizability: 43.897842 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

REFERENCES

• Smyth, M.J. et al., J. Biol. Chem., 267(34):24418 (1992).
• Velotti, F. et al., Eur. J. Imm., 22:1049 (1992).