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

• ChemBase ID: 106525
• Molecular Formular: C32H45FN4O12
• Molecular Mass: 696.7177032
• Monoisotopic Mass: 696.30180112
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CCC(=O)OC)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)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)CCC(=O)OC)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C32H45FN4O12/c1-19(2)15-24(37-32(45)49-18-20-9-7-6-8-10-20)31(44)35-21(11-13-26(39)46-3)29(42)34-22(12-14-27(40)47-4)30(43)36-23(25(38)17-33)16-28(41)48-5/h6-10,19,21-24H,11-18H2,1-5H3,(H,34,42)(H,35,44)(H,36,43)(H,37,45)/t21-,22-,23-,24-/m0/s1
• InChIKey: JQWJGEBRHHCICO-ZJZGAYNASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD03453602
• PubChem SID: 162105509
• PubChem CID: 25108692

CALCULATED PROPERTIES

• Acid pKa: 11.3659525
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.72149026
• LogD (pH = 7.4): 0.7214492
• Log P: 0.7214908
• Molar Refractivity: 167.2278 cm^3
• Polarizability: 66.1528 Å^3
• Polar Surface Area: 221.6 Å^2
• Rotatable Bonds: 25
• 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

Product Information

• Purity: ≥90% (TLC)
• Empirical Formula (Hill Notation): C32H45FN4O12

DETAILS

MP Biomedicals - 03FK030

A cell-permeable, irreversible inhibitor of caspase-13. When using with purified native or recombinant enzyme, pretreatment with an esterase is required.

Sigma Aldrich - C8859

Amino Acid Sequence
Z-Leu-Glu(OMe)-Glu(OMe)-Asp(OMe)-FMK
Application
Cell permeable Caspase-13 inhibitor.

REFERENCES

• Humke, E.W. et al., J. Biol. Chem., 273(25):15702 (1998).