benzyl N-[(1S)-1-{[(2S)-4-($l^{5},-diazynylidene)-3-oxo-1-phenylbutan-2-yl]carbamoyl}-2-phenylethyl]carbamate

• ChemBase ID: 106496
• Molecular Formular: C27H26N4O4
• Molecular Mass: 470.51974
• Monoisotopic Mass: 470.19540533
• SMILES: [N-]=[N+]=CC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
• Canonical SMILES: [N-]=[N+]=CC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C27H26N4O4/c28-29-18-25(32)23(16-20-10-4-1-5-11-20)30-26(33)24(17-21-12-6-2-7-13-21)31-27(34)35-19-22-14-8-3-9-15-22/h1-15,18,23-24H,16-17,19H2,(H,30,33)(H,31,34)/t23-,24-/m0/s1
• InChIKey: JIFSOVRQDDYNAH-ZEQRLZLVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(1S)-1-{[(2S)-4-($l^{5},-diazynylidene)-3-oxo-1-phenylbutan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• IUPAC Traditional name: benzyl N-[(1S)-1-{[(2S)-4-($l^{5},-diazynylidene)-3-oxo-1-phenylbutan-2-yl]carbamoyl}-2-phenylethyl]carbamate
• Synonyms: Z-Phe-Phe-DMK; Z-FF-DMK; Z-Phe-Phe-Diazomethylketone

Database IDs

• PubChem SID: 162105485
• PubChem CID: 5486921

CALCULATED PROPERTIES

• Acid pKa: 8.971151
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.2709548
• LogD (pH = 7.4): 3.2683551
• Log P: 3.270989
• Molar Refractivity: 129.8201 cm^3
• Polarizability: 50.55703 Å^3
• Polar Surface Area: 101.57 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03DK002

A Cysteine protease inhibitor for Cathepsin L.

REFERENCES

• Green, C.D.J. and Shaw, E., J. Biol. Chem., 256:1923 (1981).
• Kirscke, H. and Shaw, E., Biochem. Biophys. Res. Comm., 101:454 (1981).