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

• ChemBase ID: 106358
• Molecular Formular: C32H40F3N5O11
• Molecular Mass: 727.6821096
• Monoisotopic Mass: 727.26764179
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](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[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(C)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C32H40F3N5O11/c1-14(2)10-21(36-16(5)41)30(49)38-20(8-9-24(42)43)28(47)40-27(15(3)4)31(50)39-22(13-25(44)45)29(48)37-17-6-7-18-19(32(33,34)35)12-26(46)51-23(18)11-17/h6-7,11-12,14-15,20-22,27H,8-10,13H2,1-5H3,(H,36,41)(H,37,48)(H,38,49)(H,39,50)(H,40,47)(H,42,43)(H,44,45)/t20-,21-,22-,27-/m0/s1
• InChIKey: FETZKXHXYOHAAN-LFYAFONDSA-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)-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-methylpropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Val-Asp-AFC; Ac-LEVD-AFC; Ac-Leu-Glu-Val-Asp-7-Amino-4-trifluoromethylcoumarin; N-Acetyl-Leu-Glu-Val-Asp-7-amido-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD01862605
• PubChem SID: 162105693
• PubChem CID: 25108577

CALCULATED PROPERTIES

• Acid pKa: 3.5976512
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -2.4897501
• LogD (pH = 7.4): -5.7115684
• Log P: 0.6854585
• Molar Refractivity: 170.3107 cm^3
• Polarizability: 64.851204 Å^3
• Polar Surface Area: 246.4 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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: rat ... Prkcq(85420)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C32H40N5O11F3

DETAILS

MP Biomedicals - 03AFC155

A fluorogenic substrate for Caspase-4 (ICErel-II, TX, ICH-2). Reaction can be monitored visually or quantitatively by a blue to green shift in fluorescence upon cleavage of the AFC fluorophore. Also serves as a substrate for caspase-1.
Excitation max.: ~400 nm, Emission max.: ~505 nm

Sigma Aldrich - A2099

Amino Acid Sequence
NAc-Leu-Glu-Val-Asp-AFC
Biochem/physiol Actions
Fluorogenic substrate for caspase 4.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).
• Lynch, T., et al. 1997. Mol. Psychiatr. 2, 227.
• Thornberry, N.A., et al. 1997. J. Biol. Chem. 272, 17907.