benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 106661
• Molecular Formular: C30H35N5O4S
• Molecular Mass: 561.695
• Monoisotopic Mass: 561.24097563
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)SCc1ccccc1
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)SCc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C30H35N5O4S/c31-29(32)33-18-10-17-25(28(37)40-21-24-15-8-3-9-16-24)34-27(36)26(19-22-11-4-1-5-12-22)35-30(38)39-20-23-13-6-2-7-14-23/h1-9,11-16,25-26H,10,17-21H2,(H,34,36)(H,35,38)(H4,31,32,33)/t25-,26-/m0/s1
• InChIKey: OQHJASKXSKVOQO-UIOOFZCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: Z-Phe-Arg-Thiobenzyl Ester; Z-FR-Thiobenzyl Ester; Z-Phe-Arg-Thiobenzyl Ester

Database IDs

• PubChem SID: 162105997
• PubChem CID: 25108807

CALCULATED PROPERTIES

• Acid pKa: 12.573143
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.8992747
• LogD (pH = 7.4): 1.9030446
• Log P: 4.00089
• Molar Refractivity: 167.2461 cm^3
• Polarizability: 60.89853 Å^3
• Polar Surface Area: 146.4 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

REFERENCES

• McRae, B. J. et al., Biochem., 20:7196 (1981).