(4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid

• ChemBase ID: 106351
• Molecular Formular: C31H38F3N5O12
• Molecular Mass: 729.6549296
• Monoisotopic Mass: 729.24690634
• SMILES: CC[C@H](C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[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@H](O)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C31H38F3N5O12/c1-5-13(2)25(35-15(4)41)29(49)37-19(8-9-22(42)43)27(47)39-26(14(3)40)30(50)38-20(12-23(44)45)28(48)36-16-6-7-17-18(31(32,33)34)11-24(46)51-21(17)10-16/h6-7,10-11,13-14,19-20,25-26,40H,5,8-9,12H2,1-4H3,(H,35,41)(H,36,48)(H,37,49)(H,38,50)(H,39,47)(H,42,43)(H,44,45)/t13-,14+,19-,20-,25-,26-/m0/s1
• InChIKey: CGUOWXRXLQXOKO-FCQBACSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• Synonyms: Ac-Ile-Glu-Thr-Asp-AFC; Ac-IGTD-AFC; Ac-Ile-Glu-Thr-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105411
• PubChem CID: 25108570

CALCULATED PROPERTIES

• Acid pKa: 3.5210316
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.039998
• LogD (pH = 7.4): -7.1997724
• Log P: -0.75441796
• Molar Refractivity: 167.2006 cm^3
• Polarizability: 63.7484 Å^3
• Polar Surface Area: 266.63 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC140

A fluorogenic substrate for the detection of granzyme B and caspase-8 activity. 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

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).
• Karahashi, H., and Amano, F. 2000. Biol. Pharm. Bull. 23, 140.