methyl (3S)-3-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-5-methoxy-5-oxopentanamido]-3-methylpentanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106509
• Molecular Formular: C31H45FN4O10
• Molecular Mass: 652.7082032
• Monoisotopic Mass: 652.31197188
• SMILES: CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C(=O)N[C@@H](CC(=O)OC)C(=O)CF
• Canonical SMILES: COC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)CF)CC(=O)OC)[C@H](CC)C)NC(=O)[C@H](C(C)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C31H45FN4O10/c1-7-19(4)27(30(42)34-22(23(37)16-32)15-25(39)45-6)35-28(40)21(13-14-24(38)44-5)33-29(41)26(18(2)3)36-31(43)46-17-20-11-9-8-10-12-20/h8-12,18-19,21-22,26-27H,7,13-17H2,1-6H3,(H,33,41)(H,34,42)(H,35,40)(H,36,43)/t19-,21-,22-,26-,27-/m0/s1
• InChIKey: YPIHFMWAHMPACV-IREHUOSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-5-methoxy-5-oxopentanamido]-3-methylpentanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido]-5-methoxy-5-oxopentanamido]-3-methylpentanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Val-Glu(OMe)-Ile-Asp(OMe)-FMK; Z-VE(OMe)ID(OMe)-FMK; Z-Val-Glu(OMe)-Ile-Asp(OMe)-Fluoromethylketone; Z-Val-Glu(O-Me)-Ile-Asp(O-Me) fluoromethyl ketone

Database IDs

• MDL Number: MFCD03452882
• PubChem SID: 162087300
• PubChem CID: 25108683

CALCULATED PROPERTIES

• LogD (pH = 7.4): 1.8941619
• Log P: 1.8941964
• Molar Refractivity: 160.5869 cm^3
• Polarizability: 63.43836 Å^3
• Polar Surface Area: 195.3 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false
• Acid pKa: 11.447891
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.8941959

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble20 mM
• 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

• Shipped in: dry ice

DETAILS

MP Biomedicals - 03FK015

A cell-permeable, irreversible inhibitor of caspase-6. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.

Sigma Aldrich - C1730

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

REFERENCES

• Zhuang, S. et al., Am. J. Physiol. Cell. Physiol., 279(2):C341 (2000).
• Gregoli, P.A., and Bondurant, M.C. 1999. J. Cell Physiol. 178, 133.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.