methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate

• ChemBase编号: 106503
• 分子式: C22H30FN3O7
• 平均质量: 467.4879032
• 单一同位素质量: 467.20677854
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)CF
• Canonical SMILES: COC(=O)C[C@@H](C(=O)CF)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C22H30FN3O7/c1-13(2)19(26-22(31)33-12-15-8-6-5-7-9-15)21(30)24-14(3)20(29)25-16(17(27)11-23)10-18(28)32-4/h5-9,13-14,16,19H,10-12H2,1-4H3,(H,24,30)(H,25,29)(H,26,31)/t14-,16-,19-/m0/s1
• InChIKey: MIFGOLAMNLSLGH-QOKNQOGYSA-N

名称和登记号

名称

• IUPAC标准名: methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• IUPAC传统名: methyl (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoate
• 别名: Z-Val-Ala-Asp-(OMe)-FMK; Z-VAD(OMe)-FMK; Z-VAL-ALA-ASP-(OME)-FLUOROMETHYLKETONE

登记号

• PubChem SID: 162105502
• PubChem CID: 5497174

理论计算性质

• Acid pKa: 11.600033
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.3059078
• LogD (pH = 7.4): 1.3058839
• Log P: 1.3059082
• 摩尔折射率: 114.1334 cm^3
• 极化性: 44.83733 Å^3
• 极化表面积: 139.9 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: true

详细说明

MP Biomedicals - 03FK009

The Z-VAD-FMK (carbobenzoxy-valyl-alanyl-aspartyl-[O-methyl]- fluoromethylketone) is a cell-permeant pan caspase inhibitor that irreversibly binds to the catalytic site of caspase proteases and can inhibit induction of apoptosis.
Apoptosis is a physiological form of cell death, which plays important role in embrogenesis, cellular homoestasis, tisue atropy, and removal damaged and mutated cells.Caspases, which act act as molecular chainsaw are the central components of apoptosis response. Caspases are cysteine proteases that cleave after aspartate residue in their substrates. At least 7 of 14 known mammalian caspases have important role in apoptosis. For inhibition of apoptosis, Z-VAD-FMK should be added at the same time that apoptosis is induced.
This Z-VAD-FMK peptide is O-methylated in the P1 position on aspartic acid, providing enhanced stability and increased cell permeability. The suggested concentration for use in the anti-Fas mAb-treated Jurkat cell culture model system is 20μM.

参考文献

• Cohen, G. et al., Biochem., 326:1 (1997).