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

• ChemBase ID: 106506
• Molecular Formular: C30H43FN4O11
• Molecular Mass: 654.6810232
• Monoisotopic Mass: 654.29123644
• SMILES: CC[C@H](C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)OC)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]([C@H](CC)C)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C30H43FN4O11/c1-6-17(2)25(35-30(43)46-16-19-10-8-7-9-11-19)28(41)32-20(12-13-23(38)44-4)27(40)34-26(18(3)36)29(42)33-21(22(37)15-31)14-24(39)45-5/h7-11,17-18,20-21,25-26,36H,6,12-16H2,1-5H3,(H,32,41)(H,33,42)(H,34,40)(H,35,43)/t17-,18+,20-,21-,25-,26-/m0/s1
• InChIKey: PHLCQASLWHYEMX-DEKIMQJDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105990
• PubChem CID: 25108681

CALCULATED PROPERTIES

• Acid pKa: 11.206472
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.37636548
• LogD (pH = 7.4): 0.37630615
• Log P: 0.37636623
• Molar Refractivity: 157.5538 cm^3
• Polarizability: 62.295883 Å^3
• Polar Surface Area: 215.53 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK012

A potent, cell-permeable, and irreversible inhibitor of caspase-8 and granzyme B. Effectively inhibits influenza virus-induced apoptosis in HeLa cells. Also inhibits granzyme B. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.

REFERENCES

• Zhuang, S. et al., Exp. Cell. Res., 250(1):203 (1999).