benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamate

• ChemBase ID: 106662
• Molecular Formular: C32H36N6O4S
• Molecular Mass: 600.73104
• Monoisotopic Mass: 600.25187466
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OCc1ccccc1)C(=O)SCc1ccccc1
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)SCc1ccccc1)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C32H36N6O4S/c33-31(34)35-17-9-16-27(30(40)43-21-23-12-5-2-6-13-23)37-29(39)28(18-24-19-36-26-15-8-7-14-25(24)26)38-32(41)42-20-22-10-3-1-4-11-22/h1-8,10-15,19,27-28,36H,9,16-18,20-21H2,(H,37,39)(H,38,41)(H4,33,34,35)/t27-,28-/m0/s1
• InChIKey: OOFJGEWERZZGIV-NSOVKSMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamate
• Synonyms: Z-Trp-Arg-Thiobenzyl Ester; Z-WR-Thiobenzyl Ester; Z-Trp-Arg-Thiobenzyl Ester

Database IDs

• PubChem SID: 162105608
• PubChem CID: 25108808

CALCULATED PROPERTIES

• Acid pKa: 12.609752
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 1.9980364
• LogD (pH = 7.4): 2.0017776
• Log P: 4.1044335
• Molar Refractivity: 178.3326 cm^3
• Polarizability: 66.09656 Å^3
• Polar Surface Area: 162.19 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

REFERENCES

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