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

• ChemBase ID: 106449
• Molecular Formular: C32H43N5O11
• Molecular Mass: 673.71072
• Monoisotopic Mass: 673.29590722
• 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
• 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)C(C)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C32H43N5O11/c1-15(2)11-22(33-18(6)38)31(46)35-21(9-10-25(39)40)29(44)37-28(16(3)4)32(47)36-23(14-26(41)42)30(45)34-19-7-8-20-17(5)12-27(43)48-24(20)13-19/h7-8,12-13,15-16,21-23,28H,9-11,14H2,1-6H3,(H,33,38)(H,34,45)(H,35,46)(H,36,47)(H,37,44)(H,39,40)(H,41,42)/t21-,22-,23-,28-/m0/s1
• InChIKey: KRMSDTWDUCWACW-AMZZYFJHSA-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-methylpropyl]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-methylpropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Val-Asp-AMC; Ac-LEVD-AMC; Ac-Leu-Glu-Val-Asp-7-Amino-4-Methylcoumarin

Database IDs

• PubChem SID: 162105462
• PubChem CID: 25108636

CALCULATED PROPERTIES

• Acid pKa: 3.6191232
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -2.8218174
• LogD (pH = 7.4): -6.0605626
• Log P: 0.32103136
• Molar Refractivity: 169.3782 cm^3
• Polarizability: 65.37238 Å^3
• Polar Surface Area: 246.4 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC155

A 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).