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

• ChemBase ID: 106640
• Molecular Formular: C28H40N6O11
• Molecular Mass: 636.6508
• Monoisotopic Mass: 636.27550613
• 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)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(C)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C28H40N6O11/c1-14(2)12-20(29-16(5)35)27(42)31-19(10-11-22(36)37)25(40)33-24(15(3)4)28(43)32-21(13-23(38)39)26(41)30-17-6-8-18(9-7-17)34(44)45/h6-9,14-15,19-21,24H,10-13H2,1-5H3,(H,29,35)(H,30,41)(H,31,42)(H,32,43)(H,33,40)(H,36,37)(H,38,39)/t19-,20-,21-,24-/m0/s1
• InChIKey: KNKMVACCCNFUDD-CIEVZJJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)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-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Val-Asp-PNA; Ac-LEVD-PNA; Ac-Leu-Glu-Val-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105558
• PubChem CID: 25108789

CALCULATED PROPERTIES

• Acid pKa: 3.5441558
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -3.1008177
• LogD (pH = 7.4): -6.279681
• Log P: 0.15150714
• Molar Refractivity: 156.9303 cm^3
• Polarizability: 60.115948 Å^3
• Polar Surface Area: 265.92 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA155

A colorimetric 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).