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

• ChemBase ID: 106639
• Molecular Formular: C29H38N8O11
• Molecular Mass: 674.65902
• Monoisotopic Mass: 674.26600408
• 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)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)Cc1nc[nH]c1)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C29H38N8O11/c1-15(2)10-21(32-16(3)38)28(45)34-20(8-9-24(39)40)26(43)35-22(11-18-13-30-14-31-18)29(46)36-23(12-25(41)42)27(44)33-17-4-6-19(7-5-17)37(47)48/h4-7,13-15,20-23H,8-12H2,1-3H3,(H,30,31)(H,32,38)(H,33,44)(H,34,45)(H,35,43)(H,36,46)(H,39,40)(H,41,42)/t20-,21-,22-,23-/m0/s1
• InChIKey: SHOGFKLEAOHMOJ-MLCQCVOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)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-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-His-Asp-PNA; Ac-LEHD-PNA; Ac-Leu-Glu-His-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105726
• PubChem CID: 25108788

CALCULATED PROPERTIES

• Acid pKa: 3.3133461
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -4.0134764
• LogD (pH = 7.4): -6.5265307
• Log P: -2.6751118
• Molar Refractivity: 164.9307 cm^3
• Polarizability: 62.894276 Å^3
• Polar Surface Area: 294.6 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA154

A colorimetric substrate for Caspase-9. Cleavage is monitored colorimetrically at ~405 nm.

REFERENCES

• Harris, J.L. et al., J. Biol. Chem., 273:27364 (1998).
• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Thornberry, N.A., et al. 1997. J. Biol. Chem. 272, 17907.