benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-4-carbamimidamidobutyl]carbamate

• ChemBase ID: 106659
• Molecular Formular: C27H38N8O4S
• Molecular Mass: 570.70682
• Monoisotopic Mass: 570.27367274
• SMILES: NC(=N)NCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)SCc1ccccc1
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)N[C@H](C(=O)SCc1ccccc1)CCCNC(=N)N)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C27H38N8O4S/c28-25(29)32-15-7-13-21(35-27(38)39-17-19-9-3-1-4-10-19)23(36)34-22(14-8-16-33-26(30)31)24(37)40-18-20-11-5-2-6-12-20/h1-6,9-12,21-22H,7-8,13-18H2,(H,34,36)(H,35,38)(H4,28,29,32)(H4,30,31,33)/t21-,22-/m0/s1
• InChIKey: IZOQULMMTIYGOZ-VXKWHMMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-4-carbamimidamidobutyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2S)-1-(benzylsulfanyl)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-4-carbamimidamidobutyl]carbamate
• Synonyms: Z-Arg-Arg-Thiobenzyl Ester; Z-RR-Thiobenzyl Ester; Z-Arg-Arg-Thiobenzyl Ester

Database IDs

• PubChem SID: 162105606
• PubChem CID: 25108805

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 12.64062
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -3.0827038
• LogD (pH = 7.4): -3.0752692
• Log P: 1.2406776
• Molar Refractivity: 176.0529 cm^3
• Polarizability: 59.862736 Å^3
• Polar Surface Area: 208.3 Å^2
• Rotatable Bonds: 18

DETAILS

MP Biomedicals - 03SB006

A colorimetric substrate for Cathepsin B.

REFERENCES

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