(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid

• ChemBase ID: 106362
• Molecular Formular: C29H34F3N5O12S
• Molecular Mass: 733.6667696
• Monoisotopic Mass: 733.18767721
• SMILES: CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)O)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CSCC[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](NC(=O)C)CCC(=O)O)CO
• InChI: InChI=1S/C29H34F3N5O12S/c1-13(39)33-17(5-6-22(40)41)25(45)37-20(12-38)28(48)35-18(7-8-50-2)26(46)36-19(11-23(42)43)27(47)34-14-3-4-15-16(29(30,31)32)10-24(44)49-21(15)9-14/h3-4,9-10,17-20,38H,5-8,11-12H2,1-2H3,(H,33,39)(H,34,47)(H,35,48)(H,36,46)(H,37,45)(H,40,41)(H,42,43)/t17-,18-,19-,20-/m0/s1
• InChIKey: DIDNSYMQNBNHNW-MUGJNUQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-4-acetamidobutanoic acid
• Synonyms: Ac-Glu-Ser-Met-Asp-AFC; Ac-ESMD-AFC; Ac-Glu-Ser-Met-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105415
• PubChem CID: 25108581

CALCULATED PROPERTIES

• Acid pKa: 3.5165424
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.154331
• LogD (pH = 7.4): -8.308114
• Log P: -1.8516285
• Molar Refractivity: 166.2739 cm^3
• Polarizability: 63.190006 Å^3
• Polar Surface Area: 266.63 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC169

A fluorogenic substrate for Caspase-3.

REFERENCES

• Han, Z. et al., J. Biol. Chem., 272:13432 (1997).