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

• ChemBase ID: 106517
• Molecular Formular: C30H43FN4O11
• Molecular Mass: 654.6810232
• Monoisotopic Mass: 654.29123644
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C(=O)N[C@@H]([C@@H](C)O)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](O)C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C30H43FN4O11/c1-17(2)13-22(34-30(43)46-16-19-9-7-6-8-10-19)28(41)32-20(11-12-24(38)44-4)27(40)35-26(18(3)36)29(42)33-21(23(37)15-31)14-25(39)45-5/h6-10,17-18,20-22,26,36H,11-16H2,1-5H3,(H,32,41)(H,33,42)(H,34,43)(H,35,40)/t18-,20+,21+,22+,26+/m1/s1
• InChIKey: ARECPHKVCIQJRJ-XGRWUTGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-methoxy-5-oxopentanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanamido]-5-methoxy-5-oxopentanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Leu-Glu(OMe)-Thr-Asp(OMe)-FMK; Z-LE(OMe)TD(OMe)-FMK; Z-Leu-Glu(OMe)-Thr-Asp(OMe)-Fluoromethylketone; Z-LETD-FMK; Z-Leu-Glu(OMe)-Thr-Asp(OMe)-fluoromethyl ketone

Database IDs

• MDL Number: MFCD03452906
• PubChem SID: 162105506
• PubChem CID: 25108688

CALCULATED PROPERTIES

• Acid pKa: 11.223258
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.2984118
• LogD (pH = 7.4): 0.29835472
• Log P: 0.2984125
• Molar Refractivity: 157.6308 cm^3
• Polarizability: 62.295883 Å^3
• Polar Surface Area: 215.53 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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)
• Empirical Formula (Hill Notation): C30H44N4O11F

DETAILS

MP Biomedicals - 03FK023

An inhibitor for Caspase-8.

Sigma Aldrich - C8734

Amino Acid Sequence
Z-Leu-Glu(OMe)-Thr-Asp(OMe)-FMK
Application
Cell permeable caspase-8 inhibitor.

REFERENCES

• Nicholson, D.W., and Thornberry, N.A., Caspases:killer proteases. Trends. Biochem. Sci., 22, 299(1997).
• Cohen, G.M., Caspases: the executioners ofapoptosis. Biochem. J., 326, 1 (1997).
• Fernandes-Alnemri, T., et al., In vitro activation ofCPP32 and Mch3 by Mch4, a novel humanapoptotic cysteine protease containing two FADDlikedomains. Proc. Natl. Acad. Sci. USA, 93, 7464-7469 (1996).
• Srinivasula, S.M., et al., Molecular ordering of theFas-apoptotic pathway: the Fas/APO-1 proteaseMch5 is a CrmA-inhibitable protease that activatesmultiple Ced-3/ICE-like cysteine proteases. ProcNatl Acad Sci USA, 93, 14486-14491 (1996).
• Thornberry, N. et al., Science, 281:1312 (1998).