(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-methylbutanamido]butanoic acid

• ChemBase ID: 106363
• Molecular Formular: C32H36F3N7O11
• Molecular Mass: 751.6637496
• Monoisotopic Mass: 751.24248967
• SMILES: CC(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: 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](C(C)C)NC(=O)C)CCC(=O)O)Cc1nc[nH]c1
• InChI: InChI=1S/C32H36F3N7O11/c1-14(2)27(38-15(3)43)31(52)40-20(6-7-24(44)45)28(49)41-21(8-17-12-36-13-37-17)30(51)42-22(11-25(46)47)29(50)39-16-4-5-18-19(32(33,34)35)10-26(48)53-23(18)9-16/h4-5,9-10,12-14,20-22,27H,6-8,11H2,1-3H3,(H,36,37)(H,38,43)(H,39,50)(H,40,52)(H,41,49)(H,42,51)(H,44,45)(H,46,47)/t20-,21-,22-,27-/m0/s1
• InChIKey: GWQXSBZVMCUPKL-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-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-methylbutanamido]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-methylbutanamido]butanoic acid
• Synonyms: Ac-Val-Glu-His-Asp-AFC; Ac-VEHD-AFC; Ac-Val-Glu-His-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105416
• PubChem CID: 25108582

CALCULATED PROPERTIES

• Acid pKa: 3.4237025
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -3.7036204
• LogD (pH = 7.4): -6.270059
• Log P: -2.4266734
• Molar Refractivity: 173.6331 cm^3
• Polarizability: 65.8293 Å^3
• Polar Surface Area: 275.08 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC170

A fluorogenic substrate for Caspase-1.