(4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid

• ChemBase ID: 106642
• Molecular Formular: C27H38N6O12
• Molecular Mass: 638.62362
• Monoisotopic Mass: 638.25477069
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)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)[C@H](O)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C27H38N6O12/c1-13(2)11-19(28-15(4)35)26(42)30-18(9-10-21(36)37)24(40)32-23(14(3)34)27(43)31-20(12-22(38)39)25(41)29-16-5-7-17(8-6-16)33(44)45/h5-8,13-14,18-20,23,34H,9-12H2,1-4H3,(H,28,35)(H,29,41)(H,30,42)(H,31,43)(H,32,40)(H,36,37)(H,38,39)/t14-,18+,19+,20+,23+/m1/s1
• InChIKey: OJBHIXURHJXQSR-XUQLPURUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Thr-Asp-PNA; Ac-LETD-PNA; Ac-Leu-Glu-Thr-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105996
• PubChem CID: 25108791

CALCULATED PROPERTIES

• Acid pKa: 3.4258838
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -4.8464046
• LogD (pH = 7.4): -7.9091406
• Log P: -1.366323
• Molar Refractivity: 153.8972 cm^3
• Polarizability: 58.987675 Å^3
• Polar Surface Area: 286.15 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA157

A colorimetric substrate for Caspase-8.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).