methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106515
• Molecular Formular: C37H42FN7O10
• Molecular Mass: 763.7686832
• Monoisotopic Mass: 763.2977188
• SMILES: COC(=O)CC[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]cn1)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)Cc1nc[nH]c1)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C37H42FN7O10/c1-53-32(47)13-12-27(34(49)44-30(15-24-19-39-21-41-24)36(51)43-28(31(46)17-38)16-33(48)54-2)42-35(50)29(14-23-18-40-26-11-7-6-10-25(23)26)45-37(52)55-20-22-8-4-3-5-9-22/h3-11,18-19,21,27-30,40H,12-17,20H2,1-2H3,(H,39,41)(H,42,50)(H,43,51)(H,44,49)(H,45,52)/t27-,28-,29-,30-/m0/s1
• InChIKey: NLZNSSWGRVBWIX-KRCBVYEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(1H-indol-3-yl)propanamido]-5-methoxy-5-oxopentanamido]-3-(1H-imidazol-4-yl)propanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Trp-Glu(OMe)-His-Asp(OMe)-FMK; Z-WE(OMe)HD(OMe)-FMK; Z-Trp-Glu(OMe)-His-Asp(OMe)-Fluoromethylketone

Database IDs

• PubChem SID: 162106012
• PubChem CID: 25108687

CALCULATED PROPERTIES

• Acid pKa: 11.291196
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 0.21509877
• LogD (pH = 7.4): 0.94708157
• Log P: 0.9974054
• Molar Refractivity: 190.6962 cm^3
• Polarizability: 75.35483 Å^3
• Polar Surface Area: 239.77 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03FK021

A potent, cell-permeable, and irreversible inhibitor of caspase-5. Strongly inhibits caspase-1. Also inhibits caspase-4 and caspase-8. HYGROSCOPIC. KEEP DESICCATED.

REFERENCES

• Garcia-Calvo, M., et al. 1998. J. Biol. Chem. 273, 32608.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Rano, T., et al. 1997. Chem. Biol. 4, 149.