methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106513
• Molecular Formular: C38H60FN7O13S
• Molecular Mass: 873.9855032
• Monoisotopic Mass: 873.39538424
• SMILES: CC([C@@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCCCCNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)CC(=O)OC)CCC(=O)OC)C
• Canonical SMILES: COC(=O)C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)C(C)C)CCC(=O)OC)NC(=O)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C38H60FN7O13S/c1-21(2)33(37(55)43-23(26(47)19-39)17-31(51)58-4)45-35(53)22(14-15-30(50)57-3)42-36(54)24(18-32(52)59-5)41-29(49)13-7-6-10-16-40-28(48)12-9-8-11-27-34-25(20-60-27)44-38(56)46-34/h21-25,27,33-34H,6-20H2,1-5H3,(H,40,48)(H,41,49)(H,42,54)(H,43,55)(H,45,53)(H2,44,46,56)/t22-,23-,24-,25-,27-,33-,34-/m0/s1
• InChIKey: ZRAMQWYBTNBGSD-YCXFPXQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)-4-methoxy-4-oxobutanamido]-5-methoxy-5-oxopentanamido]-3-methylbutanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Biotin-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-FMK; Biotin-D(OMe)E(OMe)VD(OMe)-FMK; Biotin-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162105505
• PubChem CID: 71300129

CALCULATED PROPERTIES

• Acid pKa: 11.362977
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -1.4252543
• LogD (pH = 7.4): -1.4252942
• Log P: -1.4252522
• Molar Refractivity: 210.4257 cm^3
• Polarizability: 83.23365 Å^3
• Polar Surface Area: 282.6 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK019

An inhibitor/probe for Caspases-3. A biotinylated derivative of Caspase-3 inhibitor Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-FMK (Cat. No. FK010) that has been esterified to increase cell permeability. Also inhibits caspase-6, caspase-7, and caspase-10. Can be used to purify caspase-3 from cell lysates. The addition of esterase will enhance inhibitory activity in cell-free systems.

REFERENCES

• Chandler, J. et al., J. Biol. Chem., 273(18):10815 (1998).
• Nicholson, D.W. et al., Nature, 376:37 (1995).