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

• ChemBase ID: 106532
• Molecular Formular: C21H28FN3O7
• Molecular Mass: 453.4613232
• Monoisotopic Mass: 453.19112847
• SMILES: CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)CF
• Canonical SMILES: FCC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1)C)CC(=O)O
• InChI: InChI=1S/C21H28FN3O7/c1-12(2)18(25-21(31)32-11-14-7-5-4-6-8-14)20(30)23-13(3)19(29)24-15(9-17(27)28)16(26)10-22/h4-8,12-13,15,18H,9-11H2,1-3H3,(H,23,30)(H,24,29)(H,25,31)(H,27,28)/t13-,15-,18-/m0/s1
• InChIKey: SUUHZYLYARUNIA-YEWWUXTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]propanamido]-5-fluoro-4-oxopentanoic acid
• Synonyms: Z-Val-Ala-Asp-FMK; Z-VAD-FMK; Z-Val-Ala-Asp-Fluoromethylketone; Z-VAD-FMK, Non-methylated; Z-Val-Ala-Asp fluoromethyl ketone

Database IDs

• CAS Number: 634911-81-2
• MDL Number: MFCD03452883
• PubChem SID: 162087211
• PubChem CID: 5497171

CALCULATED PROPERTIES

• Acid pKa: 4.1306753
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.22448704
• LogD (pH = 7.4): -1.9194105
• Log P: 1.1600142
• Molar Refractivity: 109.3643 cm^3
• Polarizability: 42.778816 Å^3
• Polar Surface Area: 150.9 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: 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 - 03FK109

An irreversible general caspase inhibitor, non-methylated form.PROTECT FROM MOISTURE. Useful for studies involving recombinant, isolated, and purified caspase enzymes. Unlike Z-VAD(OMe)-FMK (Cat. No. FK009), this inhibitor does not require pretreatment with esterase for in vitro studies.

Sigma Aldrich - C2105

Amino Acid Sequence
Z-Val-Ala-Asp-OMe-FMK
Biochem/physiol Actions
Non-methylated competitive and irreversible inhibitor of caspase-1, as well as other caspases, which can be used directly with purified enzymes. It does not require esterase to hydrolyze the O-methyl ester like the cell-permeable form, Z-Val-Ala-Asp(OMe) fluoromethyl ketone (Product Code V-116).

REFERENCES

• Komoriya, A. et al., J. Exp. Med., 191:1819 (2000).
• Weissner, C. et al., Cell. Mol. Biol., 46:53 (2000).
• Misaghi, S., et al. 2004. Chem. Biol. 11, 1677.