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

• ChemBase ID: 106352
• Molecular Formular: C32H40F3N5O11
• Molecular Mass: 727.6821096
• Monoisotopic Mass: 727.26764179
• SMILES: CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](NC(=O)C)C(C)C)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)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CCC(=O)O)C
• InChI: InChI=1S/C32H40F3N5O11/c1-6-15(4)27(40-28(47)20(9-10-23(42)43)38-30(49)26(14(2)3)36-16(5)41)31(50)39-21(13-24(44)45)29(48)37-17-7-8-18-19(32(33,34)35)12-25(46)51-22(18)11-17/h7-8,11-12,14-15,20-21,26-27H,6,9-10,13H2,1-5H3,(H,36,41)(H,37,48)(H,38,49)(H,39,50)(H,40,47)(H,42,43)(H,44,45)/t15-,20-,21-,26-,27-/m0/s1
• InChIKey: RPBOFHGWCDGAEG-OIOUIRQFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105619
• PubChem CID: 25108571

CALCULATED PROPERTIES

• Acid pKa: 3.67373
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -2.2467408
• LogD (pH = 7.4): -5.533552
• Log P: 0.7634122
• Molar Refractivity: 170.2337 cm^3
• Polarizability: 64.851204 Å^3
• Polar Surface Area: 246.4 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC141

A fluorogenic substrate for Caspase-6.

REFERENCES

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