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

• ChemBase ID: 106497
• Molecular Formular: C21H22N4O4
• Molecular Mass: 394.42378
• Monoisotopic Mass: 394.1641052
• SMILES: C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)C=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=CC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C21H22N4O4/c1-15(19(26)13-23-22)24-20(27)18(12-16-8-4-2-5-9-16)25-21(28)29-14-17-10-6-3-7-11-17/h2-11,13,15,18H,12,14H2,1H3,(H,24,27)(H,25,28)/t15-,18-/m0/s1
• InChIKey: QMPATRQNERZOMF-YJBOKZPZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105486
• PubChem CID: 5488522

CALCULATED PROPERTIES

• Acid pKa: 8.971524
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.6146286
• LogD (pH = 7.4): 1.6120309
• Log P: 1.6146625
• Molar Refractivity: 105.2011 cm^3
• Polarizability: 40.984028 Å^3
• Polar Surface Area: 101.57 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03DK003

An inhibitor for Cathepsin B.

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).