(2S)-N-[(3S)-1-fluoro-2-oxo-5-phenylpentan-3-yl]-3-methyl-2-[(morpholine-4-carbonyl)amino]butanamide

• ChemBase ID: 106512
• Molecular Formular: C21H30FN3O4
• Molecular Mass: 407.4790032
• Monoisotopic Mass: 407.22203468
• SMILES: CC(C)[C@H](NC(=O)N1CCOCC1)C(=O)N[C@@H](CCc1ccccc1)C(=O)CF
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)N1CCOCC1)CCc1ccccc1
• InChI: InChI=1S/C21H30FN3O4/c1-15(2)19(24-21(28)25-10-12-29-13-11-25)20(27)23-17(18(26)14-22)9-8-16-6-4-3-5-7-16/h3-7,15,17,19H,8-14H2,1-2H3,(H,23,27)(H,24,28)/t17-,19-/m0/s1
• InChIKey: OHIYFORUMMIZOD-HKUYNNGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(3S)-1-fluoro-2-oxo-5-phenylpentan-3-yl]-3-methyl-2-[(morpholine-4-carbonyl)amino]butanamide
• IUPAC Traditional name: (2S)-N-[(3S)-1-fluoro-2-oxo-5-phenylpentan-3-yl]-3-methyl-2-(morpholine-4-carbonylamino)butanamide
• Synonyms: Mu-Val-Homophe-FMK; Mu-V-HomoPhe-FMK; Mu-Val-Homophe-Fluoromethylketone

Database IDs

• PubChem SID: 162105966
• PubChem CID: 25108685

CALCULATED PROPERTIES

• Acid pKa: 12.41553
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9907818
• LogD (pH = 7.4): 1.9907782
• Log P: 1.9907819
• Molar Refractivity: 106.5599 cm^3
• Polarizability: 41.29998 Å^3
• Polar Surface Area: 87.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 03FK018

A potent, cell-permeable, and irreversible inhibitor of calpain. PROTECT FROM MOISTURE.

REFERENCES

• Esser, R. et al., J. of Rheumatology, 20(7):1176 (1993).
• Esser, R.E. et al., Arthritis Rheum., 37(21):236 (1994).