(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid

• ChemBase ID: 105629
• Molecular Formular: C39H40F3N5O11
• Molecular Mass: 811.7570096
• Monoisotopic Mass: 811.26764179
• SMILES: CC(C)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)OCc1ccccc1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1cc2c(cc1)c(cc(=O)o2)C(F)(F)F
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)OCc1ccccc1)C
• InChI: InChI=1S/C39H40F3N5O11/c1-20(2)33(47-36(54)28(15-22-9-12-25(48)13-10-22)46-38(56)57-19-23-7-5-4-6-8-23)37(55)43-21(3)34(52)45-29(18-31(49)50)35(53)44-24-11-14-26-27(39(40,41)42)17-32(51)58-30(26)16-24/h4-14,16-17,20-21,28-29,33,48H,15,18-19H2,1-3H3,(H,43,55)(H,44,53)(H,45,52)(H,46,56)(H,47,54)(H,49,50)/t21-,28-,29-,33-/m0/s1
• InChIKey: QUINXAFKWYKRPT-FNGAAQSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}propanoic acid
• Synonyms: Aminotrifluoromethylcoumarin tetrapeptide conjugate; Z-TYR-VAL-ALA-ASP-AFC; Z-Tyr-Val-Ala-Asp-AFC; Z-YVAD-AFC; Z-Tyr-Val-Ala-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105883
• PubChem CID: 25108563

CALCULATED PROPERTIES

• Acid pKa: 3.6620743
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 1.6455408
• LogD (pH = 7.4): 0.15724443
• Log P: 3.4810243
• Molar Refractivity: 198.6828 cm^3
• Polarizability: 75.38134 Å^3
• Polar Surface Area: 238.56 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)

DETAILS

MP Biomedicals - 02193600

A valuable fluorescent substrate for Interleukin 1 β Converting Enzyme (ICE) ideal for apoptosis research.

MP Biomedicals - 03AFC120Z

A fluorogenic substrate for Caspase-1 (ICE) and Caspase-4. Reaction can be monitored visually or quantitatively by a blue to green shift in fluorescence upon cleavage of the AFC fluorophore.
Excitation max.: ~400 nm, Emission max.: ~505 nm

REFERENCES

• Jones, R.A., et al. 1998. Hepatology 27, 1632.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Walker, N.P., et al. 1994. Cell 78, 343.
• Thornberry, N.A., et al. 1992. Nature 356, 768.