(4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-carboxypropanamido]-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}butanoic acid

• ChemBase ID: 106350
• Molecular Formular: C36H38F3N5O14
• Molecular Mass: 821.7072296
• Monoisotopic Mass: 821.23673558
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)OCc1ccccc1)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CC(=O)O)C(C)C)NC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(=O)O
• InChI: InChI=1S/C36H38F3N5O14/c1-17(2)30(34(55)42-23(14-27(47)48)32(53)40-19-8-9-20-21(36(37,38)39)13-29(51)58-25(20)12-19)44-31(52)22(10-11-26(45)46)41-33(54)24(15-28(49)50)43-35(56)57-16-18-6-4-3-5-7-18/h3-9,12-13,17,22-24,30H,10-11,14-16H2,1-2H3,(H,40,53)(H,41,54)(H,42,55)(H,43,56)(H,44,52)(H,45,46)(H,47,48)(H,49,50)/t22-,23-,24-,30-/m0/s1
• InChIKey: JEPURZRNABGOCW-CQUCHYGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-carboxypropanamido]-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-carboxypropanamido]-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}butanoic acid
• Synonyms: Z-Asp-Glu-Val-Asp-AFC; Z-DEVD-AFC; Z-Asp-Glu-Val-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105405
• PubChem CID: 25108569

CALCULATED PROPERTIES

• Acid pKa: 3.3614805
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -3.7644095
• LogD (pH = 7.4): -8.521184
• Log P: 1.1333007
• Molar Refractivity: 188.9087 cm^3
• Polarizability: 72.103874 Å^3
• Polar Surface Area: 292.93 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC138Z

A fluorogenic substrate for Caspase-3 (CPP32, YAMA). Also acts as a substrate for granzyme B-processed ICE-LAP3. Reaction can be monitored by a blue to green shift in fluorescence upon cleavage of the AFC fluorophore. Also a substrate for caspase-6, caspase-7, caspase-8, and caspase-10.
Excitation max.: ~400 nm, Emission max.: ~505 nm

REFERENCES

• Keramaris, E., et al. 2000. Mol. Cell Neurosci. 15, 368.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Kluck, R.M., et al. 1997. Science 275, 1132.
• Talanian, J., et al. 1997. J. Biol. Chem. 272, 9677.
• Chinnaiyan, A.M., et al. 1996. Curr. Biol. 6, 897.
• Nicholson, D.W., et al. 1995. Nature 376, 37.