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

• ChemBase ID: 106357
• Molecular Formular: C33H38F3N7O11
• Molecular Mass: 765.6903296
• Monoisotopic Mass: 765.25813973
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)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)Cc1nc[nH]c1)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C33H38F3N7O11/c1-15(2)8-22(39-16(3)44)31(52)41-21(6-7-26(45)46)29(50)42-23(9-18-13-37-14-38-18)32(53)43-24(12-27(47)48)30(51)40-17-4-5-19-20(33(34,35)36)11-28(49)54-25(19)10-17/h4-5,10-11,13-15,21-24H,6-9,12H2,1-3H3,(H,37,38)(H,39,44)(H,40,51)(H,41,52)(H,42,50)(H,43,53)(H,45,46)(H,47,48)/t21-,22-,23-,24-/m0/s1
• InChIKey: HULKIXRFKRCRHD-ZJZGAYNASA-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-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: N-Acetyl-Leu-Glu-His-Asp-7-amido-4-trifluoromethylcoumarin; Ac-Leu-Glu-His-Asp-AFC; Ac-LEHD-AFC; Ac-Leu-Glu-His-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD01862610
• PubChem SID: 162087682
• PubChem CID: 25108576

CALCULATED PROPERTIES

• Acid pKa: 3.3691533
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -3.4506953
• LogD (pH = 7.4): -5.9758086
• Log P: -2.1180847
• Molar Refractivity: 178.3111 cm^3
• Polarizability: 67.63715 Å^3
• Polar Surface Area: 275.08 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble20 mM
• 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 ... CARD9(64170), CASP9(842)mouse ... CARD9(332579), CASP9(12371)rat ... CARD9(64171), CASP9(58918)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

MP Biomedicals - 03AFC154

A fluorogenic substrate for Caspase-9 (ICE-LAP6, Mch6). May also act as a substrate for caspase-4 and caspase-5. 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

Sigma Aldrich - A5845

Amino Acid Sequence
NAc-Leu-Glu-His-Asp-AFC
Application
Fluorogenic substrate for caspase 9.

REFERENCES

• Ito, A., et al. 1999. Biochim. Biophys. Acta 1452, 263.
• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997).