(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid

• ChemBase ID: 106349
• Molecular Formular: C30H34F3N5O13
• Molecular Mass: 729.6118696
• Monoisotopic Mass: 729.21052083
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=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: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(=O)O)CCC(=O)O
• InChI: InChI=1S/C30H34F3N5O13/c1-12(2)25(38-26(47)17(6-7-21(40)41)36-28(49)18(10-22(42)43)34-13(3)39)29(50)37-19(11-23(44)45)27(48)35-14-4-5-15-16(30(31,32)33)9-24(46)51-20(15)8-14/h4-5,8-9,12,17-19,25H,6-7,10-11H2,1-3H3,(H,34,39)(H,35,48)(H,36,49)(H,37,50)(H,38,47)(H,40,41)(H,42,43)(H,44,45)/t17-,18-,19-,25-/m0/s1
• InChIKey: GZDRODOYEFEHGG-NUDCOPPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Asp-Glu-Val-Asp-AFC; Ac-DEVD-AFC; Ac-Asp-Glu-Val-Asp-7-Amino-4-trifluoromethylcoumarin; N-Acetyl-Asp-Glu-Val-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• CAS Number: 201608-14-2
• MDL Number: MFCD01310970
• PubChem SID: 162087205
• PubChem CID: 644234

CALCULATED PROPERTIES

• Acid pKa: 3.3861065
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -6.030276
• LogD (pH = 7.4): -10.821213
• Log P: -1.2104636
• Molar Refractivity: 162.6725 cm^3
• Polarizability: 61.966278 Å^3
• Polar Surface Area: 283.7 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CASP3(836)

Product Information

• Purity: ≥90% (HPLC)

DETAILS

MP Biomedicals - 03AFC138

A fluorogenic substrate for Caspase-3 (CPP32, YAMA). Also acts as a substrate for granzyme B-processed caspase-6, caspase-7, caspase-8, and caspase-10.
Excitation max.: ~400 nm, Emission max.: ~505 nm

Sigma Aldrich - A0466

Amino Acid Sequence
NAc-Asp-Glu-Val-Asp-AFC
Biochem/physiol Actions
A fluorogenic substrate for caspase 3, a protease that is rapidly activated when cells are exposed to apoptotic conditions and that cleaves poly(ADP-ribose) polymerase. The 7-amido-4-trifluoromethylcoumarin derivative has better membrane permeability than the 7-amido-4-methylcoumarin derivative (A1086).

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Nicholson, D.W. et al., Nature, 376:37 (1995).
• Keramaris, E., et al. 2000. Mol. Cell Neurosci. 15, 368.