1-fluoromethyl 4-methyl (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]butanedioate

• ChemBase ID: 106504
• Molecular Formular: C30H41FN4O13
• Molecular Mass: 684.6639432
• Monoisotopic Mass: 684.26541561
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CC(=O)OC)NC(=O)OCc1ccccc1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)OC)C(=O)OCF
• Canonical SMILES: FCOC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(=O)OC)CCC(=O)OC)CC(=O)OC
• InChI: InChI=1S/C30H41FN4O13/c1-17(2)25(28(41)33-21(14-24(38)46-5)29(42)48-16-31)35-26(39)19(11-12-22(36)44-3)32-27(40)20(13-23(37)45-4)34-30(43)47-15-18-9-7-6-8-10-18/h6-10,17,19-21,25H,11-16H2,1-5H3,(H,32,40)(H,33,41)(H,34,43)(H,35,39)/t19-,20-,21-,25-/m0/s1
• InChIKey: XINKNBMIVAEBNP-UKDJSQQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-fluoromethyl 4-methyl (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]butanedioate
• IUPAC Traditional name: 1-fluoromethyl 4-methyl (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]butanedioate
• Synonyms: Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-FMK; Z-D(OMe)E(OMe)VD(OMe)-FMK; Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162105708
• PubChem CID: 25108680

CALCULATED PROPERTIES

• Acid pKa: 11.159414
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.011031594
• LogD (pH = 7.4): -0.011097701
• Log P: -0.01103075
• Molar Refractivity: 158.7236 cm^3
• Polarizability: 63.27368 Å^3
• Polar Surface Area: 230.83 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK010

A potent, cell-permeable, and irreversible inhibitor of caspase-3 as well as caspase-6, caspase-7, caspase-8, and caspase-10. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.

REFERENCES

• Chandler, J.M. et al., J. Biol. Chem., 273(18):10815 (1998).
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Masuda, Y., et al. 1997. Biochem. Biophys. Res. Commun. 234, 641.
• Nicholson, D.W. 1996. Nature Biotech. 14, 297.
• Schlegel, J., et al. 1996. J. Biol. Chem. 271, 1841.
• Nicholson, D.W., et al. 1995. Nature 376, 37.