methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-4-carbamoylbutanamido]-4-(methylsulfanyl)butanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106519
• Molecular Formular: C29H40FN5O11S
• Molecular Mass: 685.7182032
• Monoisotopic Mass: 685.24290635
• SMILES: COC(=O)C[C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)OC)NC(=O)OCc1ccccc1)C(=O)CF
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(=O)OC)CCC(=O)N
• InChI: InChI=1S/C29H40FN5O11S/c1-44-24(38)13-20(22(36)15-30)34-27(41)19(11-12-47-3)33-26(40)18(9-10-23(31)37)32-28(42)21(14-25(39)45-2)35-29(43)46-16-17-7-5-4-6-8-17/h4-8,18-21H,9-16H2,1-3H3,(H2,31,37)(H,32,42)(H,33,40)(H,34,41)(H,35,43)/t18-,19-,20-,21-/m0/s1
• InChIKey: QFITYVNVMNJELE-TUFLPTIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-4-carbamoylbutanamido]-4-(methylsulfanyl)butanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methoxy-4-oxobutanamido]-4-carbamoylbutanamido]-4-(methylsulfanyl)butanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Asp(OMe)-Gln-Met-Asp(OMe)-FMK; Z-D(OMe)QMD(OMe)-FMK; Z-Asp(OMe)-Gln-Met-Asp(OMe)-Fluoromethylketone; Z-Asp(OMe)-Gln-Met-Asp(OMe) fluoromethyl ketone

Database IDs

• MDL Number: MFCD03452876
• PubChem SID: 162089027
• PubChem CID: 644197

CALCULATED PROPERTIES

• Acid pKa: 11.412848
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.1226894
• LogD (pH = 7.4): -1.1227262
• Log P: -1.1226889
• Molar Refractivity: 162.941 cm^3
• Polarizability: 64.16699 Å^3
• Polar Surface Area: 238.39 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Shipped in: dry ice

DETAILS

MP Biomedicals - 03FK025

A potent, cell-permeable, and irreversible inhibitor of caspase-3, also recognizes caspase-1. When using with purified native or recombinant enzyme, pre-treatment with an esterase is required.

Sigma Aldrich - C0480

Amino Acid Sequence
Z-Asp-OMe-Gln-Met-Asp-OMe-FMK
Biochem/physiol Actions
A cell-permeable inhibitor of caspase 3 and 6, which exhibits competitive and irreversible inhibition.

REFERENCES

• Hirata, H. et al., J. Exp. Med., 187(4):587(1998).
• Talanian, R.V., et al. 1997. J. Biol. Chem. 272, 9677.