(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-3-(1H-indol-3-yl)propanamido]butanoic acid

• ChemBase ID: 106359
• Molecular Formular: C38H37F3N8O11
• Molecular Mass: 838.7425896
• Monoisotopic Mass: 838.2533887
• SMILES: CC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)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: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)C)CCC(=O)O)Cc1nc[nH]c1
• InChI: InChI=1S/C38H37F3N8O11/c1-18(50)45-27(10-19-15-43-25-5-3-2-4-22(19)25)36(58)47-26(8-9-31(51)52)34(56)48-28(11-21-16-42-17-44-21)37(59)49-29(14-32(53)54)35(57)46-20-6-7-23-24(38(39,40)41)13-33(55)60-30(23)12-20/h2-7,12-13,15-17,26-29,43H,8-11,14H2,1H3,(H,42,44)(H,45,50)(H,46,57)(H,47,58)(H,48,56)(H,49,59)(H,51,52)(H,53,54)/t26-,27-,28-,29-/m0/s1
• InChIKey: NEGOLAGPKZGIKJ-DZUOILHNSA-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-3-(1H-indol-3-yl)propanamido]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-3-(1H-indol-3-yl)propanamido]butanoic acid
• Synonyms: N-Acetyl-Trp-Glu-His-Asp-7-amido-4-trifluoromethylcoumarin trifluoroacetate salt; Ac-Trp-Glu-His-Asp-AFC; Ac-WEHD-AFC; Ac-Trp-Glu-His-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• MDL Number: MFCD01862607
• PubChem SID: 162105413
• PubChem CID: 25108578

CALCULATED PROPERTIES

• Acid pKa: 3.4063892
• H Acceptors: 11
• H Donor: 9
• LogD (pH = 5.5): -2.8770258
• LogD (pH = 7.4): -5.429512
• Log P: -1.5786666
• Molar Refractivity: 200.343 cm^3
• Polarizability: 76.69295 Å^3
• Polar Surface Area: 290.87 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO/DMF: soluble20 mM
• Apperance: yellow 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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03AFC156

A fluorogenic substrate for caspase-5 (ICErel-III, TY), caspase-1, and caspase-4. 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 - A6720

Biochem/physiol Actions
Fluorogenic substrate for caspase 1 and 5.

REFERENCES

• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997).
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.