(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)-2-acetamido-4-methylpentanamido]butanoic acid

• ChemBase ID: 106360
• Molecular Formular: C31H38F3N5O12
• Molecular Mass: 729.6549296
• Monoisotopic Mass: 729.24690634
• SMILES: CC(C)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[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/c1-13(2)9-20(35-15(4)41)29(49)37-19(7-8-23(42)43)27(47)39-26(14(3)40)30(50)38-21(12-24(44)45)28(48)36-16-5-6-17-18(31(32,33)34)11-25(46)51-22(17)10-16/h5-6,10-11,13-14,19-21,26,40H,7-9,12H2,1-4H3,(H,35,41)(H,36,48)(H,37,49)(H,38,50)(H,39,47)(H,42,43)(H,44,45)/t14-,19+,20+,21+,26+/m1/s1
• InChIKey: KTZOWCXXAYFIFT-WSQGYFMSSA-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)-2-acetamido-4-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)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Thr-Asp-AFC; Ac-LGlutD-AFC; Ac-Leu-Glu-Thr-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105414
• PubChem CID: 25108579

CALCULATED PROPERTIES

• Acid pKa: 3.4834578
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.2293377
• LogD (pH = 7.4): -7.34378
• Log P: -0.8323717
• Molar Refractivity: 167.2776 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 - 03AFC157

A fluorogenic substrate for Caspase-8.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).