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

• ChemBase ID: 106448
• Molecular Formular: C33H41N7O11
• Molecular Mass: 711.71894
• Monoisotopic Mass: 711.28640517
• 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
• 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)CC(=O)O)Cc1nc[nH]c1)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C33H41N7O11/c1-16(2)9-23(36-18(4)41)32(49)38-22(7-8-27(42)43)30(47)39-24(11-20-14-34-15-35-20)33(50)40-25(13-28(44)45)31(48)37-19-5-6-21-17(3)10-29(46)51-26(21)12-19/h5-6,10,12,14-16,22-25H,7-9,11,13H2,1-4H3,(H,34,35)(H,36,41)(H,37,48)(H,38,49)(H,39,47)(H,40,50)(H,42,43)(H,44,45)/t22-,23-,24-,25-/m0/s1
• InChIKey: ZILMZAQLFLKJPG-QORCZRPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-methyl-2-oxo-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-[(4-methyl-2-oxochromen-7-yl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-His-Asp-AMC; Ac-LEHD-AMC; Ac-Leu-Glu-His-Asp-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105461
• PubChem CID: 25108635

CALCULATED PROPERTIES

• Acid pKa: 3.3879657
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -3.8040745
• LogD (pH = 7.4): -6.3336487
• Log P: -2.4741423
• Molar Refractivity: 177.3786 cm^3
• Polarizability: 68.14479 Å^3
• Polar Surface Area: 275.08 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC154

A fluorogenic substrate for Caspase-9.

REFERENCES

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