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

• ChemBase ID: 106520
• Molecular Formular: C31H45FN4O10
• Molecular Mass: 652.7082032
• Monoisotopic Mass: 652.31197188
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C(=O)N[C@@H](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(C)C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C
• InChI: InChI=1S/C31H45FN4O10/c1-18(2)14-23(35-31(43)46-17-20-10-8-7-9-11-20)29(41)33-21(12-13-25(38)44-5)28(40)36-27(19(3)4)30(42)34-22(24(37)16-32)15-26(39)45-6/h7-11,18-19,21-23,27H,12-17H2,1-6H3,(H,33,41)(H,34,42)(H,35,43)(H,36,40)/t21-,22-,23-,27-/m0/s1
• InChIKey: WGJLXPZGHLANRB-FAWUNYRSSA-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]-3-methylbutanamido]-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]-3-methylbutanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Leu-Glu(OMe)-Val-Asp(OMe)-FMK; Z-LE(OMe)VD(OMe)-FMK; Z-Leu-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162105507
• PubChem CID: 25108689

CALCULATED PROPERTIES

• Acid pKa: 11.45317
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.8162422
• LogD (pH = 7.4): 1.8162086
• Log P: 1.8162427
• Molar Refractivity: 160.6639 cm^3
• Polarizability: 63.43836 Å^3
• Polar Surface Area: 195.3 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK026

An inhibitor for Caspase-4.

REFERENCES

• Talanian, R.V. et al., J. Biol. Chem., 272(15):9677 (1997).